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.
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Events in the Florida Keys for May, 2023
Year: Month:  
January 13 to May 21,  in Key West
Key West Art & Historical Society: Bahama Village - Relics of a Fading Community
Bahama Village, in the westernmost portion of the city, was a neighborhood comprised of Black Bahamians and Black Cubans, Chinese, and other groups of color since the 1800s. In this exhibition, their history and stories are woven together through various events that shaped the Black and Indigenous cultures of Key West. “Bahama Village: Relics of a Fading Community" contains never-before-on-view objects that tell the inspiring history, culture and contributions of the island’s Black residents. Located at the society's Custom House Museum, 281 Front Street.

April 21 to May 05,  in Key West
Connections Project: Mural on Display in Key West
The Florida Keys Council of the Arts' Connections Project mural road show is underway, and this location is its final stop. This year's mosaic of 300 small paintings by Keys artists celebrates the Keys' unique history and bicentennial with the theme "Pirates to Pineapples in Paradise - 200 Years in Monroe County." The mural will be on display at the Florida Keys Council of the Arts headquarters at the historic Gato Building in Key West through May 5. 1100 Simonton Street.

April 27 to May 13,  in Marathon
Marathon Community Theatre: Scapino!
An Italian menu – think minestrone, macaroni, ravioli - sung to a snappy tune opens SCAPINO!, a fun-filled adaptation of Moliere's ''Les Fourberies de Scapin." Set in contemporary Naples, Italy, the leading character, Scapino, devises a complex plot to help two pairs of lovers against parental opposition that, it turns out, does not even exist. Scapino, a fast-talking, quick-thinking scamp cleverly manipulates and cajoles everyone around him into doing what he intends them to do. Slap-stick, over-the-top hilarity ensues in this uniquely musical farce. Shows at 8 p.m. except for a Sunday matinee on May 7 at 3 p.m. Tickets $28, available online. 5101 Overseas Highway, oceanside.

April 29 to May 06,  in Marathon
36th 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 Bridge. Proceeds from the charity tournament benefit Ronald McDonald House. Tournament activities take place at Faro Blanco Resort, 1996 Overseas Hwy. bayside.
Contact: Donna Vankirk
Email: [email protected]

May 01,  in Islamorada
Jeff Leonia Reel and Steel Classic
This fishing and diving event is for Grouper and Hogfish. Hosted at Angler House Marina. Prizes for 1st through 3rd place on rod and reel, freediving, and scuba. Contact Janice Driver, 919-414-4300 or register online.
Contact: Janice Drimer
Email: [email protected]

May 04,  in Key West
Keys Concerts By Candlelight: May the 4th Be With You
Keys Concerts by Candlelight presents “May the Fourth Be With You.” The unique concert experience features the music of Star Wars composer John Williams played by string quartet, and is led by the Southernmost Chamber Music Society member and violinist, Irie Monte. Hosted by comedian Steve Crane, the evening also features special guest appearances by the Sunshine State Stormtroopers. Doors open at 7, concert at 8 p.m. Tennessee Williams Theatre Cabaret, 5901 College Rd.

May 05,  in Islamorada
Full Moon Yoga with Coral Restoration Foundation
Relax and meditate during a yoga practice centered around how the moon affects our coral reefs, triggering coral spawning and the start of a new life for one of our planet's most precious ecosystems. Class takes place 7:30 to 8:30 p.m.on the deck at Postcard Inn, Islamorada, located at mile marker 84. $25 for non-guests of the resort.

May 05 to May 07,  in Marathon
Marathon Offshore Bull and Cow Dolphin Tournament
Up to $25,000 in cash and prizes awaits the top anglers who catch the largest bull and cow dolphin fish combined, while other prizes are awarded to anglers catching the largest dolphin, 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 05 to May 07,  in Islamorada
Nick Sheahan Dolphin Rodeo
Honoring the memory of Nick Sheahan, a Florida Keys student, this tournament benefits a namesake community scholarship fund that has distributed over $360,000 to date. The event features cash prizes for the top three adult anglers with the heaviest dolphin fish, and $25,000 to the angler with a dolphin fish that beats the state record. Walk-up registration is available until 9 p.m. at the Friday night cookout and captains meeting at Tavernier Creek Marina, mile marker 90.8.

May 06 to May 10,  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. 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.
Email: [email protected]

May 06,  in Key West
Shakedown on the Green -- Key West Island Market
All are welcome the first Saturday of every month for Shakedown on the Green: Key West Island Market, located on the Sunset Green Lawn at 24 North Hotel, 3820 N. Roosevelt. This family-friendly, Key West Island Market features local goods, artists, food trucks and more. Free admission and free parking. $5 mimosas available.

May 07,  in Key Largo
Key Largo Triathlon
This event features an Olympic and Sprint distance Triathlon and Duathlon, as well as an Olympic distance Aquabike race. The swim takes place in the water off Cannon Beach at John Pennekamp Coral Reef State Park; the bike will be out and back on Overseas Highway and Card Sound Road. The run portions takes participants through a lovely, laid-back Florida Keys neighborhood. Motorists are advised that one northbound lane on U.S.1 from mile marker 102.5 (the entrance to Pennekamp) to mile marker 105 will be coned off for cyclists’ use between 6:30 and 9:30 a.m. Sunday. The other northbound lane will remain open to vehicular traffic. This is the first of two 2023 Key Largo Triathlons; the second one takes place August 20th.

May 10,  in Islamorada
Florida Keys History & Discovery Center Lecture: Dr. Corey Malcolm - Monroe 200, the Bicentennial
Dr. Corey Malcolm is the Lead Historian for the Florida Keys History Center. Dr. Malcom specialized in researching the maritime past of the Florida Keys and the Bahamas. His lecture highlights the fascinating 200-year history of Monroe County. Doors open at 5 p.m. with light appetizers and a cash bar. Please register in advance. Tickets $10 in-person, $5 virtual. Mile Marker 82 at the Islander Resort.

May 10,  in Key West
USS HIGBEE Community Concert with Howard Livingston
Join Navy League Key West Chapter as they host a Community Concert at Coffee Butler Amphitheater to welcome the crew of the USS Lenah Sutcliffe HIGBEE DDG123 to Key West. The concert features a lineup of acclaimed musicians including country artist Cliff Cody, American Idol singer-songwriter Kristen McNamara, and headliner Howard Livingston and the Mile Marker 24 Band. This is your opportunity to meet the HIGBEE crew before the ship is commissioned on May 13. Tickets $10 available online. Active military free, as are children under 12. Food and drinks available for purchase - no outside coolers. Doors open at 4 p.m. 21 Quay Road.

May 11,  in Key Largo
Fish I.D. Class with REEF
Learn about the fantastic fish that you can see while exploring the underwater portions of John Pennekamp Coral Reef State Park. Experts from REEF Environmental Education Foundation will hold a fish identification class at 11 a.m. inside the Visitor Center and Aquarium. Class is free with regular park entry. Mile marker 102 oceanside.

May 11 to May 13,  in Islamorada
I.Care Trash Derby
To help reduce the amount of debris impacting the Keys, I.CARE is hosting its inaugural Trash Derby, sponsored by National Marine Sanctuary Foundation in support of clean seas. Register to team with a private dive operator or form your own team for either private boat or land-based divisions. The derby starts Thursday evening with a captains meeting at Bud & Mary's Marina, mile market 79.8. at 6:15 p.m. Trash collection takes place on land and sea from Key Largo to Big Pine Key all day Friday and half the day Saturday, followed by a family-friendly public festival at Founders Park (mile marker 87) on Saturday from 1 to 8 p.m. The festival is open to the public and includes food, music, games, an award ceremony, raffles, silent auction, environmentally-minded vendors, and local organizations working to improve our reefs.

May 12 to May 13,  in Marathon
17th Annual Mother's Day Dolphin Tournament
A combined total of $8,000 in cash and prizes will be awarded for the heaviest fish and to anglers who finish second through fifth place in this popular, annual one-day tournament. There are four categories for prizes: professional, weekend warrior, ladies, and junior angler. The event benefits Habitat for Humanity of the Middle Keys.

May 12,  in Key Largo
Kona Kai Resort & Gallery: Artist Taylor Hale Reception
Kona Kai Resort and Gallery invites you and your guests to attend a reception to shine a light on Key Largo artist Taylor Hale, known for his stunning artistic representations of the interactions between the sky, clouds and water in the Florida Keys. Hale's "A Colorful World" exhibit is currently on display at the resort's gallery. Enjoy hors d'oeuvres, refreshments and giveaways from 5 to 7 p.m., mile marker 97.8 bayside. Free to attend, RSVP requested (click website link).

May 13,  in Key West
Commissioning of USS Lenah Sutcliffe Higbee (DDG 123)
The USS Lenah Sutcliff Higbee (DDG-123) is to be commissioned in Key West Harbor during a ceremony from 10 a.m. to noon on Saturday, May 13. Tickets to the commissioning event are no longer available, but the event will be live-streamed at the website link in this event listing. The ship is the Navy’s 36th Arleigh Burke class Guided-Missile Destroyer.

May 13,  in Marathon
Wyland Repaints Murals at Crane Point Hammock
Join world-renowned muralist and fine artist Wyland, along with local artist and educator Shannon P. Wiley, as they recreate murals at Crane Point Hammock. Special admission price of $10 for adults and children get in free. Free food and drinks will be available. 11 a.m. to 5 p.m. 5550 Overseas Highway.

May 13,  in Key Largo
World Migratory Bird Day Programs at John Pennekamp State Park
Celebrate World Migratory Bird Day Saturday with guided bird count walks departing the park's Visitor Center & Aquarium at 9 a.m. At noon, there is a presentation on the Birds of Pennekamp at the Visitor Center. Programs are free with regular park admission. Register online. The park is located at MM 102.5 oceanside.

May 14,  in Key West
Sunset Green: Na Ma Sit & Stay Yoga with Your Dog
The Keys Collection offers Na Ma Sit & Stay Yoga with Your Dog the second Sunday of each month at 9:30 am. at the Sunset Green event lawn in Key West. Admission is free but a $10 donation is suggested, with all proceeds donated to Florida Keys SPCA. Bring your dog and your own mat. Located at 3820 N. Roosevelt Blvd. between The Gates and 24 North hotels.

May 15,  in Key West
Schooner Wharf Bar: Celebrating 26 Years of Magic!
Schooner Wharf celebrates 26 years of their very own Comedy Magic Bar featuring magician Frank Everhart. Frank will be on hand with a collection of special guests with magic, stories, and songs up their sleeves to commemorate another wonderful year of legendary Magical entertainment. The magical fun and live music from The Newton's Toko Irie starts at 7 p.m. 202 William Street.

May 17,  in Islamorada
History of Diving Museum: Immerse Yourself - Aquanauts to Astronauts
With nearly 30 years at NASA supporting human space flight and over 43 days spent in space, Dr. Michael Gernhardt is a seasoned astronaut and expert engineer. He led the installation of the International Space Station's airlock and helped to pioneer breathing techniques to combat decompression sickness risk in space. In addition to his NASA career, Gernhardt was a professional deepsea oilfield diver and founder of Oceaneering Space Systems. The Museum will also be unveiling our new exhibit all about the fascinating connection between spaceflight and diving; Aquanauts to Astronauts! Exhibit Preview the new exhibit from 5:30-6:45 p.m.; Immerse Yourself presentation begins at 7 p.m. The museum is located at 82990 Overseas Highway bayside. Register online for either in-person or Zoom.

May 18,  in Islamorada
Morada Way Third Thursday Art Walk in Islamorada
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 19 to May 21,  in Islamorada
Afro Roots Fest - Islamorada
Three days of music and fun with an all-star lineup of Afro Roots artists takes place on the stage at Florida Keys Brewing Company, 81611 Old Highway. On Friday at 6 p.m., the Miami-based power quartet Electric Kif opens the three-day event. Saturday at 6 p.m., enjoy the Cuban stylings of Cortadito and the Afro-Brazilian rhythms of Miamibloco. On Sunday, jam to the Nag Champions, Johnny Dread and Group Barrio Abajo beginning at 2 p.m. All three shows take place in the beer garden and admission is free.

May 19 to May 21,  in Islamorada
‘Ladies Let’s Go Fishing’ Screamin’ Reels Tournament
Intended for novice anglers, this weekend is about learning and a nonintimidating, fun competition with the “Ladies Let’s Go Fishing” university organizers. Participants can charter a professional 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 19,  in Marathon
Monroe County Bicentennial Celebration on Old Seven Mile Bridge
A commemorative celebration of the bicentennial of the founding of Monroe County commences at 6 p.m. on the Old Seven Mile Bridge. Attractions are to include live music and dancing, local artists painting on-site, catered tidbits by the Marathon High School culinary class and a sunset toast with vodka distilled from breadfruit grown at the Lower Keys’ Grimal Grove. Past and present commissioners who helped guide Monroe County are to be honored during the evening. Attendees can park at Marathon’s 7 Mile Marina property, 1090 Overseas Highway, with trolley service to the bridge provided by the Pigeon Key Foundation.

May 20 to December 31,  in Islamorada
History of Diving Museum: Aquanauts to Astronauts Exhibit
The Aquanauts to Astronauts exhibit focuses on the fascinating relationship between diving and space travel, how NASA uses diving to train future astronauts, and the incredible people who have both been to space and visited the bottom of the sea. The exhibit includes artifacts from NASA. The museum is located at 82990 Overseas Highway bayside.

May 20,  in Key West
Key West Art & Historical Society: Remember the USS Maine 125th Anniversary
In this Distinguished Speaker Series program, KWAHS's Dr. Cori Convertito presents a commemorative program on the 125th anniversary of the sinking of the USS Maine in Havana Harbor. The cause of the massive explosion that killed most of her crew in 1828 has never been definitively resolved, but it was a precipitating cause of the Spanish-American War that began shortly thereafter. Her talk will reveal surprising results of her own research into the destruction of the USS Maine. The presentation takes place from 6 to 7 p.m. at Tropic Cinema, 416 Eaton St. Tickets $15.

May 20,  in Key West
End of the Road 5k to Benefit Reef Relief
Start & finish your 5k run or walk Saturday morning at 8 a.m. at Key West's most iconic landmark, Mile Marker 0, and follow a route through Truman Waterfront Park, past the Southernmost Point Buoy Marker, Key West Lighthouse, the Hemingway Home & other favorite visitor destinations. Each participant receives a Mile Marker 0 bottle opener medal and sticker, along with a free beer or Bloody Mary while enjoying live music at the post race party at Mary Ellen's Bar, 420 Appelrouth Lane. Proceeds benefit Reef Relief. Register online at RunSignUp. $39 for runners and walkers.

May 20,  in Key West
Key West Tropical Forest & Botanical Garden: Speaker Series
Speaker John Bratton, professor of anthropology at University of West Florida, presents a program titled "Hope and Resolve" about the garden's Cuban Chug exhibit, a collection of homemade migrant boats telling a visual story of desperate migrants seeking freedom. He will also discuss artifact conservation and maritime archaeology tracking the decades of relations between the Florida Keys and Cuba, and the Cubans who helped build Key West over the past 200 years. The talk begins at 1 p.m. at the garden, 5210 College Rd. $10 per person; free for garden members.

May 20,  in Islamorada
History of Diving Museum: Opening of Aquanauts to Astronauts Exhibit with Special Guest
Meet Sydney Hamilton, aerospace engineer, commercial astronaut, and mathematician. She will speak on her aquanaut experience during Marine Resources Development Foundation's Project Neptune 100 undersea meeting with Dr. Joe Dituri and how it relates to her astronaut training. Hamilton promotes future careers in the fields of Science, Technology, Engineering, and Math (STEM) for young women and underrepresented youth. 3:30 to 4:30 p.m., 82990 Overseas Highway. Adults $15; kids 6-11 $7; kids under 5 free. Active military and their families free as part of Blue Star Museums.

May 20,  in Key West
Key West Business Guild: Pride Follies
The Key West Business Guild presents Pride Follies, a fun evening of the best and worst of local Key West entertainment, hosted by the former Queen of Fantasy Fest, Destiny Montgomery. Doors open at 7 p.m. and show starts at 8 p.m. at Key West Theater, 512 Eaton Street. Tickets $15 to $35.

May 20 to May 27,  in Key West
Waterfront Playhouse: Arsenic & Old Lace
The Award-winning Waterfront Playhouse brings the hilarious comedy classic Arsenic and Old Lace to the stage nightly through Saturday. Performance at 8 p.m., 407 Wall Street at Mallory Square.

May 21,  in Key West
The Studios of Key West: Tangos to Tarantellas
The Music Room presents Tangos to Tarantellas, an annual children’s welfare fundraiser showcasing the best classical musicians in the Keys. The twist? They’re all under 18 years old. Join musical director Robin Kaplan and her students for “a happy hour soiree” of classical dance music while enjoying refreshments and delectable bites. Helmerich Theater, tickets free at the door. Show starts at 5 p.m. 533 Eaton St., Key West.

May 21,  in Key West
10th Annual Running of the Chihuahuas
The smallest dogs with the biggest personalities are invited to enter the Chihuahua Races and win prizes along with bragging rights. Come to Rick’s Bar, 202 Duval Street on Sunday to see all the fun. Doors open at 1 p.m.; races start at 2 p.m. There are three categories of races -- Chihuahua pure and mixed breeds; senior pups; and all other small dogs. Preregister or show up on Sunday, $25 per dog. Spectators are free. Proceeds benefit Florida Keys SPCA.

May 26 to May 27,  in Key West
NAS Key West 27th Annual Dolphin Derby Fishing Tournament
The tournament kicks off Friday evening with a captains meeting and final registration at 6 p.m. at Sunset Lounge at Sigsbee Park, 911 Sigsbee Rd. (open to military patrons). Fishing takes place Saturday beginning at sunrise. Open to anglers with a valid military issued ID card and their guests. Only one military ID card holder is required per boat. Cash prizes for 1st through 3rd place.

May 28,  in Key West
Key West Artisan Market: Summer Edition
Stop by for brunch, shopping, fresh produce, baked goods and other foods to fill your pantry, and meet local artists. Full bar with great bloody Mary's and mimosas, too. The market's summer edition takes place every other Sunday from 10 a.m. to 2 p.m. at Key West VFW Post 3911, located at 2200 N. Roosevelt Boulevard.

May 28,  in Key West
Reggae Rehab Sunday Pool Party
The Reggae Rehab pool party is open to the public from 1 to 4 p.m. Sunday at The Marker Key West Harbor Resort. Music from Reggae Lou, drink specials, delicious barbecue and more.

May 28,  in Key West
Schooner Wharf Minimal Regatta
To compete in the wacky challenge, each six-member team must construct a craft out of the most minimal supplies: a single sheet of 4-by-8-foot plywood, two 8-foot-long 2-by-4s, a pound of fasteners and a trusty roll of duct tape. Regatta rules even forbid the use of caulking or adhesives, though epoxy paint is permitted. The "sink or swim" challenge is a Memorial Day Weekend tradition in the Florida Keys, with Sunday's fun scheduled to begin at 11 a.m. when teams can register at the Schooner Wharf Bar, 202 William St.

May 30,  in Key West
Sunset Green: Live at Sunset Concert
The Keys Collection presents the "Live at Sunset" free monthly concert series on the last Tuesday of every month on the Sunset Green. The lawn opens at 6 p.m., with local talent performing from 7-10 p.m. Free entry and parking, food & drinks for purchase. Located at 3820 N. Roosevelt Blvd. between The Gates and 24 North hotels.

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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