The Lodging Association of the Florida Keys and Key West

Keys Events

Florida Keys & Key West Events Information, Accommodations of the Florida Keys. Plan your Island vacation around an event or holiday.
Events calendar provided by www.fla-keys.com.

Events in the Florida Keys for May, 2022
Year: Month:  
April 16 to May 21,  in Key West
Key West Tropical Forest & Botanical Garden Speaker Series
Interested in learning more about the complex and fascinating environmental world of Key West and the Florida Keys? Then join a Speaker Series the third Saturday of each month this spring. Topics include April 16: ‘The Cuban Chugs’ with Dr. John Bratten, University of West Florida; and May 21: ‘Biodiversity and Butterflies’ with Taylor Hun, US Fish & Wildlife Field Technician. Lectures are held in the Nature Chapel at Key West Tropical Forest & Botanical Garden is located at 5210 College Rd., on Stock Island. Free for members, $10 for non-members.


April 29 to May 01,  in Key West
Red Barn Theatre presents: How To Eat Like a Child and Other Lessons in Not Being a Grownup
Starring a host of Key West's finest young and playful actors, the show is based on a book by Nora Ephron, who also wrote the play, along with music and lyrics by John Forster. It's a hilarious romp through the joys and sorrows of being a child, and will touch the child inside everyone in the theater. The show’s wonderful child actors give 23 lessons in subjects like how to beg for a dog, how to torture your sister, how to act after being sent to your room and how to laugh hysterically. But it's a limited run, so make sure you get your tickets early! Theatre is located at the rear of 319 Duval St.


April 29 to May 01,  in Marathon
Marathon Offshore Bull and Cow Dolphin Tournament
A grand prize of up to $10,000 cash is to go to the team that catches the largest bull and cow dolphin fish combined. Cash prizes for second- and third-place as well. Other prizes are awarded to anglers catching the largest dolphin, wahoo, tuna and tripletail.
Contact: Jack Carlson 305-481-0495
Email: [email protected]

May 01 to May 04,  in 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.
Contact: 215-542-1492
Email: [email protected]

May 04 to May 08,  in Key West
26th Annual Key West Songwriters Festival
Since 1997, BMI has been a presenting sponsor of the festival, one of the largest festivals of its kind in the world, and has helped it grow into both a tourist attraction and favorite of island locals. The festival revolves around five days and nights where live music bliss introduces crowds to the faces, voices and stories behind the songs.


May 06 to May 08,  in Islamorada
Nick Sheahan Dolphin Rodeo
Fishing for a cause! Honoring the memory of Nick Sheahan, a Florida Keys student, this tournament benefits a namesake community scholarship fund that has distributed over $315,000 to date. Hosted at Tavernier Creek Marina, the event features cash prizes and $25,000 to the angler with a dolphin fish that beats the state record.
Email: [email protected]

May 06 to May 07,  in Marathon
16th Annual Mothers Day Dolphin Tournament
Fish for a cause! Join this festive one-day fun fishing tournament for the heaviest mahi mahi. The entire event is a fundraiser to help Habitat Middle Keys build 11 additional affordable homes in Marathon. This angler tournament includes four prize categories: Professional, Weekend Warrior, Ladies Only and Jr. Angler (16 and younger). Registration fee is a donation is $175 per weekend warrior and pro anglers; $100 per lady angler and $75 per junior angler.


May 08,  in Key West
Comedy Key West presents: Gold Coast Comedy All-Stars
South Florida's Finest come to Comedy Key West for one night only! Three acts are to be featured: headliner Nik Macik, Chris Shepard and Dan Caso, each to present their own unique punchlines and life absurdities. Show starts 8:30 p.m., Comedy Key West is located at 218 Whitehead St.


May 12 to May 15,  in Key West
Comedy Key West presents: Rob Ross
Hosted by Tom Dustin (Comedy Central, Winner of the Great Canadian Laugh-Off), Comedy Key West presents Rob Ross who is to be performing with Key West local comedians. Rob Ross is a sought-after Canadian headlining stand-up comic and accomplished award winning television writer based in Toronto. Show starts 8:30 p.m. at Comedy Key West, 218 Whitehead St.


May 14,  in Big Pine
Stock Island Art Stroll
Experience Stock Island's unique art scene and creative culture, tour Stock Island's best art studios from 11a.m. - 5 p.m. Each location offers a variety of eclectic shops and working studios with multiple artists and disciplines from sculptures to woodworking, mosaics to screen printing, soaps to fabric art.


May 16 to May 19,  in Marathon
35th Annual Faro Blanco Invitational Tarpon Tournament
This unique team tournament in the heart of tarpon season, with two to four anglers per team/boat, allows anglers to fish three of the four 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
Email: [email protected]

May 16,  in Islamorada
Matecumbe Historical Trust presents: Early Mapping of the Florida Keys
Guest speaker, author and map researcher is Brian C. Schmitt. Presentation is free and open to the public. Starts at 6:30 p.m., Island Community Church, mile marker 82 in Islamorada.
Contact: Barbara Edgar 305-393-0940


May 17,  in Islamorada
Matecumbe Historical Trust Taste of History Dining Event
Enjoy a delicious historical journey of Keys life. Learn about the history of the main ingredient in each dish, offering a modern twist to historical recipes. Guests must RSVP; cost is $69.99 per person, includes tax and gratuity. Doors open 6 p.m., at Old Conch Harbor in The Chart Room, 90311 Overseas Highway in Tavernier. Courses include lobster bisque, conch fritters, shrimp cocktail salad, fried coconut Shrimp, parmesan-crusted mahi mahi and Key Lime pie, each created from traditional Florida Keys recipes.
Contact: RSVP at 305-393-0940


May 17,  in Key Largo
Celebrating the Spiegel Grove at 20: A Saga Too Strange Even for Hollywood!
The public can enjoy a multimedia presentation and panel discussion with members of the initial “sink team” chronicling the intriguing history of Spiegel Grove, a retired 510-foot Navy Landing Ship Dock, intentionally scuttled on May 17, 2002, as an artificial reef. The free-admission event is slated for 7-9 p.m. in the auditorium of Key Largo’s Murray Nelson Governmental and Cultural Center, mile marker 102. Refreshments and beverages are to be served. Interested participants are asked to register with the Key Largo Chamber of Commerce.


May 19,  in Islamorada
Third Thursday Morada Way Art Walk
Enjoy a relaxing evening from 6-9 p.m. perusing local fine art, imbibing local craft beer and wine, listening to music, and seeing your favorite people! MWACD is a non-profit in the heart of Islamorada, between mile markers 81 and 82, with Morada Way Clay, Jessica Ann Art, Rum Brush, Limelight Studio/Gallery and other partners! Check out Art Walk the third Thursday of each month.


May 20,  in Key West
Reef Relief Luau Fundraiser
Rescheduled due to weather, Reef Relief invites the public for a night of live music, games and a silent auction. From 5-8 p.m., Lagerheads Beach Bar and Watersports, at 0 Simonton St. Reef Relief is a nonprofit membership organization dedicated to improving and protecting the coral reef ecosystem.


May 28 to May 29,  in Islamorada
Afro Roots Festival
Audiences can celebrate world music in the Florida Keys. Saturday evening’s show, beginning at 6 p.m. at the popular Florida Keys Brewing Co., mile marker 81, , is to spotlight the Caribbean-influenced world beat mastery of Johnny Dread, paired with the Latin-infused rhythms of Javier García. Sunday’s musical schedule begins at 4 p.m. Audiences can sway to the sounds of the nine-piece Latin funk band Suenalo, a critically acclaimed South Florida favorite, and the funky New Orleans style of the Bad Apples Brass Band. Both shows are to take place in the beer garden and admission is free.


May 30,  in Islamorada
Memorial Day Service
Ceremony will begin at 9 a.m. at the hurricane monument at mile marker 81.5. Barbara Edgar, President of the Matecumbe Historical Trust, is to make the introductory welcome presentation followed by the invocation, the Presentation of Colors, the National Anthem and guest speakers The service is open to the public. Residents and visitors are encouraged to attend in observance of Memorial Day.
Contact: Barbara Edgar 305-393-0940




The Lodging Association of the Florida Keys and Key West
818 White St.
Suite 8
Key West, FL 33040
  305-296-4959 phone
305-296-1408 fax
[email protected]

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