Events in the Florida Keys

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

Events in Florida Keys for 2024

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  • 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 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 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 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 the World's Looooongest Parade down Duval St. Thursday, April 25 at 8 p.m.; the Naval Parade and Great Sea Battle Friday night on Key West Harbor starting at 7 p.m.; the Blue Ribbon Bed Races Saturday at 3 p.m., followed by the Brawl on Duval amateur boxing match starting at 7 p.m. and the Pirate Ball & Costume Contest at Schooner Wharf, also at 7 p.m. Saturday; and the Schooner Wharf Wrecker's Cup race series Sunday afternoon .

  • 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 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 28 Islamorada
  • Afro Roots Fest
  • Website
  • Audiences in Islamorada can enjoy three days of multicultural music with an all-star South Florida lineup of Afro Roots artists performing live Friday through Sunday in the beer garden at Florida Keys Brewing Company, 81611 Overseas Highway in the Morada Way Arts & Cultural District. The Friday 6 p.m. show features Jean P. Jam; on Saturday, the music starts at 6 p.m. with Venozonix, followed by Miami-based Cortadito; and starting at 2 p.m. Sunday, hear Manny Swagg and Stella Fusion.

  • April 27 - April 27 Key West
  • Conch Republic Independence Celebration: Pirates' Ball
  • Website
  • As part of the annual Conch Republic Independence Celebration, the Pirates' Ball is a night of swashbuckling fun and merriment. Watch the daring swashbuckling and sword fighting performance by the Conch Republic Privateers. Come in costume to win great prizes. The fun begins at 7 p.m.

  • April 27 - April 27 Key Largo
  • REEF Arts & Science Festival
  • Website
  • Dive into creativity at this family-friendly event featuring local artists and environmental organizations. The event aims to engage participants and show how the arts can connect everyone to science and conservation. Enjoy interactive displays, educational games and hands-on art activities. 10 a.m. to 3 p.m. at the REEF campus in the median at 98300 Overseas Highway.

  • April 27 - April 27 Key West
  • Key West Botanical Garden: Earth Day/Arbor Day Eco-Fair
  • Website
  • Celebrate both Earth Day and Arbor Day with an Eco-Fair at Key West Botanical Garden from on April 27. Activities include a docent-led tour of the garden at 10:30 a.m.; children's art activities from 10 a.m. to noon; a tour of the Key West Native Nursery at 11:30 a.m.; a composting demonstration at noon; a rain barrel workshop from 1 to 2 p.m.; a bicycle raffle at 1 p.m. and native plant sales from 10 a.m. to 2 p.m.

  • April 27 - April 27 Islamorada
  • The Nest at Green Turtle Comedy Show
  • Website
  • The Green Turtle's monthly comedy show features some of the best touring comedians from Florida and beyond. The show is hosted by Lando Gonzalez and features comedian Sheena Reagan with headliner Nathan Wallace. Two showtimes, at 6 and 8 p.m., with seatings at 5 and 7 p.m. Come early for dinner and drinks at The Nest, 81219 Overseas Hwy.

  • 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 and the Navy K-9 squad, 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 - 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 27 - May 01 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 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
  • 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
  • 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 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 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
  • Key West Outdoor Movies: Pixar's UP
  • Website
  • All are welcome to this free, family-friendly Key West Outdoor Movie Night featuring Pixar's "UP" on the lawn at Fort East Martello, 3501 S. Roosevelt Blvd. Doors open at 6:30 p.m. with the movie starting at dusk. Bring a blanket or a low-profile chair. Popcorn is free.

  • 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 04 - May 04 Key West
  • Talk Derby to Me
  • Website
  • Support the Key West Mounted Police Unit at the 7th annual "Talk Derby to Me" event at The Gardens Hotel, 526 Angela St. Dress up to compete in the best costume, best hat and best couple contests. Get photos with the Key West P.D. horses and officers, and enjoy mint juleps and food. $25 donation at the door.

  • May 04 - May 05 Marathon
  • Florida Keys Aquarium Encounters: Mermaids
  • Website
  • See live mermaids swimming the coral reef tank at Aquarium Encounters! Swim shows will be at 10 a.m. and 2 p.m. each day and are included with admission. After the swim show, you can have your own private meet and greet with the mermaids for photos for a $5 charge. Attendees can also book an encounter experience to get in the tank with the mermaids to join them in feeding the rays, fish and other creatures swimming in the tank. Sign up for encounters at the front desk. 11710 Overseas Highway.

  • May 04 - May 05 Key West
  • Schooner America 2.0: Starry Night Stargazing Sail
  • Website
  • Sail through Key West waters by starlight on this stargazing sailing adventure aboard the 105-foot Schooner America 2.0, featuring live narration from NASA Solar System Ambassador and Key West resident, Kevin Gallagher. Trip departs at 9:15 p.m. from the dock at Key West Bight, 202 William St.

  • May 04 - May 04 Key Largo
  • History of Diving Museum: Vintage Dive Weekend
  • Website
  • Participants will have the opportunity to use authentic double-hose regulators like the ones used on "Sea Hunt" and by Jacques Cousteau. Saturday dives at Jules Undersea Lodge, 51 Shoreland Dr., will take place every hour from 10 a.m to 3 p.m. There will be demonstrations of Mark V dive dress for use at deep dive depths at 11:30 a.m. and 1 p.m. On Sunday, there is an afternoon reef dive with Silent World Dive Center. Information and sign-up for vintage dives available online.

  • 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 05 - May 05 Key West
  • Sloppy Joe's 87th Anniversary at the Corner of Duval and Greene Streets
  • Website
  • The iconic Sloppy Joe's Bar celebrates 87 years at its current located at the corner of Duval and Greene Streets on May 5. It was previously located in the building that is now Captain Tony's. If you're in Key West, but sure to stop by for a cocktail, and if not, you can check out the Sloppy Joe's Bar Cam.

  • May 05 - May 05 Key West
  • Schooner Wharf Bar: Cinco de Mayo
  • Website
  • Schooner Wharf Bar's 25th annual Cinco de Mayo celebration takes place from 7 p.m. until midnight. Win a prize for the best Mexican hat, compete in the Super Hot Taco Eating Contest for prizes, and party with live music by the Cool Coconuts Band. 202 William St.

  • 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 05 - May 05 Key West
  • Run for Rhonda 5k
  • Website
  • Run or walk your way through Key West on Cinco de Mayo for the first annual Run for Rhonda. Starting and finishing at Truman Waterfront Park, the race will be followed by a fabulous post-race party with DJ Jimmy Jam, adult and non-alcoholic beverages, festive food, a raffle and more. The run honors the legacy of Key West resident Rhonda Flores and supports a college scholarship for a participant in the Take Stock in Children program.


  • 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
  • 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.

  • 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 15 - May 15 Islamorada
  • History of Diving Museum Immerse Yourself Presentation: Salvaging the Deep with Dr. Joe Dituri
  • Website
  • Retired Navy Commander Joe Dituri served continuously in active service upon various ships and stations where he was involved in every aspect of diving and special operations work, from saturation diving and deep submergence, to submersible design and clearance diving. Join Joe, who is well-known for setting the new underwater habitation record in 2023 at Jules Undersea Lodge, as he discusses salvage operations conducted during his incredible career. The presentation kicks off the museum's new featured exhibit, Salvaging the Deep. Attendees will be able to see the exhibit for its grand opening. 7 p.m. at the museum, located at mile marker 82.9 bayside.

  • 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 17 - May 17 Key West
  • Studios of Key West: Craig Foster Discusses His New Book, Amphibious Soul
  • Website
  • From the creator of the beloved Academy Award winning documentary “My Octopus Teacher” comes "Amphibious Soul," Craig Foster’s thrilling memoir of a life spent exploring the most incredible places on Earth – from the Great African Seaforest to the crocodile lairs of the Okavango Delta. Foster reveals how we can attend to the earthly beauty around us and deepen our love for all living things, whether we make our homes in the country, the city, or anywhere in between. $40 ticket includes a copy of the book. Doors open at 6 p.m., talk at 7 p.m.

  • 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 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 19 Key West
  • 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 26 - May 26 Key West
  • 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.

  • 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.

  • 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.

  • 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 15 Key West
  • REEF Fish Out of Water Virtual 5k
  • Website
  • The fifth annual REEF Fish Out of Water Virtual 5k is an incentive to get active and support Florida Keys marine conservation and education. Sign up and join one of five Fish Teams: pygmy seahorse, lumpfish, saddled butterflyfish, horn shark or fairy basslet. You can also sign up as a "Fish Shoal" group. You can choose to run, walk, hike, bike or swim the 5k (3-point-1 miles) all at once or break into smaller sections. Registered participants receive a limited edition race shirt, printable race bib and a set of fish team stickers.

  • June 08 - June 08 Key West
  • Big Gay 5k
  • Website
  • The second annual Big Gay 5k race takes place on Saturday, June 8 during Key West Pride. The start and finish line is the famous Rainbow Crosswalk on Duval Street. The race starts at 8 a.m. and is to be followed by "The World's Most Fabulous Post-Race Party" at 22 & Company, 504 Angela St., which will include awards for Most Spirited, Best Hair, Hottest Socks and more. Register in advance at RunSignUp.com.

  • 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
  • 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.

  • 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.

  • June 14 - June 15 Marathon
  • Father's Day Dolphin Derby
  • Website
  • This popular dolphin tournament with check-in on Friday and fishing Saturday pays out over 8 thousand in cash and prizes to the top four adults with the heaviest fish. Junior anglers age 15 and under vie for rod and reel combos.

  • June 15 - June 15 Marathon
  • Key West Theater: John Hiatt
  • Website
  • Songwriting genius John Hiatt performs at Key West Theater June 15 at 8 p.m. Tickets start at $120. 512 Eaton St.

  • June 15 - June 15 Key West
  • Harry S. Truman Little White House: Truman's Tropical Fruit Festival
  • Website
  • Can you tell the difference between a haden and a kent mango? At the Tropical Fruit Festival, you’ll have the chance to taste all types of mangoes and other tropical fruits, sip tasty cocktails, watch cooking demos, purchase tropical trees, shop with local vendors and more. 9 a.m. to noon. 111 Front St.

  • June 20 - June 22 Islamorada
  • University of Miami Sports Hall of Fame & Museum Celebrity Fishing Tournament
  • Website
  • Anglers are invited to join celebrities to fish for the highest aggregate weight of 3 dolphin fish (mahi-mahi) and other species in this fundraiser for charities including the Buoniconti Fund to Cure Paralysis, Habitat for Humanity of the Upper Keys, the Coastal Conservation Association, the Ari Arteaga Foundation, and the UM Sports Hall of Fame & Museum. Tournament events take place at Postcard Inn & Marina, mile marker 84 oceanside.

  • June 20 - June 20 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.

  • June 23 - June 23 Key West
  • 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.

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