Calendar of Events

May 2024: Florida Keys Events

Image for NAS Key West Southernmost Air Spectacular Image for NAS Key West Southernmost Air Spectacular Image for NAS Key West Southernmost Air Spectacular Image for NAS Key West Southernmost Air Spectacular
Image for 2nd Annual Key West Sailfish Tournament Image for 2nd Annual Key West Sailfish Tournament Image for 2nd Annual Key West Sailfish Tournament Image for 2nd Annual Key West Sailfish Tournament
Image for 18th Annual Nick Sheahan Dolphin Rodeo Image for 18th Annual Nick Sheahan Dolphin Rodeo Image for 18th Annual Nick Sheahan Dolphin Rodeo Image for 18th Annual Nick Sheahan Dolphin Rodeo
Image for Key West Art & Historical Society: Flora & Fauna - Early Naturalists in Florida
  • Mar 15, 2024 - Sep 13, 2024 Key West Arts & Culture
  • Key West Art & Historical Society: Flora & Fauna - Early Naturalists in Florida
  • Website
  • Enjoy the “Flora & Fauna: Early Naturalists in Florida” exhibit through September 13 at Key West Museum of Art & History's Custom House, Museum, 281 Front Street. The exhibit includes short biographies of the principal naturalists working in the Florida Territory in the early nineteenth century alongside representations of their Florida-inspired works. Their observation of plants and animals was an art as well as a science.
Image for Waterfront Playhouse: Lost in Yonkers
  • Apr 24, 2024 - May 11, 2024 Key West Arts & Culture
  • 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.
Image for Key West Tropical Forest & Botanical Garden: Art in the Garden
  • Apr 28, 2024 - Jul 31, 2024 Key West Arts & Culture
  • Key West Tropical Forest & Botanical Garden: Art in the Garden
  • Website
  • Emphasizing harmony with nature, the return of Art in the Garden showcases local art and sculptures with artistic expressions. Artworks are earth-friendly in the selection of materials and themes and include recycled, repurposed, and natural material. Meander over garden boardwalks and down pathways through dappled shade, colorful blossoms and winged creatures to spot many beautiful works of art. View daily through July 31. 5210 College Rd.
Image for The Gates Hotel: Rev Up -- Meet Up & Write
  • May 1, 2024 Key West Arts & Culture
  • The Gates Hotel: Rev Up -- Meet Up & Write
  • Website
  • The Gates Hotel hosts a special event Wednesday afternoon from 1 to 5 p.m. as part of the Key West Songwriters Festival. It's a meet-and-greet with songwriters, plus attendees will have a chance to help the songwriters create an original song for the event. Featured artists include the Andy Wescott Band, James Slater, Rob Snyder, Jobe Fortner and Ryan Nelson. Also in attendance will be members of CreatiVets, whose mission is to empower wounded veterans to heal through the arts and music. Free to attend. 3820 N. Roosevelt Blvd.
Image for Studios of Key West: First Thursday Open House
  • May 2, 2024 Key West Arts & Culture
  • 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.
Image for Coffee Butler Amphitheater: Cole Swindell
Image for The Studios of Key West: Gallery Talk with Artist Anthony Mancuso
Image for Angler & Ale: Rock the Dock Cinco de Mayo Celebration
Image for Key West Outdoor Movies: Pixar's UP
  • May 3, 2024 Key West Arts & Culture
  • 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.
Image for Ziggy & Mad Dog's: Derby Party
  • May 4, 2024 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.
Image for Talk Derby to Me
  • May 4, 2024 Key West Arts & Culture
  • 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.
Image for History of Diving Museum: Vintage Dive Weekend
  • May 4, 2024 Key Largo Environmental
  • 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.
Image for Florida Keys Aquarium Encounters: Mermaids
  • May 4, 2024 - May 5, 2024 Marathon Arts & Culture
  • 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.
Image for Schooner America 2.0: Starry Night Stargazing Sail
  • May 4, 2024 - May 5, 2024 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.
Image for Bob Traa Faro Blanco Tarpon Tournament
  • May 4, 2024 - May 11, 2024 Marathon Fishing
  • 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 captdonna1@aol.com.
Image for Cow Key Bridge Run: Cow Wars 2024 - May the 4th Be With Moo!
  • May 4, 2024 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.
Image for Schooner Wharf Bar: Cinco de Mayo
  • May 5, 2024 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.
Image for Run for Rhonda 5k
  • May 5, 2024 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.
Image for The Marker: Cinco de Mayo Margarita Battle
  • May 5, 2024 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.
Image for Sloppy Joe's 87th Anniversary at the Corner of Duval and Greene Streets
Image for Tropic Cinema: The Marching Conchs in London Premier
Image for John Pennekamp Coral Reef State Park: World Shrimp Day Discovery Table
Image for Key West Art & Historical Society Distinguished Speaker Series: Key West Ghost Stories with Wayne Garcia
Image for Bud N' Mary's Marina: Lionfish Derby Film & Shellfish Panel Discussion
Image for John Pennekamp Coral Reef State Park: World Migratory Bird Day Event
Image for Reef Relief Annual Luau Fundraiser
  • May 11, 2024 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.
Image for Sheriff's Animal Farm Open House
  • May 12, 2024 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.
Image for Tennessee Williams Theatre: One Night of Queen
  • May 12, 2024 Key West LGBTQ
  • 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.
Image for Tackle Box: Monthly Fishing Seminar -- Deep Drop Basic Rigs
Image for Matecumbe Historical Trust: "The Keys Worst Hurricanes"
  • May 14, 2024 Islamorada Arts & Culture
  • Matecumbe Historical Trust: "The Keys Worst Hurricanes"
  • 305-393-0940
  • A free presentation from the Irving R. Eyster collection will show the impacts of several Keys hurricanes, starting with the storm that hit the 1733 Spanish treasure fleet, the 1935 Labor Day hurricane, Hurricane Donna in 1960 and Hurricane Irma in 2017. These storms were some of the most destructive hurricanes in Florida Keys history, with the 1935 Hurricane being the strongest storm of the century. The presentation begins at 6 p.m. at Islamorada Public Library, mile marker 81.5 bayside.
Image for REEF Fish & Friends
  • May 14, 2024 Key Largo Environmental
  • REEF Fish & Friends
  • Website
  • This month's free Fish & Friends seminar provides information about how how snorkelers and divers can be empowered to support coral restoration. Speaker Maddie Cholnoky with Florida Keys National Marine Sanctuary explains how the dive industry and recreational divers and snorkelers play a crucial role in spreading awareness about marine conservation, and providing hands-on ways to help. The evening begins with a social gathering from 6:15 to 7 p.m. followed by the presentation. Meet at the REEF campus, 98300 Overseas Highway
Image for Florida Keys History & Discovery Center: Summer Palette Art Show
Image for History of Diving Museum Immerse Yourself Presentation: Salvaging the Deep with Dr. Joe Dituri
  • May 15, 2024 Islamorada Arts & Culture
  • 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.
Image for Mrs. Macs Kitchen: Tanteo Tequila Pairing Dinner
Image for Marathon Community Theatre: Mousetrap
  • May 16, 2024 - May 19, 2024 Marathon Arts & Culture
  • Marathon Community Theatre: Mousetrap
  • Website
  • The marvelous whodunit, Mousetrap wraps up its run at Marathon Community Theatre with performances Thursday through Saturday at 8 p.m. plus a 3 p.m. Sunday matinee May 19. This record-breaking, longest running murder mystery play features a brilliant surprise ending from Dame Agatha Christie, the foremost mystery writer of her time. Tickets $28. 5101 Overseas Highway.
Image for Morada Way Third Thursday Art Walk
  • May 16, 2024 Islamorada 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. 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.
Image for King of the Reef Rod & Spear Tournament & Trash Cleanup
  • May 17, 2024 - May 18, 2024 The Lower Keys Fishing
  • 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.
Image for Bayview Park: Law Enforcement Memorial Ceremony
Image for Shady Palm Art Gallery Anniversary Celebration
Image for History of Diving Museum: Salvaging the Deep
Image for Studios of Key West: Craig Foster Discusses His New Book, Amphibious Soul
  • May 17, 2024 Key West Arts & Culture
  • 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.
Image for Key Largo Critter Cruise
  • May 18, 2024 Key Largo
  • Key Largo Critter Cruise
  • Website
  • Teams will come by land or by sea to participate in the annual Key Largo Critter Cruise to benefit the Upper Keys Humane Society. Teams of four per boat or car are to 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. and starts and ends at the Caribbean Club, mile marker 104 bayside. If you're not participating, just come by the bar in the afternoon to watch the shenanigans.
Image for Windley Key Fossil Reef Geological State Park: Junior Ranger Jamboree
Image for Reelin' For the Cause Kids Fishing Tournement
  • May 18, 2024 Key West Fishing
  • 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. Registration is now full. For registered children, check in at 9:30 a.m. at Edward B. Knight (White Street) Pier. Rods, reels 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. Spectators may take part in the silent auction at the pier during the tournament.
Image for Florida Keys Wildlife Society: Full Moon Kayak Excursion
  • May 22, 2024 The Lower Keys Environmental
  • 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.
Image for Upper Keys Humane Society: Cat Yoga
  • May 22, 2024 Key Largo
  • Upper Keys Humane Society: Cat Yoga
  • Website
  • Enjoy a gentle yoga class along with cats and kittens in the Cat Cafe beginning at 6 p.m. at mile marker 101.6 oceanside. Bring your own mat. Register in advance. The $25 fee is a donation to Upper Keys Humane Society.
Image for John Pennekamp Coral Reef State Park: Mosquito Discovery Table
Image for John Pennekamp Coral Reef State Park: Sharks - Fact or Fiction Ranger Talk
Image for Village Square: Sizzling Summer Fashion Show
  • May 25, 2024 Islamorada
  • Village Square: Sizzling Summer Fashion Show
  • Website
  • The Village Square fashion show features the latest fashions from Miss Monroe, The Otherside, and the Mayu, Wild Lily and Evolve Boutiques. There will be music by DJ Chili, a cash bar with wine, beer and sangria, a fun photo booth and food available from Bad Boy Burrito. Gates open at 6:30 with the show at 7:30 p.m.
Image for Florida Keys Wild Bird Rehabilitation Center: Summer Movie Night Featuring "Hoot"
  • May 25, 2024 Key Largo Arts & Culture
  • Florida Keys Wild Bird Rehabilitation Center: Summer Movie Night Featuring "Hoot"
  • Website
  • Celebrate the start of Summer Movie Night at the Laura Quinn Wild Bird Sanctuary with a screening of "Hoot," a movie about kids who join together to save burrowing owls. The film is based on Carl Hiaasen's book of the same name, and features Jimmy Buffett in a cameo role as the high school science teacher. All ages are welcome. Drinks and popcorn are free, but donations for the birds are always welcome. Bring camp chairs and blankets for seating.
Image for Island Grill: Memorial Day Weekend Full Moon Beach Party
Image for Caribbean Club: Memorial Day Weekend BBQ to Benefit Disabled Veterans
Image for Sheriff’s Animal Farm Open House
  • May 26, 2024 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.
Image for Schooner Wharf Bar: Minimal Regatta
  • May 26, 2024 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.
Image for Gordon Ramsay: Uncharted
  • May 27, 2024 The Florida Keys Arts & Culture
  • Gordon Ramsay: Uncharted
  • The season premiere of "Gordon Ramsay: Uncharted" spotlights the fabulous Florida Keys. Follow along as the area's vibrant locals challenge him to embrace the Conch Republic's way of life. He traverses shimmering seas, gathering insider tips along the way, as he gets up close and personal with lobsters, crab and fish before facing off against daredevil chef and rum distiller Paul Menta as the final cook. "Gordon Ramsay: Uncharted" premieres on National Geographic May 27th at 9 p.m. ET (8 p.m. CT) and will be available to stream the next day on Disney+ and Hulu.
Image for Matecumbe Historical Trust: Memorial Day Service at Islamorada Hurricane Monument
Image for Wear Blue: Run to Remember in Key Largo
  • May 27, 2024 Key Largo
  • Wear Blue: Run to Remember in Key Largo
  • Website
  • Join with others to Wear Blue and Run to Remember the 65 thousand service members who have given their lives since the Vietnam War during the Hero March, taking place throughout Memorial Day Weekend across the country both live and virtually. A group event takes place in Key Largo Community Park, 500 St. Croix Place, from 8 to 9 a.m., with attendees take purposeful steps -- both walking and running -- as a living memorial to fallen warriors.
Image for Hale Gallery: Hot Summer Night Opening Reception
Image for Key West Art & Historical Society: Beaches, Creatures & Cowboys - Florida Movie Posters Opening
Image for Marathon Community Theatre: tah-DANCE
  • May 31, 2024 - Jun 1, 2024 Marathon Arts & Culture
  • 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.
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