Calendar of Events
May 2025: Florida Keys Events

- Sponsored Event
- May 2, 2025 - May 4, 2025 Islamorada Fishing
- 18th Annual Nick Sheahan Dolphin Rodeo
- Website
- 90800 Overseas Highway Tavernier FL 33070
- 305-393-3709 E-mail
Honoring the memory of Nick Sheahan, a Florida Keys student, this tournament benefits a namesake community scholarship fund that has distributed over $456,000 to Coral Shores High School students. The event features cash prizes for the top three adult anglers with the heaviest dolphin fish. If an angler breaks the Florida dolphin fish record (81 pounds) they win the grand prize. Tournament events held at Tavernier Creek Marina, mile marker 90.8 bayside. All proceeds to scholarships for graduating Seniors at Coral Shores High School! Friday night Kick Off Party. Music, Food, Drinks & Silent Auction. Non-Anglers welcome. $25,000 Cash Prize for angler who breaks the Dolphin State Record!
- Buy tickets! Call now!
- Dec 6, 2024 - May 18, 2025 Key West The Florida Keys Arts & Culture
- Key West Art & Historical Society: Collecting Key West – The Works of Mario Sanchez
- Website
Mario Sanchez (1908-2005), a Key West native, is among this country’s finest and most-recognized folk artists. In hundreds of intricately painted wood carvings created in a lifelong labor of love, Sanchez has provided a better history of Key West in the first part of the 20th century than any annals or academic texts. His bas-relief carvings, or intaglios, are a visual feast filled with the music, smells and passion of Gato’s Village, the Cuban-American community of Key West where Sanchez spent much of his life. In the carvings, each person, chicken, dog and fish has its own singular expression, attitude and identity. The exhibit is on display at the Custom House Museum daily from 10 a.m. to 5 p.m. 281 Front St.
- Mar 25, 2025 - May 5, 2025 Key West The Florida Keys Arts & Culture
- Key West Literary Seminar: Elizabeth Bishop’s Postcards, An Exhibition
- Website
In partnership with the Archives & Special Collections Library at Vassar College, Key West Literary Seminar presents Elizabeth Bishop’s Postcards, an exhibition of the beloved poet’s extensive postcard correspondence dating from her early life to her final years. Open March 25 to May 5, Tuesday-Wednesday-Thursday from 11am-2pm. 624 White St.
Friday, April 25 – 4-7:15pm – Opening Reception & discussion with exhibit curators Jonathan Ellis & Susan Rosenbaum
Saturday, April 26 – 9:30am-10:30am – Poetry reading, discussion with Dr. Heather White and KWLS executive director Arlo Haskell, postcard exhibition open to the public from 10:30am-3:30pm
- Apr 8, 2025 - May 3, 2025 Key West The Florida Keys Arts & Culture
- Red Barn Theatre: Short Attention Span Theatre – 2025 Edition
- Website
Fresh new, 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. Shows at 7:30 p.m. 319 Duval St.
- Apr 16, 2025 - May 3, 2025 Key West The Florida Keys Arts & Culture
- Waterfront Playhouse: Wait Until Dark
- Website
The final show of the Waterfront Playhouse’s Mainstage Series this season is Frederick Knott’s classic suspense drama “Wait Until Dark.” 407 Wall St. at Mallory Square.
- Apr 30, 2025 - May 4, 2025 Key West The Florida Keys Arts & Culture
- 29th Annual Key West Songwriters Festival
- Website
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.
- May 1, 2025 - May 4, 2025 Islamorada The Florida Keys Environmental
- I.CARE: Trash Derby & Festival
- Website
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.
- May 1, 2025 - May 29, 2025 Key West The Florida Keys Arts & Culture
- Studios of Key West: Isaac Valdes – The Way it Was
- Website
Experience the historical charm and vibrant culture of Old Key West through intricate wood carvings. This exhibition captures the essence of Key West’s bygone days, depicting its unique architecture, lush landscapes, and colorful local life. 533 Eaton St.
- May 2, 2025 - May 4, 2025 Marathon The Florida Keys Fishing
- Marathon Offshore Bull and Cow Dolphin Tournament
- Website
A guaranteed $18-thousand in cash awaits the top anglers who catch the largest bull and cow dolphin fish combined, while other prizes are awarded to anglers for 1st through 3rd place catches of the largest bull dolphin, largest cow dolphin, 3 largest dolphin combined, and the largest wahoo, tuna and tripletail. Tournament rules pick-up and weigh-ins at Two Conchs Bait & Tackle, 11499 Overseas Highway. Sunday evening awards banquet at Florida Keys Aquarium Encounters, 11587 Overseas Highway.
- May 8, 2025 - May 24, 2025 Marathon The Florida Keys Arts & Culture
- Marathon Community Theater: The Siegel
- Website
The story follows lovesick Ethan who plans to ask Alice’s parents for permission to marry her, but there’s one catch. Ethan and Alice broke up two years ago. Alice, reeling from having worked for a failed political candidate, is seeing someone else, but Ethan remains undaunted.
- May 8, 2025 - May 8, 2025 Key West
- Truman Waterfront Farmers Market – Every Thursday
- Website
Shop with a view every Thursday from 2 to 7 p.m. at the Truman Waterfront Farmers Market located on the harbor by the USCG Ingham Museum. Find great food options including ready-to-eat items, fresh Florida produce and other grocery items, along with gifts, home decor, art and more. Located at the corner of Southard Street and Weech Way.
- May 9, 2025 - May 10, 2025 Marathon The Florida Keys Fishing
- 19th Annual Mother’s Day Dolphin Tournament – Fish for a Cause
- Website
Cash prizes will be awarded for the heaviest mahi and to anglers who finish first through third place in this popular, family friendly annual fundraising tournament. There are four angler categories for prizes: professional, weekend warrior, lady, and junior angler. There is to be a captain’s meeting Friday night and one day of fishing on Saturday, followed by an awards banquet Saturday night. The “Fish for a Cause” event benefits Habitat for Humanity of the Middle Keys. Detailed information is available at www.mothersdaydolphintournament.com.
- May 9, 2025 - May 9, 2025 Key West The Florida Keys Arts & Culture
- Key West Outdoor Movies
- Website
Key West Outdoor Movies presents a family-friendly film (to be named) at the parade grounds at Fort East Martello, 3501 S. Roosevelt Blvd. The grounds open at 5 p.m. with free admission. Food and drink will be available for sale by vendors onsite, and there will be free popcorn and activities for all. Bring low chairs or a blanket. The movie starts at dusk. This is the season finale for Outdoor Movie Night
- May 9, 2025 - May 9, 2025 Key West The Florida Keys Arts & Culture
- Key West Theater: Paula Poundstone
- Website
Iconic comedian Paula Poundstone is known for her smart, observational humor and a spontaneous wit that has become the stuff of legend. She performs at Key West Theater for one night. The show, originally scheduled for Jan. 9, was rescheduled due to the California fires. Doors open 7 p.m.; show at 8 p.m. 512 Eaton St.
- May 11, 2025 - May 11, 2025 Key West The Florida Keys Recreation
- Sheriff’s Animal Farm Open House
- Website
Visit the family-friendly Monroe County Sheriff’s Animal Farm, open the second and fourth Sundays of each month from 1 to 3 p.m. Animals include a capybara, possum, sloths, goats, birds and many more. Visits are free of charge, but donations of cash or fresh produce are always welcomed. Stock Island Detention Center, 5501 College Rd.
- May 15, 2025 - May 15, 2025 Key West
- Truman Waterfront Farmers Market – Every Thursday
- Website
Shop with a view every Thursday from 2 to 7 p.m. at the Truman Waterfront Farmers Market located on the harbor by the USCG Ingham Museum. Find great food options including ready-to-eat items, fresh Florida produce and other grocery items, along with gifts, home decor, art and more. Located at the corner of Southard Street and Weech Way.
- May 15, 2025 - May 15, 2025 Islamorada The Florida Keys Arts & Culture
- Morada Way Third Thursday Art Walk
- Website
The Morada Way Arts & Cultural District’s Third Thursday Art Walk in Islamorada is the organization’s landmark, monthly event. This Thursday, enjoy a holiday-flavored edition of the art walk with Keys-inspired fine artists, vendors, residents, and visitors congregating on Morada Way in Islamorada. Enjoy a relaxing evening from 6-9 p.m. perusing local fine art, imbibing local craft beer and wine and listening to music, in the area between mile markers 81 and 82 at 151 Morada Way.
- May 15, 2025 - May 15, 2025 Key West The Florida Keys Arts & Culture
- Walk on White Third Thursday Art Walk
- Website
Explore an array of arts-focused offerings at more than 20 locations showcasing the works of painters, photographers, sculptors, ceramic and mixed media artists, and artisan jewelry makers at this monthly third Thursday event from 6 to 9 p.m. Take in views of beautiful island architecture, exhibit openings, creative demonstrations, musical, literary and performance offerings and complimentary libations. White Street between Southard and United Streets.
- May 15, 2025 - May 15, 2025 Key West The Florida Keys Arts & Culture
- Key West Theater: Duane Betts & Palmetto Motel
- Website
Duane Betts, son of Dickey Betts of Allman Brothers Band fame, performs guitar-slinging, story-driven American rock and roll along with Palmetto Motel. Doors open 7 p.m.; show at 8 p.m. 512 Eaton St.
- May 16, 2025 - May 18, 2025 Islamorada The Florida Keys Fishing
- ‘Ladies Let’s Go Fishing’ Screamin’ Reels Tournament
- Website
Intended for novice anglers and returning participants, this weekend is about learning and a non-intimidating, fun competition with the “Ladies Let’s Go Fishing” university organizers. Participants can join on a professional charter boat or fish on their own boat. This is a casual tournament with prizes for the heaviest offshore fish and longest inshore fish, drawings for prizes for those who caught fish, plus bonus drawings. The Friday kickoff takes place at The Tavernier Elks Club, mile maker 92 bayside; most Saturday and Sunday charters depart from Whale Harbor Marina, mile marker 83 oceanside.
- May 17, 2025 - May 18, 2025 The Florida Keys Recreation
- Keys100 Ultramarathon Races
- Website
Keys 100 is a 100-mile point-to-point running race from Key Largo to Key West. Both teams and individuals compete. There is also a 50-mile option from Marathon to Key West and a 50k individual race from Big Pine Key to Key West. All races finish at Higgs Beach on the Atlantic in Key West. 100-mile races start at Divers Direct in Key Largo, MM 99.8, and 50-mile races start at Marathon Garden Club.
- May 17, 2025 - May 17, 2025 Islamorada Diving
- Armed Forces Day Tours: History of Diving Museum
- Website
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.
- May 17, 2025 - Sep 1, 2025 Islamorada Diving
- Blue Star Museums: History of Diving Museum
- Website
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.
- May 18, 2025 - May 21, 2025 Islamorada Fishing
- Golden Fly Invitational Tarpon Tournament
- Website
The Golden Fly Tournament attracts top fly anglers and world class guides to test their abilities in Islamorada during the famed tarpon migration. The 3-day, invitation only tournament launches from the Lorelei Restaurant & Marina, 96 Madeira Rd.
- May 21, 2025 - Dec 31, 2025 Islamorada The Florida Keys Diving
- History of Diving Museum Presents – Celebrating 20 Years! Featured Exhibit
- Website
The History of Diving Museum’s new limited-time featured exhibit is open to the public! Starting May 21st, dive into the Museum’s 20th Anniversary Special Exhibit to learn about what it took to create the world’s largest collection of diving equipment on public display, how the Museum has evolved and grown over the past two decades, and what visitors have to look forward to in the future. Info: (305) 664-9737; www.divingmuseum.org
- May 21, 2025 - May 21, 2025 Islamorada Diving
- Love Our Locals: History of Diving Museum
- Website
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.
- May 21, 2025 - May 21, 2025 Islamorada Diving
- Free Immerse Yourself! Mistakes Divers Make
- Website
Join the History of Diving Museum as it hosts Dan Orr, dive professional and former president of DAN, or Divers Alert Network, as he takes us through common mistakes divers make and different hazards faced in both commercial and recreational diving. Presentation will be in-person and take place at 7 PM on May 21st at the History of Diving Museum, 82990 Overseas Hwy (MM 83 Bayside). Be sure to come early for the Museum’s extended hours and see the grand opening of Celebrating 20 Years! Featured Exhibit. Donations welcome. Info: (305) 664-9737; www.divingmuseum.org
- May 22, 2025 - May 22, 2025 Key West
- Truman Waterfront Farmers Market – Every Thursday
- Website
Shop with a view every Thursday from 2 to 7 p.m. at the Truman Waterfront Farmers Market located on the harbor by the USCG Ingham Museum. Find great food options including ready-to-eat items, fresh Florida produce and other grocery items, along with gifts, home decor, art and more. Located at the corner of Southard Street and Weech Way.
- May 25, 2025 - May 25, 2025 Key West The Florida Keys Recreation
- Sheriff’s Animal Farm Open House
- Website
Visit the family-friendly Monroe County Sheriff’s Animal Farm, open the second and fourth Sundays of each month from 1 to 3 p.m. Animals include a capybara, possum, sloths, goats, birds and many more. Visits are free of charge, but donations of cash or fresh produce are always welcomed. Stock Island Detention Center, 5501 College Rd.
- May 29, 2025 - May 29, 2025 Key West
- Truman Waterfront Farmers Market – Every Thursday
- Website
Shop with a view every Thursday from 2 to 7 p.m. at the Truman Waterfront Farmers Market located on the harbor by the USCG Ingham Museum. Find great food options including ready-to-eat items, fresh Florida produce and other grocery items, along with gifts, home decor, art and more. Located at the corner of Southard Street and Weech Way.
- May 30, 2025 - Jun 1, 2025 Key Largo The Florida Keys Fishing
- 11th Annual Skippers Dolphin Tournament
- Website
This highly competitive, family-friendly tournament is headquartered at Skippers Dockside Restaurant behind Key Largo’s Holiday Inn at mile marker 100. Cash prizes of over $50,000 include a first-place prize of $20,000 as well as prizes for the top six teams and top lady and junior anglers.