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May 2025

May 1, 2025Thursday
all-dayWaterfront Playhouse: Wait Until Dark
all-day29th Annual Key West Songwriters Festival
12:00pm - 12:00am3rd Annual I.Care Trash Derby
2:00pm - 5:00pmSBDC at FIU: Florida Keys New Business Launch Lab - Key West
2:00pm - 3:15pmPrime of Life Yoga at the Key West Tropical Forest & Botanical Gardens
3:00pm - 6:00pmHangover Recovery Pool Party
6:00pm - 11:00pmTruman Waterfront Farmers Market
11:30pmRed Barn Theatre Presents: Short Attention Span Theatre 2025 Edition
May 2, 2025Friday
12:00am - 4:00amWaterfront Playhouse: Wait Until Dark
all-day29th Annual Key West Songwriters Festival
all-day3rd Annual I.Care Trash Derby
12:00amRams Head Presents: Nate Smith with Chase Matthew
10:00pm - 1:00amFirst Fridays on Fleming
10:00pm - 11:00pmKey West Yoga Sanctuary: FREE Community Yoga Class/Donation Based
11:30pmRed Barn Theatre Presents: Short Attention Span Theatre 2025 Edition
May 3, 2025Saturday
all-day29th Annual Key West Songwriters Festival
all-day3rd Annual I.Care Trash Derby
2:00pm - 3:15pmPrime of Life Yoga at the Key West Tropical Forest & Botanical Gardens
11:30pmRed Barn Theatre Presents: Short Attention Span Theatre 2025 Edition
May 4, 2025Sunday
12:00am - 2:00am29th Annual Key West Songwriters Festival
12:00am - 12:00pm3rd Annual I.Care Trash Derby
2:00pm - 8:00pmLocals Day at the Key West Tropical Forest & Botanical Garden
4:00pm - 8:00pmSunday Funday Fiesta at the Gates Hotel
May 5, 2025Monday
12:00pm - 12:00amThe Studios of Key West: Havana Art Tour
May 6, 2025Tuesday
all-dayThe Studios of Key West: Havana Art Tour
2:00pm - 3:30pmTourist Development Council: State of the Tourism Industry Meeting Update
2:00pm - 3:00pmStory Time at the Key West Tropical Forest & Botanical Gardens
May 7, 2025Wednesday
all-dayThe Studios of Key West: Havana Art Tour
6:30pmReef Relief Virtual Lesson Series: Marine Ecosystems of the Florida Keys
May 8, 2025Thursday
all-dayThe Studios of Key West: Havana Art Tour
1:00pm - 1:00amSunset Watersports: Mother's Day Weekend Discounted Daily Excursions
3:00pmHistory of Diving Museum: Armed Forces Day Tours
6:00pm - 11:00pmTruman Waterfront Farmers Market
May 9, 2025Friday
12:00am - 12:00pmThe Studios of Key West: Havana Art Tour
12:00pm - 12:00amThe 28th Annual Key West Paddle Classic 2025
1:00pm - 1:00amSunset Watersports: Mother's Day Weekend Discounted Daily Excursions
9:00pm - 1:30amFree Key West Outdoor Movie Night!
9:00pm - 12:30amReef Relief Annual Luau
11:00pmRams Head Presents: Paula Poundstone
May 10, 2025Saturday
12:00am - 12:00pmThe 28th Annual Key West Paddle Classic 2025
1:00pm - 1:00amSunset Watersports: Mother's Day Weekend Discounted Daily Excursions
May 11, 2025Sunday
1:00pm - 1:00amSunset Watersports: Mother's Day Weekend Discounted Daily Excursions
1:00pm - 6:00pmMother's Day Brunch at Four Flamingos, A Richard Blais Key West Kitchen
2:00pm - 7:00pmSeaside Mother’s Day Brunch at One Duval in Key West’s Pier House Resort & Spa
5:00pm - 7:00pmMonroe County Sheriff's Office Animal Farm Open House
9:30pmMother's Day Dinner at Cafe Marquesa
May 12, 2025Monday
1:00amClassic Harbor Line: Full Moon Sail Aboard Schooner America 2.0
1:00pm - 1:00amSunset Watersports: Mother's Day Weekend Discounted Daily Excursions
May 13, 2025Tuesday
1:00amClassic Harbor Line: Full Moon Sail Aboard Schooner America 2.0
2:00pm - 3:00pmStory Time at the Key West Tropical Forest & Botanical Gardens
10:00pmSouthernmost Youth Orchestra Spring Concert
May 15, 2025Thursday
2:30pmReef Relief Virtual Lesson Series: Marine Ecosystems of the Florida Keys
4:00pm - 5:00pmSBDC at FIU: Government Contracting 101 Webinar
6:00pm - 11:00pmTruman Waterfront Farmers Market
10:00pm - 1:00amWalk on White
11:00pm28 Years of Close Up Magic at Schooner Wharf Bar
11:00pmRams Head Presents: Duane Betts & Palmetto Motel
May 16, 2025Friday
4:00pm - 5:00pmSBDC at FIU: Finding and Winning Federal Contracts
May 17, 2025Saturday
12:00pm - 12:00amThe 17th Annual Keys100 Ultramarathon
1:00pm - 4:00pmNative Plant Sale at the Key West Tropical Forest & Botanical Garden
3:00pm - 12:00amHistory of Diving Museum: Admission Specials - Blue Star Museums
11:00pm - 3:00am9th Annual Rotary Club of Key West: Glow Big or Go Home Casino Night
May 18, 2025Sunday
12:00am - 12:00pmThe 17th Annual Keys100 Ultramarathon
all-dayHistory of Diving Museum: Admission Specials - Blue Star Museums
May 19, 2025Monday
all-dayHistory of Diving Museum: Admission Specials - Blue Star Museums
May 20, 2025Tuesday
all-dayHistory of Diving Museum: Admission Specials - Blue Star Museums
2:00pm - 3:00pmStory Time at the Key West Tropical Forest & Botanical Gardens
11:00pmRams Head Presents: Journeyman: Tribute to Eric Clapton
May 21, 2025Wednesday
all-dayHistory of Diving Museum: Admission Specials - Blue Star Museums
2:00pm - 10:45pmHistory of Diving Museum: Admission Specials - Love Our Locals!
11:00pmHistory of Diving Museum: Free Immerse Yourself Presentation - Mistakes Divers Make by Dan Orr
May 22, 2025Thursday
all-dayHistory of Diving Museum: Admission Specials - Blue Star Museums
1:00pm - 1:00amSunset Watersports: Memorial Day Weekend Discounted Daily Excursions
6:00pm - 11:00pmTruman Waterfront Farmers Market
May 23, 2025Friday
all-dayHistory of Diving Museum: Admission Specials - Blue Star Museums
1:00pm - 1:00amSunset Watersports: Memorial Day Weekend Discounted Daily Excursions
May 24, 2025Saturday
all-dayHistory of Diving Museum: Admission Specials - Blue Star Museums
1:00pm - 1:00amSunset Watersports: Memorial Day Weekend Discounted Daily Excursions
May 25, 2025Sunday
all-dayHistory of Diving Museum: Admission Specials - Blue Star Museums
12:30pmThe Marker: The 1st Annual Salute to Service 5K
1:00pm - 1:00amSunset Watersports: Memorial Day Weekend Discounted Daily Excursions
4:00pm34th Annual Schooner Wharf Minimal Regatta
May 26, 2025Monday
all-dayHistory of Diving Museum: Admission Specials - Blue Star Museums
1:00pm - 1:00amSunset Watersports: Memorial Day Weekend Discounted Daily Excursions
May 27, 2025Tuesday
all-dayHistory of Diving Museum: Admission Specials - Blue Star Museums
1:00pm - 1:00amSunset Watersports: Memorial Day Weekend Discounted Daily Excursions
2:00pm - 3:00pmStory Time at the Key West Tropical Forest & Botanical Gardens
May 28, 2025Wednesday
all-dayHistory of Diving Museum: Admission Specials - Blue Star Museums
May 29, 2025Thursday
all-dayHistory of Diving Museum: Admission Specials - Blue Star Museums
2:00pm - 3:30pmTourist Development Council: Hurricane Preparedness Workshop
6:00pm - 11:00pmTruman Waterfront Farmers Market
May 30, 2025Friday
all-dayHistory of Diving Museum: Admission Specials - Blue Star Museums
May 31, 2025Saturday
all-dayHistory of Diving Museum: Admission Specials - Blue Star Museums

Thanks to Our Sponsors

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  • Scholarships

Start: Apr 30th 2:00 PM

End: May 5th 2:00 AM

Various Locations in Key West

X

29th Annual Key West Songwriters Festival

Annual Event

The Key West Songwriters Festival is the largest festival of its kind in the world. It revolves around five days and nights where live music bliss introduces crowds to the faces, voices and stories behind the songs. Performances take place at numerous theaters, bars and event spaces around Key West.

View Event Page

Start: May 1st 11:30 PM

Red Barn Theatre

319 Duval Street

Key West

FL

33040

X

Red Barn Theatre Presents: Short Attention Span Theatre 2025 Edition

Community Event

Short Attention Span is a collection of short plays to be performed at Red Barn Theatre.

Pertinent and funny short plays with several directors and a big handful of favorite Key West actors, this popular and all new Red Barn show returns to delight audiences.

View Event Page

Start: May 2nd 11:30 PM

Red Barn Theatre

319 Duval Street

Key West

FL

33040

X

Red Barn Theatre Presents: Short Attention Span Theatre 2025 Edition

Community Event

Short Attention Span is a collection of short plays to be performed at Red Barn Theatre.

Pertinent and funny short plays with several directors and a big handful of favorite Key West actors, this popular and all new Red Barn show returns to delight audiences.

View Event Page

Start: May 3rd 11:30 PM

Red Barn Theatre

319 Duval Street

Key West

FL

33040

X

Red Barn Theatre Presents: Short Attention Span Theatre 2025 Edition

Community Event

Short Attention Span is a collection of short plays to be performed at Red Barn Theatre.

Pertinent and funny short plays with several directors and a big handful of favorite Key West actors, this popular and all new Red Barn show returns to delight audiences.

View Event Page

Start: May 22nd 1:00 PM

End: May 23rd 1:00 AM

Sunset Watersports

201 William Street

Key West

FL

33040

X

Sunset Watersports: Memorial Day Weekend Discounted Daily Excursions

Community Event

Marvelous Memorial Day Weekend Specials!

Sunset Watersports is Key West’s Original Watersports Company creating the island's best experiences to provide to our guests. Enjoy snorkeling, parasailing, sunset cruises, jetski tours, dinner cruises, eco adventures & more! Book today to make your Memorial Day weekend memorable.

Sunset Watersports

305-296-2554

View Event Page

Start: May 23rd 1:00 PM

End: May 24th 1:00 AM

Sunset Watersports

201 William Street

Key West

FL

33040

X

Sunset Watersports: Memorial Day Weekend Discounted Daily Excursions

Community Event

Marvelous Memorial Day Weekend Specials!

Sunset Watersports is Key West’s Original Watersports Company creating the island's best experiences to provide to our guests. Enjoy snorkeling, parasailing, sunset cruises, jetski tours, dinner cruises, eco adventures & more! Book today to make your Memorial Day weekend memorable.

Sunset Watersports

305-296-2554

View Event Page

Start: May 24th 1:00 PM

End: May 25th 1:00 AM

Sunset Watersports

201 William Street

Key West

FL

33040

X

Sunset Watersports: Memorial Day Weekend Discounted Daily Excursions

Community Event

Marvelous Memorial Day Weekend Specials!

Sunset Watersports is Key West’s Original Watersports Company creating the island's best experiences to provide to our guests. Enjoy snorkeling, parasailing, sunset cruises, jetski tours, dinner cruises, eco adventures & more! Book today to make your Memorial Day weekend memorable.

Sunset Watersports

305-296-2554

View Event Page

Start: May 25th 1:00 PM

End: May 26th 1:00 AM

Sunset Watersports

201 William Street

Key West

FL

33040

X

Sunset Watersports: Memorial Day Weekend Discounted Daily Excursions

Community Event

Marvelous Memorial Day Weekend Specials!

Sunset Watersports is Key West’s Original Watersports Company creating the island's best experiences to provide to our guests. Enjoy snorkeling, parasailing, sunset cruises, jetski tours, dinner cruises, eco adventures & more! Book today to make your Memorial Day weekend memorable.

Sunset Watersports

305-296-2554

Register for EventView Event Page

Start: May 26th 1:00 PM

End: May 27th 1:00 AM

Sunset Watersports

201 William Street

Key West

FL

33040

X

Sunset Watersports: Memorial Day Weekend Discounted Daily Excursions

Community Event

Marvelous Memorial Day Weekend Specials!

Sunset Watersports is Key West’s Original Watersports Company creating the island's best experiences to provide to our guests. Enjoy snorkeling, parasailing, sunset cruises, jetski tours, dinner cruises, eco adventures & more! Book today to make your Memorial Day weekend memorable.

Sunset Watersports

305-296-2554

Register for EventView Event Page

Start: May 27th 1:00 PM

End: May 28th 1:00 AM

Sunset Watersports

201 William Street

Key West

FL

33040

X

Sunset Watersports: Memorial Day Weekend Discounted Daily Excursions

Community Event

Marvelous Memorial Day Weekend Specials!

Sunset Watersports is Key West’s Original Watersports Company creating the island's best experiences to provide to our guests. Enjoy snorkeling, parasailing, sunset cruises, jetski tours, dinner cruises, eco adventures & more! Book today to make your Memorial Day weekend memorable.

Sunset Watersports

305-296-2554

Register for EventView Event Page

Start: May 8th 1:00 PM

End: May 9th 1:00 AM

Sunset Watersports

201 William Street

Key West

FL

33040

X

Sunset Watersports: Mother's Day Weekend Discounted Daily Excursions

Community Event

Mother's Day activities in Key West with Sunset Watersports!

Explore Key West's breathtaking off-shore waters on thrilling parasail rides, exhilarating jet ski tours, and immersive snorkeling excursions. Set sail on our sunset cruises for a picturesque evening on the water, or discover hidden gems during our sandbar excursions and guided kayak tours.

Enjoy a memorable Mother’s Day on our dolphin eco tours and marvel at these majestic creatures in their natural habitat. With activities suitable for all ages and interests, Sunset Watersports has everything you need to make Mom's holiday unforgettable. Book your adventure today and let the fun begin!

Sunset Watersports

305-296-2554

View Event Page

Start: May 9th 1:00 PM

End: May 10th 1:00 AM

Sunset Watersports

201 William Street

Key West

FL

33040

X

Sunset Watersports: Mother's Day Weekend Discounted Daily Excursions

Community Event

Mother's Day activities in Key West with Sunset Watersports!

Explore Key West's breathtaking off-shore waters on thrilling parasail rides, exhilarating jet ski tours, and immersive snorkeling excursions. Set sail on our sunset cruises for a picturesque evening on the water, or discover hidden gems during our sandbar excursions and guided kayak tours.

Enjoy a memorable Mother’s Day on our dolphin eco tours and marvel at these majestic creatures in their natural habitat. With activities suitable for all ages and interests, Sunset Watersports has everything you need to make Mom's holiday unforgettable. Book your adventure today and let the fun begin!

Sunset Watersports

305-296-2554

View Event Page

Start: May 10th 1:00 PM

End: May 11th 1:00 AM

Sunset Watersports

201 William Street

Key West

FL

33040

X

Sunset Watersports: Mother's Day Weekend Discounted Daily Excursions

Community Event

Mother's Day activities in Key West with Sunset Watersports!

Explore Key West's breathtaking off-shore waters on thrilling parasail rides, exhilarating jet ski tours, and immersive snorkeling excursions. Set sail on our sunset cruises for a picturesque evening on the water, or discover hidden gems during our sandbar excursions and guided kayak tours.

Enjoy a memorable Mother’s Day on our dolphin eco tours and marvel at these majestic creatures in their natural habitat. With activities suitable for all ages and interests, Sunset Watersports has everything you need to make Mom's holiday unforgettable. Book your adventure today and let the fun begin!

Sunset Watersports

305-296-2554

View Event Page

Start: May 11th 1:00 PM

End: May 12th 1:00 AM

Sunset Watersports

201 William Street

Key West

FL

33040

X

Sunset Watersports: Mother's Day Weekend Discounted Daily Excursions

Community Event

Mother's Day activities in Key West with Sunset Watersports!

Explore Key West's breathtaking off-shore waters on thrilling parasail rides, exhilarating jet ski tours, and immersive snorkeling excursions. Set sail on our sunset cruises for a picturesque evening on the water, or discover hidden gems during our sandbar excursions and guided kayak tours.

Enjoy a memorable Mother’s Day on our dolphin eco tours and marvel at these majestic creatures in their natural habitat. With activities suitable for all ages and interests, Sunset Watersports has everything you need to make Mom's holiday unforgettable. Book your adventure today and let the fun begin!

Sunset Watersports

305-296-2554

View Event Page

Start: May 12th 1:00 PM

End: May 13th 1:00 AM

Sunset Watersports

201 William Street

Key West

FL

33040

X

Sunset Watersports: Mother's Day Weekend Discounted Daily Excursions

Community Event

Mother's Day activities in Key West with Sunset Watersports!

Explore Key West's breathtaking off-shore waters on thrilling parasail rides, exhilarating jet ski tours, and immersive snorkeling excursions. Set sail on our sunset cruises for a picturesque evening on the water, or discover hidden gems during our sandbar excursions and guided kayak tours.

Enjoy a memorable Mother’s Day on our dolphin eco tours and marvel at these majestic creatures in their natural habitat. With activities suitable for all ages and interests, Sunset Watersports has everything you need to make Mom's holiday unforgettable. Book your adventure today and let the fun begin!

Sunset Watersports

305-296-2554

View Event Page

Start: May 7th 6:30 PM

X

Reef Relief Virtual Lesson Series: Marine Ecosystems of the Florida Keys

Educational Event

As part of our Marine Science for All Initiative, Reef Relief offers free virtual marine science lessons held via zoom to the public several times each month throughout the school year. These lessons are ideal for homeschool groups and smaller groups, but are open to classrooms and larger groups as well. These lessons are approximately 45 minutes-1 hour live.

View Event Page

Start: May 15th 2:30 PM

X

Reef Relief Virtual Lesson Series: Marine Ecosystems of the Florida Keys

Educational Event

As part of our Marine Science for All Initiative, Reef Relief offers free virtual marine science lessons held via zoom to the public several times each month throughout the school year. These lessons are ideal for homeschool groups and smaller groups, but are open to classrooms and larger groups as well. These lessons are approximately 45 minutes-1 hour live.

View Event Page

Start: May 12th 1:00 AM

Classic Harbor Line - America 2.0

202-R William Street

Key West

FL

33040

X

Classic Harbor Line: Full Moon Sail Aboard Schooner America 2.0

Community Event

Sail through the Key West waters by full moonlight on this romantic Full Moon sailing adventure aboard one of Key West's most stunning modern sailboats, the 105 ft Schooner America 2.0.

This special sail is only offered for a limited time every month! Ticket price includes 1.5 hours of sailing. Drinks and snacks available for purchase.

America 2.0 features teak decks, mahogany-trimmings, and just under 3600 square feet of canvas! Sit back and relax while she sails silently through the evening, basking in the golden moonlight that dances in the night waters.

Some of the sights on this 1.5 hour sailing adventure include:

  • A beautiful Full Moon rising up over Key West
  • Some serious star-gazing opportunities
  • The mystery and excitement of night time sailing in the beautiful surrounding waters of Key West

Bring your family and/or friends and join our courteous and professional crew for this adventurous late night sail that will highlight your Key West experience!

Key Points About This Tour:

  • 1.5-hour Key West moonlight sail on Schooner America 2.0
  • Pricing starts at $68 for adults, $34 for children
  • Adult ticket includes one beer, wine, or champagne
  • Full bar and snacks available for purchase on board (or purchase while booking!)
  • Rated “Top Things to Do” in Key West on Trip Advisor
View Event Page

Start: May 13th 1:00 AM

Classic Harbor Line - America 2.0

202-R William Street

Key West

FL

33040

X

Classic Harbor Line: Full Moon Sail Aboard Schooner America 2.0

Community Event

Sail through the Key West waters by full moonlight on this romantic Full Moon sailing adventure aboard one of Key West's most stunning modern sailboats, the 105 ft Schooner America 2.0.

This special sail is only offered for a limited time every month! Ticket price includes 1.5 hours of sailing. Drinks and snacks available for purchase.

America 2.0 features teak decks, mahogany-trimmings, and just under 3600 square feet of canvas! Sit back and relax while she sails silently through the evening, basking in the golden moonlight that dances in the night waters.

Some of the sights on this 1.5 hour sailing adventure include:

  • A beautiful Full Moon rising up over Key West
  • Some serious star-gazing opportunities
  • The mystery and excitement of night time sailing in the beautiful surrounding waters of Key West

Bring your family and/or friends and join our courteous and professional crew for this adventurous late night sail that will highlight your Key West experience!

Key Points About This Tour:

  • 1.5-hour Key West moonlight sail on Schooner America 2.0
  • Pricing starts at $68 for adults, $34 for children
  • Adult ticket includes one beer, wine, or champagne
  • Full bar and snacks available for purchase on board (or purchase while booking!)
  • Rated “Top Things to Do” in Key West on Trip Advisor
View Event Page

Start: May 17th 11:00 PM

End: May 18th 3:00 AM

Beachside Resort & Residences

3841 N Roosevelt Boulevard

Key West

FL

33040

X

9th Annual Rotary Club of Key West: Glow Big or Go Home Casino Night

Annual Event

SAVE THE DATE!

9th Annual Rotary Club of Key West Casino Night hosted by Beachside Resort & Residences

 

 

View Event Page

Start: May 2nd 12:00 AM

Coffee Butler Amphitheater

21 East Quay Road

Key West

FL

33040

X

Rams Head Presents: Nate Smith with Chase Matthew

Community Event

Featuring a mix of gritty backwoods soul, rock ‘n’ roll swagger and velvet-thunder vocals, Nate Smith is Sony Music Nashville’s latest signing whose personal journey inspired him to be a beacon of country-music hope, an inspirational mission he puts front-and-center. A California native, former worship leader, and lifelong music lover, Smith approaches that mission with a background as eclectic as it gets. Learning guitar at 13, Garth Brooks, Elvis Presley and Bob Seger were among those informing his powerful, fire-from-within vocals, while Michael Jackson made him crave the spotlight and Nirvana gave his sound a jagged edge. He first chased his neon dreams to Nashville in his early 20s – but it didn’t stick. The disheartened Smith returned home and thought he was “100-percent done” with his artistic journey…until a crucible of change burned away the past.

In 2018, Smith lost everything he owned in the devastating Camp Fire which tore through Paradise, California, now known as the deadliest and most destructive wildfire in the state’s history. Although his family was safe, he struggled to cope and turned back to music, hoping that it would help comfort himself and others. Help it did, inspiring a month-long road trip across the U.S. to Music City, writing music and playing dive bars along the way. Soon after his arrival to Nashville, Nate released his biggest song to date, “Wildfire,” and landed a publishing deal with Sony ATV. Since then, he’s released new music including “Sleeve” and “Under My Skin,” which has amassed over 45 million on-demand streams to date. The singer was named a Spotify Hot Country Artist to Watch for 2021 – an accurate prediction as he rounded out the year with a record deal and two brand new songs: “Raised Up” and the viral TikTok hit “I Don’t Wanna Go To Heaven.” Nate is managed by Kevin “Chief” Zaruk and Simon Tikhman with The Core Entertainment.

View Event Page

Start: May 15th 10:00 PM

End: May 16th 1:00 AM

Various Shops and Studios

White Street

X

Walk on White

Community Event

Fancy a Thursday evening art stroll along historic White Street? Join us for Walk On White on the third Thursday of every month!

  • Thursday, May 15, 2025
  • 6:00?PM  9:00?PM

 

Join us for Walk on White on the third Thursday of every month! Open this event to see special events and features this month.

In May, there will be a bike parade down White Street for American Bike Month. KW Mile Markers will also be at Zintsmaster & Team.


The 2024-2025 season is presented by Coldwell Banker Schmitt Real Estate and Zintsmaster & Team.

 

Walk On White begins at the Historic Armory at 600 White Street, corner of Southard Street, and makes its way down to United Street. Along this half-mile stretch you’ll find well-known galleries, discover artists’ studios, explore specialty stores & there are many global eateries to graze at along the way.

 

From its early beginnings in 1998, as an annual ‘Holiday Walk On White’, it soon evolved into a monthly event to promote local galleries & celebrate the arts. Walk On White helped establish this area of Key West as the ‘White Street Arts District’.

 

Be sure to visit all these fine galleries and studios:

The Studios at the Armory
Erika Heffernan
Native Materials
Stone Soup Gallery
Coffee Mill Dance Studio
Harrison Gallery
Shade Ceramics and Shutter Photography
B.I.G. - Bone Island Graphics
Gallery 1:11 (1012 Truman Ave)

 

Many fine businesses along White Street also participate in Walk on White.

 

The Armory at 600 White St is home to artist studios on the 2nd floor & has a large performance & gallery space that houses The Fringe Theater in its main hall downstairs. It’s on the National Register of Historic Places & was the birth place of The Studios of Key West.

 

While you are gallery hopping, look out for these impressive & historic landmarks. Please be respectful of noise outside private homes.

Military Burial Grounds, 600 block of White St, 19th century hallowed site

Elizabeth Bishop Home, 624 White St (private residence)

John ‘Pappa Jack’ Willlams c1880, 820 White St, now the Palms Hotel

The Cold’s Milk Farm c1850, 823 White St (private residence), Oldest house on White St

Giant Kapok trees, Harvey Gov. Center, Cnr White & Truman Ave

 

After feeding your soul with everything ART you’ll find a handful of niche, international eateries to feed your belly.

Pierogi Market Place, 1008 White St, Polish

Key West Cakes, 1014 White St (closes 7pm)

Oasis, 1019 White St, Mediterranean

Mayanjali, 1114 White St, Organic cafe

Sandy’s Cafe, 1026 White St, Cuban

Fausto’s, 1105 White St (closes 8pm)

Mo’s, 1116 White St, Creole

The Local Butcher & Market, 1202 White St, Boutique butcher shop and market

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Start: May 5th 12:00 PM

End: May 9th 12:00 PM

Havana, Cuba

X

The Studios of Key West: Havana Art Tour

Community Event

For over a decade, The Studios has led pioneering cultural exchanges with Cuba, building friendships with many of its most significant artists and cultural figures. Reap the benefits of those relationships with a whirlwind tour of Havana’s arts scene, including studio visits with celebrated artists, guided tours and sumptuous dinners, as well as opportunities to learn about the historic and architectural treasures of one of the world’s most romantic cities – a UNESCO World Heritage site!

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Start: May 9th 9:00 PM

End: May 10th 12:30 AM

Lagerheads Beach Bar

0 Simonton Street

Key West

FL

33040

X

Reef Relief Annual Luau

Annual Event

Family Friendly event! Music by Gary Hempse, limbo competition, jeopardy game, sand castle building contest, educational activities by Reef Relief, a nose to toes raffle, and a silent auction. 

View Event Page

Start: May 9th 9:00 PM

End: May 10th 1:30 AM

Fort East Martello Museum

3501 S Roosevelt Boulevard

Key West

FL

33040

X

Free Key West Outdoor Movie Night!

Community Event

Join us for the season finale on May 9th at Fort East Martello for a free outdoor movie night!  Enjoy delicious food from our vendors, including fresh-squeezed lemonade, frozen treats, and all your favorite snacks. Plus, don’t forget the free popcorn, courtesy of First State Bank of the Florida Keys which benefits the Key West High School!  Don’t miss out on this wonderful community event. We can’t wait to see you there! #MovieNight #CommunityEvent #keywestoutdoormovies

Invite your friends, bring your blankets and chairs, and let's make this outdoor movie night one for the books! Don't forget to share this post and spread the word. It's going to be a blockbuster season, and we can't wait to see you there!

Time: Dusk
Location: The Parade Grounds at Fort East Martello.
3501 S Roosevelt Blvd, Key West, FL 33040

There will be food and drink vendors, FREE popcorn, activities and MORE!

The Parade Grounds will open at 5:00 Pm. The Vendors will be there ready for hungry movie-goers! Feel free to come by, grab some food and pick a good spot!
Movie Time: Dusk

View Event Page

Start: Apr 17th 12:00 AM

End: May 3rd 4:00 AM

Waterfront Playhouse

407 Wall Street

Key West

FL

33040

X

Waterfront Playhouse: Wait Until Dark

Community Event

The final show of the season is, according to the New York Post, “A first rate shocker… The suspense drama we’ve long awaited eagerly… A classic”. Written in 1966 by Frederick Knott and then adapted by Jeffrey Hatcher in 2013, this is the story of a blind woman in Greenwich Village in post WWII America imperiled by con men who are trying to recover diamonds that have accidentally come into her possession.  It is “Wait Until Dark” April 16th to May 3rd.

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Start: May 9th 11:00 PM

Key West Theater

512 Eaton Street

Key West

FL

33040

X

Rams Head Presents: Paula Poundstone

Community Event

Iconic comedian Paula Poundstone is known for her smart, observational humor and a spontaneous wit that has become the stuff of legend. She regularly plays theaters across the country, hosts a weekly comedy podcast, Nobody Listens to Paula Poundstone, and is a regular panelist on NPR’s Wait, Wait… Don’t Tell Me. Paula has starred in several HBO specials, including Cats, Cops and Stuff, which nabbed a cable ACE award for Best Comedy Special. She was the first female comic to host the White House Correspondents Dinner. She filed live coverage of the 1992 Democratic and Republican National Conventions and the Presidential Inaugural for The Tonight Show with Jay Leno and at the 93rd Emmy Awards. Paula has starred in two television series, both entitled The Paula Poundstone Show. Paula’s second book, The Totally Unscientific Study of the Search for Human Happiness, was one of eight semi-finalists for the Thurber Prize For American Humor; the audiobook was one of five finalists for the AUDIE award for Audiobook of the Year. Paula has released five albums and is featured in several documentaries and compendiums noting influential comedians of our time.

Venue Information:
Key West Theater
512 Eaton St
Key West, FL, 33040

View Event Page

Start: May 15th 11:00 PM

Key West Theater

512 Eaton Street

Key West

FL

33040

X

Rams Head Presents: Duane Betts & Palmetto Motel

Community Event

Duane Betts ignites and brings an evolution to the Southern rock tradition. With a fiery legacy forged by his father, the legendary Dickey Betts, the second generation musician infuses it with his own soul-stirring blend of blues, raw passion, and six-string mastery. Backed by his band, Palmetto Motel, Betts delivers a dynamic live show filled with searing guitar solos, heartfelt storytelling, and a mix of classic influences with fresh energy. Fans can expect a blend of roots rock, blues, and some improvisational jamming, creating an electrifying yet deeply authentic experience. With top-tier musicianship, a connection to rock ‘n’ roll history, and the desire to make every performance a true experience, a Palmetto Motel show is an unforgettable journey that no music lover should miss.

Palmetto Motel is…
Johnny Stachela (guitar, vocals)
Pedro Arevalo (bass, vocals)
Vincent Fossett Jr. (drums)
Max Butler (B-3 organ)

Venue Information:
Key West Theater
512 Eaton St
Key West, FL, 33040

View Event Page

Start: May 20th 11:00 PM

Key West Theater

512 Eaton Street

Key West

FL

33040

X

Rams Head Presents: Journeyman: Tribute to Eric Clapton

Community Event

JOURNEYMAN – The ONLY nationally touring tribute to ERIC CLAPTON! Fronted by Shaun Hague (Kenny Wayne Shepherd, Amos Lee, John Waite), JOURNEYMAN has become the #1 tribute to Clapton in a very short amount of time. The band has been selling hundreds of tickets per night in the Midwest, New England and West Coast. With over 50 years of music to choose from, JOURNEYMAN covers it all – “Layla”, “Badge”, “The Core”, “White Room”, “Lay Down Sally”, “Tulsa Time”, “Cocaine” and many more. “This gifted group of musicians channel the spirit, passion and musicianship of Clapton himself. The guitar playing is spot on recreating the Clapton catalog in all its splendid glory”- Patrick Norton / Talent Buyer @ Narrows Center for the Arts – Fall River, MA “The best Eric Clapton tribute that we have ever worked with.”- Adam Spriggs / Talent Buyer @ Saint Rocke – Hermosa Beach, CA

Venue Information:
Key West Theater
512 Eaton St
Key West, FL, 33040

View Event Page

Start: May 11th 2:00 PM

End: May 11th 7:00 PM

Pier House Resort & Caribbean Spa

1 Duval Street

Key West

FL

33040

X

Seaside Mother’s Day Brunch at One Duval in Key West’s Pier House Resort & Spa

Community Event

This Mother’s Day, Pier House Resort & Spa is offering a way to treat the most important women to an unforgettable culinary experience at One Duval, the signature oceanfront restaurant at Pier House Resort & Spa in Key West. On Sunday, May 11th, from 10 am to 3 pm, One Duval will host an indulgent Mother’s Day Brunch featuring chef-curated stations, coastal elegance, and bottomless mimosas—all set against breathtaking views of the Gulf.

 

Guests will enjoy a lavish multi-station spread including:

Chilled Seafood Station & Raw Bar with fresh ocean delights

Carving Station featuring Green Tea Crusted Ahi Tuna and Rosemary Crusted Prime Rib

Entree Highlights like Lobster Ravioli with brandy cream sauce and Guava-Glazed Airline Chicken Breast

Decadent Desserts including Crème Brûlée Filled Donuts, Key Lime Pie, and Dulce De Leche Cheesecake

 

With made-to-order omelets, artisan cheeses, seasonal salads, and a variety of elevated sides like truffle mash and bacon mac & cheese, this brunch promises to satisfy every palate.


Adults – $90 with bottomless mimosas
Children 12 and under – $35

 

Reservations are recommended and can be made by visiting Open Table. 

View Event Page

Start: May 2nd 10:00 PM

End: May 3rd 1:00 AM

500 Block of Fleming Street to Grinnell Street

Key West

FL

33040

X

First Fridays on Fleming

Community Event

Celebrate with local business owners for First Fridays on Fleming - a monthly 'shop local' evening stroll along historic Fleming St in Key West.

Vibrant boutiques, galleries, antique stores, artist studios, restaurants, a cocktail lounge, bookstore, yoga sanctuary & other creative businesses open their doors from 6-9pm on the 1st Friday of every month. From the 500 block all the way to Grinnell St.

Enjoy exhibition openings, jewelry trunk shows, book signings, plein-air painting, libations and tastings, live music, special offerings + seasonal events.

First Fridays on Fleming include the Fab 500 Block, home to a dozen locally-owned businesses and the original First Fridays.

More than a dozen businesses open their doors from 6-9pm every First Friday. Join us every month and show your love of local.

From all of us on Fleming Street, we look forward to seeing you!

View Event Page

Start: May 15th 11:00 PM

Schooner Wharf Bar at KW Seaport

202-R William Street

Key West

FL

33040

X

28 Years of Close Up Magic at Schooner Wharf Bar

Community Event

Monday May 15th, Schooner Wharf celebrates 28 years of their very own Comedy Magic Bar featuring Frank Everhart! Frank will be on hand, with friends from far and near, along with a collection of special guests armed with Magic, Stories, and Songs to commemorate a quarter century of legendary Magical entertainment!

Master of ceremonies Bill Hoebee, Iheartradio.com, will kick off the evening with an introduction. This is just in case we have a few who really do not know what's going on!

Live performances will follow with Music at 7pm with The Newton's Toko Irie, playing current and classic favorites with the steel band sound of the islands.. Sway the night away to reggae!

Toko Irie will continue the musical excitement for the dance floor crowd as Frank and visiting Magicians make for the Magic bar for a historical night with a lot of tricks and no sleeves to put them up!

The audience will be treated to late-night special appearance from world renowned stage Magic sensation, magician and illusionist Nicholas Tweedy!

Be prepared to be amazed.

It's all happening live Sunday, May 15th at the Schooner Wharf Bar, now home of the current longest running Magic Bar in, not one but two countries, America & The Conch Republic! For more information go to schoonerwharf.com or call (305) 292-9520.

View Event Page

Start: May 1st 2:00 PM

End: May 1st 3:15 PM

Key West Botanical Garden Society

5210 College Road

Key West

FL

33040

X

Prime of Life Yoga at the Key West Tropical Forest & Botanical Gardens

Community Event

All Prime of Life Yoga® classes are small and ideal for exploring yoga for the first time or getting back into your practice and benefiting from individual attention.

SUMMER SESSION NOTES:

Our summer classes are in the beautiful — and air conditioned — Nature Chapel!

Summer classes may not always be right on schedule, so it might be a good idea to text or call 305-304-5635 or email yogakeywest@gmail.com

 
Tuesdays, Thursdays, Saturdays

10 a.m. — 11:15 a.m.

10 classes for $150

20 classes for $250

Garden Members receive one additional free class with purchase of a 10- or 20-class package

The drop-in rate is $20

 

A part of all class fees go to support the conservation work of KWBGS.

Other than for our summer season, yoga classes meet outdoors on the Lakeside Terrace when the weather is good, which is most of the time.

If it is raining or too hot or cold, we meet in the Nature Chapel. Usually, Monica leads the Tuesday / Thursday / Saturday yoga classes.

Purchasing a yoga class  includes FREE admission to the Garden for the entire day

View Event Page

Start: May 3rd 2:00 PM

End: May 3rd 3:15 PM

Key West Botanical Garden Society

5210 College Road

Key West

FL

33040

X

Prime of Life Yoga at the Key West Tropical Forest & Botanical Gardens

Community Event

All Prime of Life Yoga® classes are small and ideal for exploring yoga for the first time or getting back into your practice and benefiting from individual attention.

SUMMER SESSION NOTES:

Our summer classes are in the beautiful — and air conditioned — Nature Chapel!

Summer classes may not always be right on schedule, so it might be a good idea to text or call 305-304-5635 or email yogakeywest@gmail.com

 
Tuesdays, Thursdays, Saturdays

10 a.m. — 11:15 a.m.

10 classes for $150

20 classes for $250

Garden Members receive one additional free class with purchase of a 10- or 20-class package

The drop-in rate is $20

 

A part of all class fees go to support the conservation work of KWBGS.

Other than for our summer season, yoga classes meet outdoors on the Lakeside Terrace when the weather is good, which is most of the time.

If it is raining or too hot or cold, we meet in the Nature Chapel. Usually, Monica leads the Tuesday / Thursday / Saturday yoga classes.

Purchasing a yoga class  includes FREE admission to the Garden for the entire day

View Event Page

Start: May 6th 2:00 PM

End: May 6th 3:00 PM

Key West Botanical Garden Society

5210 College Road

Key West

FL

33040

X

Story Time at the Key West Tropical Forest & Botanical Gardens

Educational Event

We host Story Time for our Seedling Scientists weekly. This program is perfect for Toddler through Pre-K and features stories, crafts, and activities.

Toddler through Pre-K

Stories, activities and crafts

Tuesdays, 10 a.m.-11 a.m.

 In the Garden

Free or a donation

View Event Page

Start: May 13th 2:00 PM

End: May 13th 3:00 PM

Key West Botanical Garden Society

5210 College Road

Key West

FL

33040

X

Story Time at the Key West Tropical Forest & Botanical Gardens

Educational Event

We host Story Time for our Seedling Scientists weekly. This program is perfect for Toddler through Pre-K and features stories, crafts, and activities.

Toddler through Pre-K

Stories, activities and crafts

Tuesdays, 10 a.m.-11 a.m.

 In the Garden

Free or a donation

View Event Page

Start: May 20th 2:00 PM

End: May 20th 3:00 PM

Key West Botanical Garden Society

5210 College Road

Key West

FL

33040

X

Story Time at the Key West Tropical Forest & Botanical Gardens

Educational Event

We host Story Time for our Seedling Scientists weekly. This program is perfect for Toddler through Pre-K and features stories, crafts, and activities.

Toddler through Pre-K

Stories, activities and crafts

Tuesdays, 10 a.m.-11 a.m.

 In the Garden

Free or a donation

View Event Page

Start: May 27th 2:00 PM

End: May 27th 3:00 PM

Key West Botanical Garden Society

5210 College Road

Key West

FL

33040

X

Story Time at the Key West Tropical Forest & Botanical Gardens

Educational Event

We host Story Time for our Seedling Scientists weekly. This program is perfect for Toddler through Pre-K and features stories, crafts, and activities.

Toddler through Pre-K

Stories, activities and crafts

Tuesdays, 10 a.m.-11 a.m.

 In the Garden

Free or a donation

Register for EventView Event Page

Start: May 17th 1:00 PM

End: May 17th 4:00 PM

Key West Botanical Garden Society

5210 College Road

Key West

FL

33040

X

Native Plant Sale at the Key West Tropical Forest & Botanical Garden

Community Event

Native Plant Sale!

Ready to take your island garden to a new level? Start with our experts in the Garden’s Native Plant Nursery. Every third Saturday we are here to help you choose the right native plants and trees for our Zone 11 gardens.

 

Master Gardeners will be on site to answer any plant questions.  The Nursery has 160 species of native trees, shrubs & vines available including Native & Cuban palms, and vegetable plants.  There are more than 2,000 plants which attract birds, butterflies and other pollinators in 1-gallon to 15-gallon pots.  Key West Botanical Garden members receive a 15% discount.  Memberships are available on site.  The Garden is a 501 (c) 3 non-profit corporation and all proceeds directly benefit the Garden’s conservation program.  

Our Garden Guardians cultivate hundreds of Florida Keys native plants and trees designed to flourish in our Zone 11 sub-tropical climate. Not only are they beautiful specimens, but our native plants are salt and drought tolerant, require minimal care and will work for every type of island landscaping.

The Nursery has 160 species of native plants available including Native & Cuban palms, Tomato and Pepper plants.  The total nursery inventory totals more than 2,000 plants which attract birds, butterflies and other pollinators in 1-gallon to 15-gallon pots.  Key West Botanical Garden members receive a 15% discount.  Memberships are available on site.  The Garden is a 501 (c) 3 non-profit corporation and all proceeds directly benefit the Garden’s conservation program.

On the third Saturday of each month, our experts are on hand to help you choose the right combination to take your tropical garden to the next levels. We will assist with selection, help you understand the care needed and guide you each step of the way.

WHEN: 9 a.m.-Noon, third Saturday of each month.

VOLUNTEER: We welcome Garden Guardian volunteers willing to work with us each Wednesday and Saturday. You can register here: https://www.keywest.garden/become-a-volunteer/

View Event Page

Start: May 2nd 10:00 PM

End: May 2nd 11:00 PM

Key West Yoga Sanctuary

612 Fleming St.

Key West

FL

33040

X

Key West Yoga Sanctuary: FREE Community Yoga Class/Donation Based

Community Event

Service, Seva in Sanskrit, is an integral part of yoga.  There is an entire yogic tradition, Karma Yoga, entirely devoted to selfless service.  At the Key West Yoga Sanctuary we are committed to serving the local community and supporting our global community.

One of the ways that we fulfill this commitment is by offering regular, free community classes.   These classes are listed on our regular schedule as COMMUNITY CLASS, they are open to the community at large and are completely free of charge.   If it feels appropriate and is within your means to make a donation towards these classes, you are welcome to; any proceeds will be granted to the non-profit organization Yoga Gives Back (yogagivesback.org).

The benefits of yoga are universal and we want to share these benefits with under-resourced populations beyond our premises on Fleming Street.  If you have a local group or organization that is interested in yoga, perhaps we can be of service to you. Email us to start a conversation on Yoga outreach.  Together we can spread the Love.

View Event Page

Start: May 15th 4:00 PM

End: May 15th 5:00 PM

Via Zoom Link

X

SBDC at FIU: Government Contracting 101 Webinar

Educational Event

SBDC at FIU Business Webinars

Government Contracting 101 Webinar 

May 15, 2025

12PM - 1PM

Via Zoom

Register: go.fiu.edu/apex

View Event Page

Start: May 16th 4:00 PM

End: May 16th 5:00 PM

Via Zoom Link

X

SBDC at FIU: Finding and Winning Federal Contracts

Educational Event

SBDC at FIU Business Webinars:

Finding and Winning Federal Contarcts

May 16, 2025

12PM - 1PM

Via Zoom 

Register at go.fiu.edu/apex

View Event Page

Start: May 1st 12:00 PM

End: May 4th 12:00 PM

See Schedule on Website

X

3rd Annual I.Care Trash Derby

Annual Event

I.CARE's Trash Derby sponsored by the National Marine Sanctuary Foundation in support of Goal: Clean Seas will include two days of debris collection sunrise to sunset from Key Largo to Key West. Check out how you can participate and help us "Triumph Over Trash".

I.CARE’s Trash Derby, sponsored by the National Marine Sanctuary Foundation in support of Goal: Clean Seas, brings teams of environmentally-conscious debris collectors in divisions including dive charters, private boat owners and land lovers. After two days of trash collecting, there is a free festival Sunday at Founders Park, mile marker 87 bayside from noon to 6 p.m. The festival is open to the public. There is to be an awards ceremony to include cash and other special prizes. The festival features live music, food vendors, games and activities, raffles, a silent auction and exhibitors including local organizations helping to restore Keys coral reefs.

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Start: May 11th 5:00 PM

End: May 11th 7:00 PM

Monroe County Sheriff's Office Animal Farm

5501 College Road

Key West

FL

33040

X

Monroe County Sheriff's Office Animal Farm Open House

Community Event

Looking for a fun place to take the kids? The Monroe County Sheriff's Office Animal Farm is open to the public on the second and fourth Sunday of each month from 1 to 3 p.m. Come visit the animals at the farm including miniature horses, a steer, pigs, goats, bunnies, alligators, tropical birds, kinkajous, a lemur, an alpaca, a skunk, a prairie dog, tortoises and turtles, snakes, and many more. It's FREE, but donations are always appreciated to help maintain the farm.

View Event Page

Start: May 17th 12:00 PM

End: May 18th 12:00 PM

Key Largo to Key West (see organizer's website)

X

The 17th Annual Keys100 Ultramarathon

Annual Event

Registration is open for the 17th Annual race across the islands of the Florida Keys--May 17-18, 2025.  This chain of unique and inter-connected islands--some inhabited, some not--end in the City of Key West, just 90 miles from Cuba. This is a pavement race, with approximately 75% run off-road and the balance on the road shoulder facing traffic.  The Florida Keys, known locally as "The Conch Republic", is a spectacular and laid-back sub-tropical paradise, surrounded by the turquoise waters of the Atlantic Ocean and Florida Bay/Gulf of Mexico. The Keys feature great fishing, kayaking, snorkeling and diving, hotels, resorts, B&B's and cuisine and cocktails to fit every budget. There is entertainment to fit every taste, important history and a unique culture, sunsets that will keep you spellbound, special events going on throughout the year including KEYS100, of course, and you don't need a passport to visit here! So, what are you waiting for? We've saved a space for you!

View Event Page

Start: May 6th 2:00 PM

End: May 6th 3:30 PM

Via Zoom

X

Tourist Development Council: State of the Tourism Industry Meeting Update

Community Event

Visit Florida Keys will celebrate National Travel & Tourism Week with a special "State of the Tourism Industry" presentation of new visitor profile research and tourism data on Tuesday, May 6 at 10 a.m via Zoom. President and CEO Kara Franker will be joined by TDC staff to present the latest numbers and tourism insights. The presentation length will be approximately 90 minutes.

Please stay tuned for more details and meeting links.

View Event Page

Start: May 29th 2:00 PM

End: May 29th 3:30 PM

Via Zoom

X

Tourist Development Council: Hurricane Preparedness Workshop

Community Event

On Thursday, May 29 at 10 a.m. we will present the annual Hurricane Preparedness Workshop via Zoom with brief presentations from emergency management and weather experts to help you prepare both your business and home for the upcoming storm season. The workshop length will be approximately 90 minutes.

Please stay tuned for more details and meeting links.

View Event Page

Start: May 9th 12:00 PM

End: May 10th 12:00 PM

Higgs Beach

1000 Atlantic Blvd

Key West

FL

33040

X

The 28th Annual Key West Paddle Classic 2025

Annual Event

Join Florida Keys Watermans Company as we celebrate taking over as hosts of the Key West Paddle Classic!  The event has a long history, originating in 1997 under the direction of Micheal O'Shaunessy, and is celebrating its 28th year in 2025! Lazy Dogs hosted the event from 2013-2024 and graciously passed the torch to us for this year!   

If you have been a regular and racing the event for years, we thank you for coming back!  If it is on your race ‘bucket’ list, well my friends, THIS IS YOUR YEAR!  

Registration is now open via PaddleGuru. Expect nothing different!  An affordable race, a challenging course, and great stories of our paddle experience together on the water!

 

Paddle Around Key West - 12 Mile open water 

Starting point is at Higgs Beach, Paddle South toward the Southernmost Point, through the Key West harbor, around the USCG base and under the Fleming Key Bridge. From here we cross the sailboat mooring field and paddle around Dredger's Key (Sigsbee) into Cow Key Channel which connects Key West and Stock Island.  Exit Cow Key Channel back out at the front side and continue past Smather's Beach and White St. Pier to return to Higgs Beach for the finish.

RELAY TEAMS ONLY

View Event Page

Start: May 1st 6:00 PM

End: May 1st 11:00 PM

Truman Waterfront Park

End of Southard Street

Key West

FL

33040

X

Truman Waterfront Farmers Market

Community Event

Join us every Thursday from 2-7 p.m. for the Truman Waterfront Farmers Market. With a variety of vendors and things to do, it's fun for everyone!

 

When is the Farmer’s Market? Every Thursday, 2 p.m. to 7p.m., rain or shine (too much rain and they pack it up, though). The Market will continue as long as there is strong community support.

 

Who should go? The Key West Farmer’s Market is for locals and visitors alike. Residents will find quality items to stock the fridge and pantry, gifts and home décor while sampling fun new lunch choices. Vacationers will love shopping with a view, reasonable food options and plenty to see and do at the Park.

 

Where is the Farmer’s Market exactly? At the Truman Waterfront, end of Southard Street. Look for tents on the Quay by the USCG Ingham on the waterfront.

 

What does it cost? Entrance into the Park and Market is always free. Some vendors do not take credit cards. The closest ATM is at the Green Parrot.

 

Where is parking? There is a large City lot directly adjacent to the market with plenty of parking, handicapped spots, and bicycle racks.

 

What does parking cost? The City lot has pay stations that take credit card or cash. Rates are $4/hour or free for up to 4 hours with a Resident sticker. Handicapped spots are always free and are monitored.

 

Can I ride a bus? The Duval Loop conveniently stops at the round-about on the half hour. Download their app or check here for info.

 

What kind of vendors? Every week you’ll find traditional farmer’s market fare including produce, seasonal fruits, cheese, pickles, nuts, honey, seafood, fresh breads, hot sauces, and more. There are food stands and food trucks. Artists, crafters, flea market goods, jewelry, clothing/t-shirts, local organizations – cigars and CBD – it’s an eclectic group of small businesses who collectively offer one-stop shopping at our weekly pop-up island bazar.

 

What else is there to do at the park? The USCG Ingham is a self-guided maritime museum open Tuesday – Saturday 10 a.m. to 4 p.m. $10 adults/$5 kids/$5 active military. Truman Waterfront park features a splash park, playground, and lots of grass to spread out a picnic. Restrooms & shower rinse. The Quay faces the Gulf and often cruise ships and Navy cutters on duty will be parked nearby. There are plenty of park benches to enjoy the view (but little shade, umbrella recommended), Fort Zachary Taylor Beach & State Park is a National Historic Landmark on 54 acres and houses a civil war fortress and the best beach on Key West. Entrance fees start at $2.50 and up.

 

What kind of food options? There’s a little bit of everything week to week which may include Poke Bowls, Indian, Mediterranean, fresh fish and seafood, smoothies, bread and French pastries, and brewed coffees. Come for a late lunch or picnic for dinner.

 

Can I bring my pet? Well behaved pets are welcome. Please be sure to bring water and bags.

 

Where are restrooms? Restrooms are located within the splash park/playground area. There’s also a water fountain.

 

Can we have a picnic? By all means, grab some lunch from one of the vendors and find a shady spot. You may want to bring a blanket or lawn chair and an umbrella for the summer sun. The entire park and Market area, restrooms, and parking lots are wheelchair accessible.

View Event Page

Start: May 8th 6:00 PM

End: May 8th 11:00 PM

Truman Waterfront Park

End of Southard Street

Key West

FL

33040

X

Truman Waterfront Farmers Market

Community Event

Join us every Thursday from 2-7 p.m. for the Truman Waterfront Farmers Market. With a variety of vendors and things to do, it's fun for everyone!

 

When is the Farmer’s Market? Every Thursday, 2 p.m. to 7p.m., rain or shine (too much rain and they pack it up, though). The Market will continue as long as there is strong community support.

 

Who should go? The Key West Farmer’s Market is for locals and visitors alike. Residents will find quality items to stock the fridge and pantry, gifts and home décor while sampling fun new lunch choices. Vacationers will love shopping with a view, reasonable food options and plenty to see and do at the Park.

 

Where is the Farmer’s Market exactly? At the Truman Waterfront, end of Southard Street. Look for tents on the Quay by the USCG Ingham on the waterfront.

 

What does it cost? Entrance into the Park and Market is always free. Some vendors do not take credit cards. The closest ATM is at the Green Parrot.

 

Where is parking? There is a large City lot directly adjacent to the market with plenty of parking, handicapped spots, and bicycle racks.

 

What does parking cost? The City lot has pay stations that take credit card or cash. Rates are $4/hour or free for up to 4 hours with a Resident sticker. Handicapped spots are always free and are monitored.

 

Can I ride a bus? The Duval Loop conveniently stops at the round-about on the half hour. Download their app or check here for info.

 

What kind of vendors? Every week you’ll find traditional farmer’s market fare including produce, seasonal fruits, cheese, pickles, nuts, honey, seafood, fresh breads, hot sauces, and more. There are food stands and food trucks. Artists, crafters, flea market goods, jewelry, clothing/t-shirts, local organizations – cigars and CBD – it’s an eclectic group of small businesses who collectively offer one-stop shopping at our weekly pop-up island bazar.

 

What else is there to do at the park? The USCG Ingham is a self-guided maritime museum open Tuesday – Saturday 10 a.m. to 4 p.m. $10 adults/$5 kids/$5 active military. Truman Waterfront park features a splash park, playground, and lots of grass to spread out a picnic. Restrooms & shower rinse. The Quay faces the Gulf and often cruise ships and Navy cutters on duty will be parked nearby. There are plenty of park benches to enjoy the view (but little shade, umbrella recommended), Fort Zachary Taylor Beach & State Park is a National Historic Landmark on 54 acres and houses a civil war fortress and the best beach on Key West. Entrance fees start at $2.50 and up.

 

What kind of food options? There’s a little bit of everything week to week which may include Poke Bowls, Indian, Mediterranean, fresh fish and seafood, smoothies, bread and French pastries, and brewed coffees. Come for a late lunch or picnic for dinner.

 

Can I bring my pet? Well behaved pets are welcome. Please be sure to bring water and bags.

 

Where are restrooms? Restrooms are located within the splash park/playground area. There’s also a water fountain.

 

Can we have a picnic? By all means, grab some lunch from one of the vendors and find a shady spot. You may want to bring a blanket or lawn chair and an umbrella for the summer sun. The entire park and Market area, restrooms, and parking lots are wheelchair accessible.

View Event Page

Start: May 15th 6:00 PM

End: May 15th 11:00 PM

Truman Waterfront Park

End of Southard Street

Key West

FL

33040

X

Truman Waterfront Farmers Market

Community Event

Join us every Thursday from 2-7 p.m. for the Truman Waterfront Farmers Market. With a variety of vendors and things to do, it's fun for everyone!

 

When is the Farmer’s Market? Every Thursday, 2 p.m. to 7p.m., rain or shine (too much rain and they pack it up, though). The Market will continue as long as there is strong community support.

 

Who should go? The Key West Farmer’s Market is for locals and visitors alike. Residents will find quality items to stock the fridge and pantry, gifts and home décor while sampling fun new lunch choices. Vacationers will love shopping with a view, reasonable food options and plenty to see and do at the Park.

 

Where is the Farmer’s Market exactly? At the Truman Waterfront, end of Southard Street. Look for tents on the Quay by the USCG Ingham on the waterfront.

 

What does it cost? Entrance into the Park and Market is always free. Some vendors do not take credit cards. The closest ATM is at the Green Parrot.

 

Where is parking? There is a large City lot directly adjacent to the market with plenty of parking, handicapped spots, and bicycle racks.

 

What does parking cost? The City lot has pay stations that take credit card or cash. Rates are $4/hour or free for up to 4 hours with a Resident sticker. Handicapped spots are always free and are monitored.

 

Can I ride a bus? The Duval Loop conveniently stops at the round-about on the half hour. Download their app or check here for info.

 

What kind of vendors? Every week you’ll find traditional farmer’s market fare including produce, seasonal fruits, cheese, pickles, nuts, honey, seafood, fresh breads, hot sauces, and more. There are food stands and food trucks. Artists, crafters, flea market goods, jewelry, clothing/t-shirts, local organizations – cigars and CBD – it’s an eclectic group of small businesses who collectively offer one-stop shopping at our weekly pop-up island bazar.

 

What else is there to do at the park? The USCG Ingham is a self-guided maritime museum open Tuesday – Saturday 10 a.m. to 4 p.m. $10 adults/$5 kids/$5 active military. Truman Waterfront park features a splash park, playground, and lots of grass to spread out a picnic. Restrooms & shower rinse. The Quay faces the Gulf and often cruise ships and Navy cutters on duty will be parked nearby. There are plenty of park benches to enjoy the view (but little shade, umbrella recommended), Fort Zachary Taylor Beach & State Park is a National Historic Landmark on 54 acres and houses a civil war fortress and the best beach on Key West. Entrance fees start at $2.50 and up.

 

What kind of food options? There’s a little bit of everything week to week which may include Poke Bowls, Indian, Mediterranean, fresh fish and seafood, smoothies, bread and French pastries, and brewed coffees. Come for a late lunch or picnic for dinner.

 

Can I bring my pet? Well behaved pets are welcome. Please be sure to bring water and bags.

 

Where are restrooms? Restrooms are located within the splash park/playground area. There’s also a water fountain.

 

Can we have a picnic? By all means, grab some lunch from one of the vendors and find a shady spot. You may want to bring a blanket or lawn chair and an umbrella for the summer sun. The entire park and Market area, restrooms, and parking lots are wheelchair accessible.

View Event Page

Start: May 22nd 6:00 PM

End: May 22nd 11:00 PM

Truman Waterfront Park

End of Southard Street

Key West

FL

33040

X

Truman Waterfront Farmers Market

Community Event

Join us every Thursday from 2-7 p.m. for the Truman Waterfront Farmers Market. With a variety of vendors and things to do, it's fun for everyone!

 

When is the Farmer’s Market? Every Thursday, 2 p.m. to 7p.m., rain or shine (too much rain and they pack it up, though). The Market will continue as long as there is strong community support.

 

Who should go? The Key West Farmer’s Market is for locals and visitors alike. Residents will find quality items to stock the fridge and pantry, gifts and home décor while sampling fun new lunch choices. Vacationers will love shopping with a view, reasonable food options and plenty to see and do at the Park.

 

Where is the Farmer’s Market exactly? At the Truman Waterfront, end of Southard Street. Look for tents on the Quay by the USCG Ingham on the waterfront.

 

What does it cost? Entrance into the Park and Market is always free. Some vendors do not take credit cards. The closest ATM is at the Green Parrot.

 

Where is parking? There is a large City lot directly adjacent to the market with plenty of parking, handicapped spots, and bicycle racks.

 

What does parking cost? The City lot has pay stations that take credit card or cash. Rates are $4/hour or free for up to 4 hours with a Resident sticker. Handicapped spots are always free and are monitored.

 

Can I ride a bus? The Duval Loop conveniently stops at the round-about on the half hour. Download their app or check here for info.

 

What kind of vendors? Every week you’ll find traditional farmer’s market fare including produce, seasonal fruits, cheese, pickles, nuts, honey, seafood, fresh breads, hot sauces, and more. There are food stands and food trucks. Artists, crafters, flea market goods, jewelry, clothing/t-shirts, local organizations – cigars and CBD – it’s an eclectic group of small businesses who collectively offer one-stop shopping at our weekly pop-up island bazar.

 

What else is there to do at the park? The USCG Ingham is a self-guided maritime museum open Tuesday – Saturday 10 a.m. to 4 p.m. $10 adults/$5 kids/$5 active military. Truman Waterfront park features a splash park, playground, and lots of grass to spread out a picnic. Restrooms & shower rinse. The Quay faces the Gulf and often cruise ships and Navy cutters on duty will be parked nearby. There are plenty of park benches to enjoy the view (but little shade, umbrella recommended), Fort Zachary Taylor Beach & State Park is a National Historic Landmark on 54 acres and houses a civil war fortress and the best beach on Key West. Entrance fees start at $2.50 and up.

 

What kind of food options? There’s a little bit of everything week to week which may include Poke Bowls, Indian, Mediterranean, fresh fish and seafood, smoothies, bread and French pastries, and brewed coffees. Come for a late lunch or picnic for dinner.

 

Can I bring my pet? Well behaved pets are welcome. Please be sure to bring water and bags.

 

Where are restrooms? Restrooms are located within the splash park/playground area. There’s also a water fountain.

 

Can we have a picnic? By all means, grab some lunch from one of the vendors and find a shady spot. You may want to bring a blanket or lawn chair and an umbrella for the summer sun. The entire park and Market area, restrooms, and parking lots are wheelchair accessible.

View Event Page

Start: May 29th 6:00 PM

End: May 29th 11:00 PM

Truman Waterfront Park

End of Southard Street

Key West

FL

33040

X

Truman Waterfront Farmers Market

Community Event

Join us every Thursday from 2-7 p.m. for the Truman Waterfront Farmers Market. With a variety of vendors and things to do, it's fun for everyone!

 

When is the Farmer’s Market? Every Thursday, 2 p.m. to 7p.m., rain or shine (too much rain and they pack it up, though). The Market will continue as long as there is strong community support.

 

Who should go? The Key West Farmer’s Market is for locals and visitors alike. Residents will find quality items to stock the fridge and pantry, gifts and home décor while sampling fun new lunch choices. Vacationers will love shopping with a view, reasonable food options and plenty to see and do at the Park.

 

Where is the Farmer’s Market exactly? At the Truman Waterfront, end of Southard Street. Look for tents on the Quay by the USCG Ingham on the waterfront.

 

What does it cost? Entrance into the Park and Market is always free. Some vendors do not take credit cards. The closest ATM is at the Green Parrot.

 

Where is parking? There is a large City lot directly adjacent to the market with plenty of parking, handicapped spots, and bicycle racks.

 

What does parking cost? The City lot has pay stations that take credit card or cash. Rates are $4/hour or free for up to 4 hours with a Resident sticker. Handicapped spots are always free and are monitored.

 

Can I ride a bus? The Duval Loop conveniently stops at the round-about on the half hour. Download their app or check here for info.

 

What kind of vendors? Every week you’ll find traditional farmer’s market fare including produce, seasonal fruits, cheese, pickles, nuts, honey, seafood, fresh breads, hot sauces, and more. There are food stands and food trucks. Artists, crafters, flea market goods, jewelry, clothing/t-shirts, local organizations – cigars and CBD – it’s an eclectic group of small businesses who collectively offer one-stop shopping at our weekly pop-up island bazar.

 

What else is there to do at the park? The USCG Ingham is a self-guided maritime museum open Tuesday – Saturday 10 a.m. to 4 p.m. $10 adults/$5 kids/$5 active military. Truman Waterfront park features a splash park, playground, and lots of grass to spread out a picnic. Restrooms & shower rinse. The Quay faces the Gulf and often cruise ships and Navy cutters on duty will be parked nearby. There are plenty of park benches to enjoy the view (but little shade, umbrella recommended), Fort Zachary Taylor Beach & State Park is a National Historic Landmark on 54 acres and houses a civil war fortress and the best beach on Key West. Entrance fees start at $2.50 and up.

 

What kind of food options? There’s a little bit of everything week to week which may include Poke Bowls, Indian, Mediterranean, fresh fish and seafood, smoothies, bread and French pastries, and brewed coffees. Come for a late lunch or picnic for dinner.

 

Can I bring my pet? Well behaved pets are welcome. Please be sure to bring water and bags.

 

Where are restrooms? Restrooms are located within the splash park/playground area. There’s also a water fountain.

 

Can we have a picnic? By all means, grab some lunch from one of the vendors and find a shady spot. You may want to bring a blanket or lawn chair and an umbrella for the summer sun. The entire park and Market area, restrooms, and parking lots are wheelchair accessible.

View Event Page

Start: May 4th 2:00 PM

End: May 4th 8:00 PM

Key West Tropical Forest & Botanical Garden

5210 College Road

Key West

FL

33040

X

Locals Day at the Key West Tropical Forest & Botanical Garden

Community Event

On the first Sunday of each month, Florida Keys/Monroe County residents and students can enjoy free admission for to the Key West Tropical Forest and Botanical Garden. A Monroe County, Florida ID is required.

 

The Key West Garden is a special place where you can appreciate biodiversity and learn more about its importance. We are home to many endangered and threatened flora and fauna. Unlike traditional botanical gardens, this garden advocates the importance of native plants and species through education in a natural conservation habitat.

 

Bring the family, wander our nature trails, discover the secrets of our ponds, and explore. Bring your dog — on a leash, of course.

 

Plenty of free parking for bikes, scooters, and cars. Accessible trails and facilities.

 

For more information, call 305-296-1504 or visit keywest.garden.

View Event Page

Start: May 21st 11:00 PM

In person or via Zoom

X

History of Diving Museum: Free Immerse Yourself Presentation - Mistakes Divers Make by Dan Orr

Educational Event

Immerse Yourself!

Join us online or in-person!

Mistakes Divers Make

with Dan Orr, Diving Consultant and Former President of DAN(Divers Alert Network)

Dan Orr, President of Dan Orr Consulting, has more than 50 years of diving experience. He retired from the position of President of Divers Alert Network (DAN) where he helped focus DAN on its worldwide diving safety mission.

Dan has published and co-authored more than a dozen books and manuals including 101 Tips for Recreational Divers, Scuba Diving Safety, and the DAN Oxygen First Aid for Scuba Diving Injuries Training Manual. He has been the recipient of many prestigious awards and is a member of the Hall of Fame for Disabled Divers, the Diving Industry Hall of Fame, and the International Scuba Diving Hall of Fame. His seminar will take us through the incidence of injury in scuba diving and mistakes that divers make with recommendations on how to identify and mitigate these risks.

Thank you to this months sponsor: Trident Surface Supplied Diving.

Questions or concerns? E-mail programs@divingmuseum.org!

Wed | May 21st | 7 pm

View Event Page

Start: May 1st 2:00 PM

End: May 1st 5:00 PM

Frederick Douglass Community Center

111 Olivia Street

Key West

FL

33040

X

SBDC at FIU: Florida Keys New Business Launch Lab - Key West

Community Event

Are you ready to turn your entrepreneurial dreams into a thriving business? Join us for the "Florida Keys New Business Launch Lab in Key West", a comprehensive program designed to guide aspiring entrepreneurs through the essential steps of starting & growing your business.

 

Whether you have a solid business idea or are just beginning to explore the possibilities, this program will provide you with the knowledge, tools, and resources you need to successfully launch and grow your business.

 

Florida SBDC at FIU consultants will provide resources and one-on-one sessions to attendees on how to best launch their businesses.

 

Space is limited to 15 entrepreneurs so register today!!

View Event Page

Start: May 1st 3:00 PM

End: May 1st 6:00 PM

24 North Pool & Sunset Green Lawn

X

Hangover Recovery Pool Party

Community Event

Welcome to the Hangover Recovery Pool Party! Get ready to soak up the sun and cure those post-party blues with us at the 24 North Hotel in Key West. Join us on Thursday, May 1st, 2025 at 11:00 AM for a day of relaxation and fun by the pool. Bring your friends and enjoy refreshing drinks, good music, and great company. Let's make some new memories and recover from last night's festivities together. Don't miss out on this epic pool party!

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Start: May 4th 4:00 PM

End: May 4th 8:00 PM

The Gates Key West

3824 N Roosevelt Boulevard

Key West

FL

33040

X

Sunday Funday Fiesta at the Gates Hotel

Community Event

Welcome to the **Sunday Funday Fiesta** at The Gates Hotel Key West! Get ready for a day filled with fun, laughter, and good vibes. Join us on **Sunday, May 4th, 2025** starting at **12:00 PM** for a fiesta like no other. The event will take place at The Rum Row Pool at The Gates Hotel, where you can enjoy a beautiful setting and great company. Come and enjoy delicious food, refreshing drinks, and live music. Don't miss out on this opportunity to have an amazing time with friends and family. See you there!

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Start: May 13th 10:00 PM

The Studios of Key West

533 Eaton Street

Key West

FL

33040

X

Southernmost Youth Orchestra Spring Concert

Community Event

The Southernmost Youth Orchestra invites the community to enjoy their Spring Concert featuring talented young musicians from across the Keys. Admission is free and open to all ages. Bring the whole family for an evening of music and community spirit! 


Upcoming Concert Date:
    •    Tuesday, May 13 at 6:00 PM – The Studios of Key West, 533 Eaton Street

For more information, contact Irie Monte at southernmoststrings@gmail.com or (914) 523-1991

View Event Page

Start: May 11th 9:30 PM

The Marquesa Hotel & Café Marquesa

600 Fleming St

Key West

FL

33040

X

Mother's Day Dinner at Cafe Marquesa

Community Event

Mother’s Day Dinner

May 11, 2025  |  Seatings beginning at 5:30 pm

Enjoy indulgent dishes, decadent deserts and unique cocktails as you dine with refined Southern cuisine this Mother’s Day. Delight in our a la carte menu and Chef’s featured seasonal specials.

MOTHER’S DAY DINNER SPECIALS

Beet and Blueberry Salad $18
chevre, wild mushrooms, farm greens, cilantro vinaigrette

Jumbo Scallops $56
island root succotash, butternut squash, celeriac, bacon lardons, corn puree

Roast Chicken Breast $48
potato puree, sweet English peas, wild mushroom demi

Fruit Mille Feuille $18
mascarpone cheese, puff pastry, fresh fruit

Reserve on OpenTable

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Start: May 11th 1:00 PM

End: May 11th 6:00 PM

Hyatt Centric Key West Resort and Spa

601 Front Street

Key West

FL

33040

X

Mother's Day Brunch at Four Flamingos, A Richard Blais Key West Kitchen

Community Event

Mother's Day Brunch at Four Flamingos, A Richard Blais Key West Kitchen

Mother's Day Brunch

Celebrate Mom in Style at Four Flamingos! Join us for an unforgettable Mother's Day Brunch Buffett that you won't find anywhere else in Key West. Indulge in our lavish Noshing Table, delight in the freshest offerings from the Raw Bar, and savor selection from our carving stations. 

 

Bottomless Mimosas $28

Bottomless Bloody Mary's $28

 

$90++ Adults | $40++ Children 12 & Under  

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Start: May 8th 3:00 PM

History of Diving Museum

82990 Overseas Hwy

Islamorada

FL

33036

X

History of Diving Museum: Armed Forces Day Tours

Community Event

Join the History of Diving Museum at 11 AM and 2 PM for a special guided tour of the exhibits! The tour is included in your admission price. May’s tours will coincide with Armed Forces Day and the beginning of the Blue Star Museums program, which provides free admission to active duty military and up to six members of their families. These tours will feature special highlights of the extensive military history of diving.

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Start: May 21st 2:00 PM

End: May 21st 10:45 PM

History of Diving Museum

82990 Overseas Hwy

Islamorada

FL

33036

X

History of Diving Museum: Admission Specials - Love Our Locals!

Community Event

On Wednesday, May 21st, the History of Diving Museum will be extending free admission to all Islamorada residents. Be sure to take advantage of this offer by coming to see the grand opening of our new exhibit, Celebrating 20 Years! Featured exhibit. The Museum will be open from 10 AM to 6:45 PM, with the exhibit ribbon-cutting ceremony at 6:30 PM.

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Start: May 17th 3:00 PM

End: Sep 1st 4:00 AM

History of Diving Museum

82990 Overseas Hwy

Islamorada

FL

33036

X

History of Diving Museum: Admission Specials - Blue Star Museums

Community Event

To honor and thank those serving in the military, on Armed Forces Day the History of Diving Museum will hold complimentary guided tours included with your admission ticket. These will take place at 11 AM and 2 PM on Saturday, May 17. This date also marks the beginning of the 2025 Blue Star Museums Program, which offers free admission to active duty military and up to five members of their family. Blue Star Museums begins on Armed Forces Day, Saturday, May 17 and ends on Labor Day, Monday, September 1.

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Start: May 25th 4:00 PM

Schooner Wharf Bar at KW Seaport

202-R William Street

Key West

FL

33040

X

34th Annual Schooner Wharf Minimal Regatta

Annual Event

We hope to make a splash with our homemade vessels created out of plywood & duct tape. Build a Boat from Minimal Materials and Compete against Others in the Key West Bight. The Craziest Regatta You'll ever see, Join us for some wet and wacky fun!

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Start: May 25th 12:30 PM

The Marker Waterfront Resort

200 William Street

Key West

FL

33040

X

The Marker: The 1st Annual Salute to Service 5K

Annual Event

The Marker Salute to Service 5K

 

The Marker Resort celebrates our service members and is proudly partnering with the VFW 3911 and Good Vodka to bring you the First Annual Salute to Service 5K on Sunday, May 25th 2025 @ 8:30 am Starting at The Marker (200 William Street Key West, FL). The course will take runners and walkers through Old Town Key West and finish with a one of a kind pool party at the Marker!

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