Events in the Florida Keys

Event calendar provided with the courtesy of the Monroe County Tourist Development Council.

Events in Florida Keys for 2024

  • January 17 - April 17 Islamorada
  • History of Diving Museum: Dive into Art - Coral Creations
  • Website
  • See the History of Diving Museum's featured exhibit, "Dive Into Art: Coral Creations." The exhibit showcases art from across the Florida Keys, including works from local schools and members of the Art Guild of the Purple Isles. Each piece focuses on a theme of coral conservation, with educational interpretation provided by local coral conservation groups.

  • February 23 - April 28 Key West
  • Key West Art & Historical Society: Shadow & Light Art Exhibit
  • Website
  • The juried exhibit, "Shadow & Light" celebrates the work of over 50 Keys artists who contributed works in a variety of mediums that capture the natural light of the Florida Keys. These visual expressions evoke contemplation, wonder and introspection. The exhibition runs through April 28 in the Bryan Gallery at the Custom House Museum, 281 Front Street.

  • April 09 - April 27 Key West
  • Red Barn Theater: The Lifespan of a Fact
  • Website
  • With a deadline looming, a talented writer, a desperate magazine editor and a young aggressive fact checker go head-to-head in this oh-so-funny and gripping dispute over factual truth vs. the beauty of literary dishonesty. Showtime 7 p.m. 319 Duval St.

  • April 14 - April 14 Key West
  • Key West Artisan Market: Ocean Awareness Edition
  • Website
  • Shop a curated outdoor market displaying delicious culinary creations, fresh produce, fine crafts, art, jewelry and more from talented Florida Keys makers. Listen to awesome local musicians, meet talented local authors and support the market's featured cause. This week, you're invited to support Ocean Awareness. Reef Relief will be there to help you lean ways to improve and protect our oceans, and would appreciate your donations. The market offers a full bar and is open 10 a.m to 2 p.m. in Sonny McCoy Indigenous Park, 1801 White St.

  • April 14 - April 14 Islamorada
  • Islamorada Community Entertainment: Bay Jam
  • Website
  • The 29th annual Bay Jam takes over the amphitheater at Founders Park, mile marker 87 bayside, from 11 a.m. to 8 p.m. The art and music festival features a full days' lineup of musicians along with art, craft and food and beverage vendors. Admission to the performances and Bay Jam is free but there is a $10 charge for parking.

  • April 14 - April 14 Big Pine Key
  • 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. Visits are free of charge, but donations are always welcomed. Stock Island Detention Center, 5501 College Rd.

  • April 14 - April 14 Marathon
  • Marathon Community Theatre: Drag Queen Bingo
  • Website
  • Drag Queen Bingo is back with the theme Black Widow. Costumes are welcomed but not required. Doors and concessions open 4 p.m.; bingo from 5 to 7 p.m. $10 admission. 5101 Overseas Highway.

  • April 16 - April 16 Key West
  • Connections Project: Key West Reception
  • Website
  • For years, the Florida Keys Council of the Arts has gathered mini-canvases from area artists to create one large Keys art mural/mosaic its annual Connections Project. This year, the council created five separate murals and, at each opening reception in each region of the Keys, is including live music to create a multi-faceted celebration of the artistic spirit that makes the Keys so special. The free Key West reception on April 16 culminates the Connections Project. It takes place from 5 to 7 p.m. at Williams Hall, 729 Fleming St. Attendees may purchase their choice of individual canvases from the mosaic for $100 each.

  • April 17 - April 27 Key West
  • Fringe Theater: Death and the Maiden
  • Website
  • A white-knuckle thriller and riveting tug-of-war. Who do you believe - your deeply troubled spouse, or your new persuasive friend? Winner of the 1992 Olivier Award for Best New Play. Tickets $45-$60. 7 p.m. at the Armory, 600 White St.

  • April 18 - April 18 Islamorada
  • 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. On the Third Thursday of each month, Keys-inspired fine artists, vendors, residents, and visitors congregate on Morada Way in Islamorada to celebrate the arts and culture in the Florida Keys. 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.

  • April 18 - April 20 Marathon
  • Marathon Premier Sailfish Tournament
  • Website
  • This sailfish challenge benefits Mission Fishin’, a South Florida nonprofit that helps fund marine adventures for foster children, kids with special needs, and their families. Prizes are to be awarded to the top three boat teams and top male, female and junior anglers among others. Tickets are available for non-anglers to attend the awards banquet and fundraising auction, Saturday, April 20th, 6:30 to 9 p.m. at Florida Keys Aquarium Encounters, mile marker 53 bayside.


  • April 18 - April 28 Key Largo
  • Key Players: Escape to Margaritaville
  • Website
  • Jimmy Buffett’s "Escape to Margaritaville" is a musical comedy featuring the most-loved Jimmy Buffett classics, including “Cheeseburger in Paradise”, “Margaritaville,” “It’s Five O’Clock Somewhere,” “Fins,” “Volcano,” and many more. This hilarious, heartwarming musical is the party you’ve been waiting for. Shows dates are April 18, 19 and 20; and 25, 26, and 27 at 7 p.m., with a 2 p.m. Sunday matinee April 28. Performances at Murray Nelson Government Center, MM 102 bayside.

  • April 18 - April 18 Key West
  • Key West Theater: Rock 'n Roll Burlesque Show
  • Website
  • Key West Burlesque presents the Rock 'n Roll Bulesque Show, an immersive night of rock music and mesmerizing performances. The show features rock and roll hits of the 1960s, 70s, 80s and 90s played by the Mark King Band. Doors open at 7 p.m; show at 8 p.m. Tickets available online and at the box office at 512 Eaton St.

  • April 19 - April 19 Marathon
  • Marathon Community Theater: Dramatic Wine Tasting
  • Website
  • This wine tasting is not so much for serious wine drinkers, but more for fun-loving wine drinkers. Participate in a blind taste test of red wines to determine which wine is your favorite, and try to identify what type of wine it is. $10 cash entry fee includes four sample wine pours and light snacks. There will also be a cash bar. 6 to 7 p.m. 5101 Overseas Highway.

  • April 19 - April 19 Key West
  • Conch Republic Day Independence Celebration: Conchy Beach Cleanup
  • Website
  • Join other citizens of the Conch Republic for the annual Conchy Beach Cleanup, a fun way to meet others and to help kick off the annual celebration of Independence in the Florida Keys. Show up and tools will be provided for you. Meet at the Key West Bocce Court parking lot, 1801 White St. The cleanup begins at 8 and runs until 9 a.m. Organized by Plogging the Keys and Help Keep the Conch Republic Beautiful.

  • April 19 - April 19 Key West
  • Conch Republic Independence Celebration: Opening Ceremony and Kick-Off Party
  • Website
  • The annual celebration of the creation of the Conch Republic's official opening ceremony takes from 5 to 6 p.m. at Mallory Square, 400 Wall St. That is followed by the official Kick-Off Party and Conch Shell Blowing Contest at Schooner Wharf Bar, 202 William St., beginning at 7 p.m. Both events are open to the public with no ticket required.

  • April 19 - April 28 Key West
  • 42nd Annual Conch Republic Days
  • Website
  • Fans and friends of the Florida Keys’ Conch Republic can celebrate the irreverent "nation's" 42nd birthday with activities including a tall ship pirate adventure, traditional shrimp boil, sunset boat parade, tour of the USCGC Ingham floating maritime museum, reenactment of the Great Sea Battle of the Conch Republic, the World's Longest Parade, Drag Races on Duval Street and more. The annual Conch Republic Independence Celebration commemorates the Keys’ symbolic 1982 secession from the United States and reinvention as the eccentric republic.

  • April 20 - April 20 Key West
  • Mote Marine Laboratory: Ocean Fest - A Community Celebration
  • Website
  • Underwater and outdoor enthusiasts, eco-travelers and families are encouraged to celebrate Earth Day and the marine environment during a fun day of crafts, games, music, food, local brews and shopping. There will be two kids' fishing clinics for children age 7-12 fro 11 a.m. to 1 p.m. and also 2 to 4 p.m. The Keys' treasured marine environment will be showcased along with raising money for coral reef research, restoration and conservation. Attendees can explore conservation and environmental exhibits, meet Mote scientists and learn how you can help.

  • April 20 - April 20 Big Pine Key
  • Bahia Honda State Park Earth Day Celebration
  • Website
  • Learn about earth-friendly activities and practices from numerous conservation-minded vendors and enjoy live music, touch tanks, games and crafts. A scavenger hunt will send kids on a journey to visit the festival’s many exhibitors. The park adopted the global Earth Day theme for this year’s event, “Planet vs. Plastic,” with a focus on joining together in partnership to protect our planet by embracing practices that promote a sustainable and healthy environment.

  • April 20 - April 20 Islamorada
  • Swim Across America: Florida Keys Open Water Swim
  • Website
  • The Swim America Florida Keys Open Water Swim raises funds that go directly to cancer research and patient care programs at Miami Cancer Institute. Each participating swimmer age 18 and over is asked to raise a minimum of $500, and those under 18, a minimum of $200. Swimmers can elect to swim alone or as part of a team. Distance options are 1/2 mile; 1 mile; and 2 miles. The event takes place at Founders Park, mile marker 87 bayside. Swimming starts at 9:45 a.m. and there is to be a post-event celebration on the Founders Park beach at 11:15 a.m.

  • April 20 - April 20 Big Pine Key
  • Stock Island Earth Day Cleanup
  • Website
  • Join this annual cleanup around Stock Island that takes place during the Conch Republic Independence Celebration from 8 a.m. to noon on Saturday in celebration of Earth Day. Stop by Bernstein Park at 6751 5th St. to pick up vests, pokers and buckets. Stop by whenever you can and spend as much or as little time as you have to volunteer.

  • April 20 - April 20 Key West
  • Earth Day 5k Run/Walk
  • Website
  • The Key West Southernmost Runners' 26th annual Earth Day 5k Run/Walk takes place Saturday at Truman Waterfront Park at the end of Southard St. The start and finish line is near the U.S .Coast Guard Cutter Ingham Maritime Museum. Proceeds from the race benefit the Conch Republic Marine Army, a local non-profit grassroots organization dedicated to cleaning and restoring the shallow mangrove habitats of the Florida Keys. Registration is $25 per person (free for children under 5 with a parent). Participants can register online or in person at the race location from 5 to 7 p.m. April 19, and at 7 a.m. April 20 before the 8 a.m. race start.

  • April 20 - April 20 Big Pine Key
  • Plant a Million Corals: Earth Day Celebration & Mangrove Planting
  • Website
  • Join the teams from Plant a Million Corals and Coastlove at Summerland Farms, mile marker 23.8 bayside, for an Earth Day open house. It will be a day of music, refreshments, fun educational activities, tours of the coral and mangrove nurseries, and you will also get the chance to plant baby mangroves. The Monroe County Fire Department will be onsite with their famous snow cones. The event is free.

  • April 21 - April 24 Islamorada
  • Herman Lucerne Memorial Tarpon Cup
  • Website
  • The prestigious, Islamorada-based Herman Lucerne Memorial Tarpon Cup features guided anglers competing in the Everglades backcountry to catch and release the most tarpon in support of ecosystem preservation and improvement.

  • April 21 - April 21 Marathon
  • Marathon Community Theater: A Concert for Kids featuring Mateo
  • Website
  • This family-friendly concert featuring internationally-acclaimed guitarist Mateo is a child’s introduction to multiple forms of music played on classical guitar, including classical, Spanish, folk, flamenco, blues, Latin and traditional. Adults $15; kids free. 5101 Overseas Highway.

  • April 22 - April 22 Key West
  • Earth Day Jam with That Hippie Band
  • Website
  • Groove to the music of the 60s and 70s focused on environmental protection with That Hippie Band. Doors open at 6 p.m.; show at 7 p.m. Tickets available online or at the theater box office at 512 Eaton St.

  • April 22 - April 22 Key West
  • Plogging the Keys: Earth Day Cleanup at US 1 and Cow Key Channel Bridge
  • Website
  • Join other volunteers for an Earth Day Cleanup event Sunday morning from 8 to 9 a.m. of the area around US 1, the Triangle, the Cow Key Channel Bridge and surrounding streets. Meet alongside Tavern N Town and US 1 to pick up your vest, gloves, bucket and picker. One hour makes a huge difference, so start your day by taking part! After the cleanup, Tavern N Town will provide breakfast and coffee to all volunteers.

  • April 22 - April 22 Big Pine Key
  • Conch Republic Independence Celebration: K-9 Muster Party
  • Website
  • Calling all Canines – We want You! The Conch Republic Military’s K-9 Unit joins forces with the Florida Keys SPCA for the annual Reenlistment and Recruitment Muster, where one of the K-9 Corps members will win the "‘Best in Show" Prize for their combat gear. Each canine’s $25 annual K-9 Corps membership fee includes the muster, doggie bags with goodies, small nibbles for pups, and Yappy Hour prices for their handlers, and is required to participate in the Thursday Conch Republic Longest Parade K-9 Corp Crew. Costume judging at 6pm. The festivities take place at Bad Boy Taqueria at the Perry Hotel, 7011 Shrimp Rd., Stock Island.

  • April 22 - April 22 Key West
  • Reef Relief: Earth Day Key West Cleanup
  • Website
  • Visitors are invited to join locals and the team from Reef Relief for an Earth Day cleanup from 9 to 11 a.m. Meet at the stage in front of the Edward B. Knight (White Street) Pier. The first 100 participants will receive a free pair of flip flops.

  • April 23 - April 23 Big Pine Key
  • Florida Keys Wildlife Society: Full Moon Kayak Excursion
  • Capt. Bill Keogh 305-872-7474 Website
  • This kayak excursion, sponsored by Captain Bill Keogh of Big Pine Kayak Adventures, takes place from 6:30 to 8:30 p.m. in the waters surrounding the National Key Deer Refuge in Big Pine Key. The trip begins at Old Wooden Bridge Marina, 1791 Bogie Road, and proceeds across the water to No Name Key and north. Call or text Captain Bill at 305-872-7474 to reserve your spot and your kayak and gear. Cost is $30, which is a donation to Florida Keys Wildlife Society.

  • April 23 - April 23 Key Largo
  • Trashy Tuesday Cleanup at Harry Harris Park
  • Website
  • Sereia Films, an educational non-profit organization, is holding a "Trashy Tuesday" cleanup of the mangrove shoreline at Harry Harris Park, 50 E. Beach Rd, on the oceanside of U.S. 1, from 6 to 7 p.m. Be sure to wear closed-toed shoes and bring a reusable water bottle. Gloves, garbage bags, buckets and water refills will be provided. Contact the organizer online to RSVP.

  • April 23 - April 24 Key West
  • Studios of Key West: Abbie Gardner in Concert
  • Website
  • Abbie Gardner is a fiery dobro player with an infectious smile. Whether performing solo or with Americana group Red Molly, her acclaimed tales of love and loss, both gritty and sweet, are propelled by her impeccable slide guitar playing. Her live show is truly unique—as an award-winning songwriter, captivating vocalist, and a world-class lap style dobro player, she has an unmistakable sound all her own. Wednesday night's show starts at 8 p.m. on the roof at Hugh's View; Thursday night's show is 7 p.m. in Helmerich Theater. 533 Eaton St.

  • April 24 - May 11 Key West
  • Waterfront Playhouse: Lost in Yonkers
  • Website
  • Neil Simon's story, set in 1942 Brooklyn, of two brothers, Jay and Arty, who must learn to live with their stern Grandma, their Aunt Bella, and their Uncle Louie, a henchman for some gangsters. Showtimes at 8 p.m. with a Saturday 2 p.m. matinee on May 4. Tickets $40 to $85. 407 Wall Street at Mallory Square.

  • April 25 - April 25 Key West
  • Tennessee Williams Theatre: Les Ballets Trockadero de Monte Carlo
  • Website
  • The world-renowned, all-male Les Ballets Trockadero de Monte Carlo visits Key West to present a brilliant combination of skillful ballet movements and hilarious parodies of classic ballets such as Swan Lake. Founded in New York in 1974, the company, affectionately known as the Trocks, began by performing late-night in Broadway lofts to small audiences who appreciated the ensemble’s iconoclastic humour. In the 50 years since, the company has grown to appeal to an ever-growing audience who flock to theatres around the world each season to see these "prima ballerinas" perform. Tickets $35 to $135. Show at 8 p.m. 5901 College Rd.

  • April 26 - April 28 Marathon
  • 7-Mile Offshore Grand Prix
  • Website
  • Now in its second year, this spectacular race event from Race World Offshore offers excitement and heart-pounding action in the Gulf of Mexico, with viewing of the entire race course available from the pedestrian-friendly Old Seven Mile Bridge. The race is the kick-off event in the American Powerboat Racing Association National Series.


  • April 26 - April 26 Big Pine Key
  • Free Fishing Seminar
  • Website
  • Enjoy a free fishing seminar filled with tips and techniques from Lower Keys fishing guides. 5 to 7 p.m. at Island Welcome Real Estate, 24437 Overseas Highway bayside. There will also be food, drinks, fish art and more.

  • April 27 - April 27 Marathon
  • Leadership Monroe Spring GradFest
  • Website
  • Leadership Monroe County will celebrate its Class 31 graduation with the Leadership Spring GradFest, a community festival and alumni reunion to be held from 11 a.m. to 8 p.m. at Marathon Community Park, MM49. The family-friendly event features multiple food trucks, games, a bounce house, water slide, a classic car show, axe throwing booth, the Key West Police Mounted Patrol Unit, all-day music, artists and non-profit exhibit booths, a raffle, class graduation ceremony and more. Admission $10; children 12 and under free.

  • April 27 - May 03 Marathon
  • Tarponian Tournament
  • Rules of this high-energy three-evening tournament mandate that each team fishes with a different captain each outing. Teams also rotate among the three major bridge channels in Marathon, so any potential “hot spots” are shared among all anglers. The tournament's opening and closing events take place at Florida Keys Steak & Lobster House, mile marker 48 bayside. Call 267-210-1952 for information.

  • April 27 - April 27 Islamorada
  • Pops in the Park: Sci-Fi Serenade
  • Website
  • The free Florida Keys Community Concert Band performance on Sat. April 27 is themed: "Sci-Fi Serenade." The program includes selections from “Music of the Spheres” along with space movie music. Come dressed to impress in your sci-fi best for an out-of-this-world costume contest. Bring chairs and blankets for seating.

  • April 28 - April 28 Key West
  • Schooner Wharf Bar: Wrecker's Cup Race
  • Website
  • The final race of the 39th annual Wrecker's Cup Race Series to Sand Key kicks off Sunday at 1 p.m. The all-in-fun race series recalls the tradition of the wreckers from Key West in the 1800s. All sailing vessels, local sailors and visiting yachtsmen are welcome to join the regatta. Spectators can view from Schooner Wharf and the Historic Seaport. After the race, first, second and third place will be awarded in each division, with trophies, a bottle of Pusser’s rum, Schooner Wharf Bar tabs and wrecker T-shirts as prizes. Find Schooner Wharf Bar at 202 William St.

  • April 28 - April 28 Key West
  • Coffee Butler Amphitheater: The Price is Right Live
  • Website
  • The Price Is Right Live is the hit interactive stage show that gives eligible individuals the chance to hear their names called and "Come On Down" to win. Prizes may include appliances, vacations and possibly a new car! Play classic games just like on television's longest running and most popular gameshow...from Plinko to Cliffhangers to The Big Wheel and even the fabulous Showcase. Playing to near sold-out audiences for more than 20 years, the Price Is Right Live has entertained millions of guests and given away more than 15 million dollars in cash and prizes. Tickets start at $60. Showtime 8 p.m. 21 Quay Rd.

  • April 28 - April 28 Big Pine Key
  • 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. Visits are free of charge, but donations are always welcomed. Stock Island Detention Center, 5501 College Rd.

  • April 28 - April 28 Key West
  • Key West Artisan Market: Conch Republic Edition
  • Website
  • This is the last Artisan Market of the season until November and is a special salute to the Conch Republic. Shop a curated outdoor market displaying delicious culinary creations, fresh produce, fine crafts, art, jewelry and more from talented Florida Keys makers. Listen to awesome local musicians and meet talented local authors. The market offers a full bar and is open 10 a.m to 2 p.m. in Sonny McCoy Indigenous Park, 1801 White St.

  • April 28 - April 28 Key West
  • Coffee Butler Amphitheater: The Price is Right Live
  • Website
  • Come on down! The Price is Right Live comes to Key West's Coffee Butler Amphitheater April 28. Ticket holders will have the chance to register to be a contestant and play to win valuable prizes. If you're a fan of The Price is Right on TV, you're going to love this exciting, live (non-televised) version of the show.

  • May 01 - May 05 Key West
  • 28th 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. The opening night headliner on Duval Street May 1 is Dylan Marlowe; Cole Swindell Performas May 2 in a ticketed concert at Coffee Butler Amphitheater, and many more shows to be announced.

  • May 02 - May 02 Key West
  • Studios of Key West: First Thursday Open House
  • Website
  • During the First Thursday Open House event, the Studios keep the lights on late and throw the doors open to celebrate the newest work in its galleries. Stop in to say hello, relax with a glass of wine on the rooftop terrace, tour the third floor artist studios and see the just-installed exhibitions in the various galleries. 6 to 8 p.m. at 533 Eaton St.


  • May 02 - May 05 Key West
  • I.CARE: Trash Derby & Festival
  • Website
  • I.CARE’s Trash Derby, sponsored by the National Marine Sanctuary Foundation in support of Goal: Clean Seas, will begin with a team leader meeting Thursday, May 2 from 6:15 to 7:30 p.m. at Bud N'Mary's Marina. Trash collection activities will take place from sunrise to sunset from Key Largo to Key West May 3 and 4. Divisions include dive operators, private boat owners, and land lovers. Participation is open to everyone including visitors and community members. The Marine Sanctuary sponsorship this year allows dive charter participants to dive for FREE! Each diver will be entered to win excellent dive gear to be drawn at the Trash Derby Festival on Sunday, May 5. The free festival takes place 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 03 - May 05 Marathon
  • 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 03 - May 05 Islamorada
  • Nick Sheahan Dolphin Rodeo
  • Website
  • Honoring the memory of Nick Sheahan, a Florida Keys student, this tournament benefits a namesake community scholarship fund that has distributed over $408,000 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 of $25,000. Register in advance online until April 29. Walk-up registration is available at the May 3, Friday night cookout and captains meeting at Tavernier Creek Marina, mile marker 90.8 bayside.

  • May 03 - May 03 Key West
  • The Studios of Key West: Gallery Talk with Artist Anthony Mancuso
  • Website
  • Mancuso’s work focuses on how domestic spaces fit into Florida’s light and landscape, distorting and rendering them with unnatural color to convey the psychological experience of the Sunshine State. The talk takes place int he Sanger Gallery, where Mancuso's "Florida Room" exhibit is on display. The talk is free but RSVPs are requested.

  • May 04 - May 11 Marathon
  • Bob Traa Faro Blanco Tarpon Tournament
  • Website
  • Newly renamed to honor tournament founder Bob Traa, this team event allows two to four anglers per team/boat, who fish three nights with three different captains at three different bridges: Bahia Honda, Long Key and the world-famous Seven Mile. Proceeds from the charity tournament benefit Ronald McDonald House. Contact Donna Vankirk at 305-393-0699 or [email protected].

  • May 04 - May 04 Key West
  • Cow Key Bridge Run: Cow Wars 2024 - May the 4th Be With Moo!
  • Website
  • Dress up in your best bovine costume and trek across the infinitely short Cow Key Channel Bridge. Get in the MOO-d from 9 to 11 a.m. before the "race" at the Bloody MOO-ey party at the Rum Row bar at The Gates Hotel. The entire herd will move over to stage at the starting area in front of the bridge between 11 a.m. and 12 p.m. At 12 noon, the race starts with cows away! Everyone is invited back to Rum Row and the Sunset Green Lawn for an after-race party and awards ceremony. Sign-up includes a race bib. Commemorative T-shirts will be available for purchase at the pre-race party. All proceeds benefit the MCSO Animal Farm and the Highgate Foundation.

  • May 04 - May 04 Islamorada
  • Ziggy & Mad Dog's: Derby Party
  • Website
  • Don your best hat and turn out for the annual Kentucky Derby Party to benefit Upper Keys Humane Society at Ziggy & Mad Dog's, mile marker 83 bayside. The party, hosted by Captain Skip Bradeen, features the Best Hat and Dapper Dresser contests with fabulous prizes. A donation of $25 includes complimentary beer, wine and hors d'oeuvres.


  • May 05 - May 05 Key West
  • The Marker: Cinco de Mayo Margarita Battle
  • Website
  • Gather by the pool at The Marker, 200 William St., at 3 p.m. for the 2nd annual island-wide margarita battle. Bartenders from The Starboard Restaurant & Bar at The Marker, Southernmost Beach Cafe, The Gates Hotel and 24 North Hotel shake up their tastiest margaritas, and you get to be the judge. Live music by Les Greene and The Swayzees.


  • May 10 - May 11 Marathon
  • 18th Annual Mother's Day Dolphin Tournament
  • Website
  • Cash and prizes will be awarded for the heaviest fish and to anglers who finish second through fifth place in this popular, annual tournament. There are four categories for prizes: professional, weekend warrior, ladies, 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 at Marathon Yacht Club, 825 33rd St. Gulf. The event benefits Habitat for Humanity of the Middle Keys.

  • May 11 - May 11 Key West
  • Reef Relief Annual Luau Fundraiser
  • Website
  • Reef Relief holds its annual luau celebration from 5 to 8:30 p.m. at Lagerheads Beach Bar & Grill, located at 0 Simonton St. Enjoy live music from Gary Hempsey, games, a raffle, a silent auction and more.

  • May 12 - May 12 Key West
  • Tennessee Williams Theatre: One Night of Queen
  • Website
  • For over 20 years Gary Mullen and The Works have been performing their world-renowned "One Night of Queen" live concert. Gary Mullen & The Works will have you dancing in the aisles during their show, while the band pays tribute to the stage theatrics, showmanship, and music of Rock & Roll Hall of Fame inductees: Queen. Tickets $45 to $135. Show at 8 p.m. 5901 College Rd.

  • May 16 - May 16 Islamorada
  • 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. On the Third Thursday of each month, Keys-inspired fine artists, vendors, residents, and visitors congregate on Morada Way in Islamorada to celebrate the arts and culture in the Florida Keys. 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.

  • May 17 - May 19 Islamorada
  • ‘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 - May 18 Big Pine Key
  • King of the Reef Rod & Spear Tournament & Trash Cleanup
  • Website
  • This Lower Keys tournament has three divisions -- rod and reel, scuba and free diving. Competitors in each division compete for prizes for the largest black grouper and mutton snapper. The person catching the largest black grouper out of all three divisions is to be named the King of the Reef and grand prize winner. The catcher of the largest mutton snapper wins the mutton snapper calcutta. There is also a prize for the most polypropylene trash collected and weighed at the final tournament weigh-in. The tournament was established to raise awareness about diving decompression injuries and raise funds for victims. Tournament events, including the Saturday evening weigh-in and awards ceremony, are based at The Docks Stock Island, 6840 Front St.

  • May 18 - May 18 Key West
  • Reelin' For the Cause Kids Fishing Tournement
  • Website
  • The tournament raises awareness about congenital heart defects and provides funds to support families with infants born with these disorders. Check in at 9:30 a.m. at Edward B. Knight (White Street) Pier at 9:30 a.m. $15 per child. Rod, reel and bait provided. Lines in at 10 a.m.; awards ceremony at 11:45 a.m. Awards for biggest fish in each age group: 3 to 5; 6 to 8; and 9 to 13. Sharks will be their own category with one award for the largest shark across all age groups. There is also a silent auction at the pier during the tournament.

  • May 18 - May 18 Key Largo
  • Key Largo Critter Cruise
  • Website
  • Come by land or sea to participate in the Key Largo Critter Cruise to benefit the Upper Keys Humane Society. Captain up with teams of four per boat or car and cruise or crawl to a selection of favorite Key Largo establishments to compete in games and contests for spectacular prizes. Costumes are encouraged -- prizes will be awarded for best dressed boat and best dressed team. The event takes place from 10 a.m. to 4 p.m. Starts and ends at the Caribbean Club, mile marker 104 bayside.

  • May 18 - May 19 Key Largo
  • 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.

  • May 22 - May 22 Big Pine Key
  • Florida Keys Wildlife Society: Full Moon Kayak Excursion
  • Capt. Bill Keogh 305-872-7474 Website
  • This kayak excursion, sponsored by Captain Bill Keogh of Big Pine Kayak Adventures, takes place from 6:45 to 8:45 p.m. in the waters surrounding the National Key Deer Refuge in Big Pine Key. The trip begins at Old Wooden Bridge Marina, 1791 Bogie Road, and proceeds across the water to No Name Key and north. Call or text Captain Bill at 305-872-7474 to reserve your spot and your kayak and gear. Cost is $30, which is a donation to Florida Keys Wildlife Society.

  • May 26 - May 26 Key West
  • Schooner Wharf Bar: Minimal Regatta
  • Website
  • Watch sailors make a splash in homemade vessels made from plywood and duct tape in the craziest regatta you'll ever see on the waters of Key West Bight. Watch from the Historic Seaport walkways near Schooner Wharf. 12 noon at 202 William St.

  • May 31 - June 02 Key Largo
  • 10th Annual Skippers Dolphin Tournament
  • Email Website
  • This 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.

  • May 31 - June 01 Marathon
  • Marathon Community Theatre: tah-DANCE
  • Website
  • The 15th annual tah-DANCE Community Dance Showcase lets you experience the art of dance through performances by the MCT dance department, local community dance studios, dance groups and individual dancers during an evening of performances created to entertain and enthrall. Two shows - Friday and Saturday nights at 7 p.m. 5101 Overseas Hwy.

  • June 01 - June 01 Key West
  • Key West Theater: Pride Follies
  • Website
  • The Key West Business Guild opens this year’s PRIDE month with Pride Follies, showing at the Key West Theater, 512 Eaton St. Pride Follies began 17 years ago to give Key West performers who usually perform in bars and restaurants the chance to appear on the professional stage. 2017 Fantasy Fest Queen Destiny Montgomery again directs this year’s production filled with comedy, singing, and dancing. Doors open at 6 p.m.; show at 7 p.m.

  • June 03 - June 07 Key West
  • 50th Annual Don Hawley Invitational Tarpon Fly Tournament
  • Website
  • Formed in 1975 to honor fishing legend Don Hawley, this tournament awards the Grand Champion award to the angler and guide team with the most points accumulated over the five-day competition for tarpon caught on fly and released. Champions names are added to the perpetual trophy on display at Florida Keys Outfitters in Islamorada. Proceeds benefit the Guides Trust Foundation that supports Keys inshore fishing guides during times of need.

  • June 05 - June 09 Key West
  • Key West Pride
  • Website
  • Celebrate PRIDE on the tropical island of Key West that is legendary for its laid-back style and its open and accepting atmosphere. Whether you’re looking to party with friends, travel with family, or to get lost in the magic of the southernmost city, rediscover Key West and discover how the island has created one of the most integrated and unique communities in the world. Show us your pride, we will show you our Key West Pride!

  • June 07 - June 09 Big Pine Key
  • Lower Keys Chamber of Commerce Dolphin Tournament
  • Website
  • The Lower Keys Chamber of Commerce presents the 31st annual event where anglers contend for over $35,000 in cash prizes and awards. A special cash prize of $20,000 is awarded for the largest dolphin over 50 pounds -- this prize is available only to the anglers on the first 50 boats registered for the tournament. Additional prizes await winners in open, ladies and youth divisions.

  • June 07 - June 07 Key West
  • Coffee Butler Amphitheater: Billy Currington
  • Website
  • Well-known for his smooth and distinct voice and songs including "Don't Hurt Like it Used To" and "People Are Crazy," Billy Currington comes to the amphitheater with opener Mike Stack. Doors open at 6 p.m.; show at 7:30 p.m. 21 E. Quay Rd.

  • June 08 - June 08 Key West
  • CFK Swim Around Key West
  • Email Website
  • Embark on an adventurous competitive swim - a 12.5 loop around the island. The pristine waters around Key West give swimmers great views of both the land and underwater life. Compete in different categories including solo swimmer, solo swimmers with fins, solo swimmers using a mermaid tail or a monofin, or gather your friends and compete in the relay category of 2-person, 3-person, 4-person, 5-person or 6-person teams. Not interested in the full island swim? Try some of the smaller races offered, a 6.1-mile swim, a 2-mile swim, a 1-mile swim or an 800-yard swim. Swims begin and end at Higgs Beach, 1000 Atlantic Boulevard.

  • June 09 - June 09 Key West
  • Key West Pride Parade
  • Website
  • The Key West Pride Parade theme this year is "Celebrating the 70s Disco Era." The parade begins at 5 p.m. at the Quay at Truman Waterfront Park, traveling to Duval Street and ending at United Street.

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