Eclectic Events Highlight Florida Keys’ 2025 Calendar

FLORIDA KEYS — There’s always something happening in the Florida Keys & Key West, from eclectic festivals focusing on the area’s colorful history, arts and notable cuisine to events that celebrate the Keys’ unique environment, underwater adventures and quirky ambiance. 

While this listing contains selected highlights for 2025, the Florida Keys & Key West also feature a vibrant cultural community that presents theatrical productions, musical performances, film screenings, lecture series and more. 

Of course, event dates may change due to unforeseen circumstances. A comprehensive and frequently updated year-round calendar of Keys events can be found at fla-keys.com/calendar. 

March 2025

The second annual St. Paddy’s Island Run 5k/10k (March 16; runsignup.com/Race/FL/Islamorada/StPattysIslandRun) is hosted by Florida Keys Brewing Company in Islamorada. Runners are to receive a free beer, finisher’s medal and T-shirt — and can enjoy a St. Paddy’s party in the beer garden after the race. 

NAS Key West Southernmost Air Spectacular (March 29-30; keywestairshow.com) brings high-flying action to Naval Air Station Key West’s Boca Chica Field near Key West, with aerial demonstrations by military and civilian performers including the U.S. Navy Blue Angels flight demonstration team. 

April 2025

The 7 Mile Bridge Run (April 5; 7mbrun.com) attracts a field of 1,500 runners to the city of Marathon each year to compete on a course across one of the world’s longest segmental bridges, the centerpiece of the Florida Keys Overseas Highway.

The Florida Keys Island Fest (April 5-6; islamoradachamber.com/island-fest) highlights nearly 100 artists and crafters in a juried art show, along with live music, homemade boat races and a “Taste of Islamorada” competition for foodies. The 33rd annual event takes place at Islamorada’s Founders Park.

The Historic Days Celebration (April 3-6); keywesthistoricdayscelebration.com) highlights the Key West Woman’s Club’s 110th anniversary with history-focused tours, presentations, and panel discussions at the club’s headquarters, the Hellings Curry Museum, and other island locations. Receptions are planned featuring appetizers prepared from recipes in the “Key West Woman’s Club Cookbook,” while other events include a High Tea of Years Gone By. 

The 43rd annual Conch Republic Independence Celebration (April 18-27; conchrepublic.com) commemorates the Florida Keys’ symbolic 1982 secession from the United States and rebirth as the independent and eccentric Conch Republic. Events are held in Key West and typically include a parade along Duval Street, a mock battle at sea with tall ships, sunset sailing cruises, parties and the wacky Great Conch Republic Drag Race.

May 2025

The Key West Songwriters Festival (April 30-May 4; facebook.com/keywestsongwritersfest) features America’s foremost performing songwriters and artists at dozens of concerts staged in intimate, audience-friendly Key West settings. Typically included are more than 50 shows and 200-plus country and pop hitmakers. Now in its 29th year, the festival revolves around five days and nights where live music bliss introduces crowds to the faces, voices and stories behind the songs. 

The I.CARE Trash Derby and Festival (May 1-4; icaretrashderby.com) includes two days of trash collection by scuba divers and on-land participants, who compete for prizes for the largest hauls at cleanup locations throughout the Keys. Divers can register with their favorite dive shop while non-divers can assemble teams for land-based debris removal. A public festival May 4 at Islamorada’s Founders Park celebrates the cleanup with award ceremonies, live music, food and booths by Florida Keys conservation organizations. 

June 2025

The College of the Florida Keys Swim Around Key West (June 14); swimaroundkeywest.org) is a 12.5-mile endurance swim, open to individuals and relay teams, around the island of Key West through Atlantic Ocean and Gulf of Mexico waters. Organized by The College of the Florida Keys, it’s billed as the only sanctioned, insured and U.S. Coast Guard-permitted swimming race around Key West. Associated events include shorter open-water swims. 

Key West Pride (June 22-29; gaykeywestfl.com/pride/) features a lively roster of fun for Key West’s LGBTQ visitors, friends and allies on the island known for its accepting “One Human Family” atmosphere. Events typically include pool parties, late-night drag shows and soirees, on-the-water adventures, a street fair, pageants and a colorful parade.

July 2025

The Key Lime Festival (July 3-7; keylimefestival.com) in Key West celebrates the world’s most sensational citrus with a bountiful array of festivities across the island where Key lime pie was conceived. Over five days, lovers of the lime can indulge in activities including a gravity-defying Key lime pie drop competition from the top of the Key West Lighthouse, a Key lime cocktail sip and stroll, Key lime brunches and dinners, and the world-famous Key lime pie eating championship set for July 4.

Celebrating Freedom Parade & Fireworks (July 4; 305-451-1414) in Key Largo is the Upper Keys area’s 49th annual salute to America’s independence. The fun kicks off with a midmorning community parade featuring patriotic floats along the Florida Keys Overseas Highway. The Celebrating Freedom event with live music and vendors takes place in the evening, culminating in a magnificent fireworks show over Blackwater Sound.

The 41st annual Underwater Music Festival (July 11-12; lowerkeyschamber.com), a sub-sea concert staged to promote environmentally responsible diving and reef protection, begins with a July 11 welcome event at Mote Marine Laboratory’s Summerland Key facility. On July 12, divers and snorkelers submerge at Looe Key Reef alongside costumed characters “playing” faux instruments. Participants listen to ocean-themed music that’s piped underwater, interspersed with messages about ways to enjoy the underwater world while minimizing environmental impacts. 

Hemingway Days (July 22-27; hemingwaydays.com); honors the literary legacy and Key West lifestyle of Ernest Hemingway, the American literary giant who lived and wrote on the island for most of the 1930s. Events include the legendary Hemingway Look-Alike Contest at Sloppy Joe’s Bar, the wacky Running of the Bulls, a commemoration of the 126th anniversary of Hemingway's birth, a museum exhibit, a marlin tournament, a 5k run and a street fair.

August 2025

At Key West Lobsterfest (Aug. 7-10; keywestlobsterfest.com), seafood lovers can chow down on Florida’s clawless lobster. The tasty “feast-ival” features a savory schedule of events ranging from a traditional lobster boil to a pub crawl, pool parties, a brunch, and the lively annual street fair and concert Aug. 9. 

The City Bikes Key Largo Triathlon (Aug. 15-17; gameonraceevents.com) set at Key Largo’s John Pennekamp Coral Reef State Park, brings athletes of all ages to compete in Olympic and sprint distance triathlon and duathlon races as well as an Olympic distance aquabike race.

Just a Few Friends Key West (Aug. 29-Sept. 1; justafewfriendskeywest.com) is a memorial celebration honoring Key West’s favorite son, Jimmy Buffett, on the second anniversary of his Sept. 1, 2023 passing. The weekend is filled with tours, bar crawls, rum tastings and music events. The highlight is the Second Line Parade along Duval Street, culminating in a free music festival at Truman Waterfront Park with local and national entertainment. 

September 2025

Womenfest Key West (Sept. 3-7; gaykeywestfl.com/womenfest) is Key West’s popular annual festival for lesbians and their friends — designed to enable singles, couples and groups of women to experience the atmosphere of openness and acceptance that has made Key West an internationally acclaimed lesbian and gay vacation destination. Activities range from beach parties, snorkeling and sunset cruises to live entertainment and more.

The Swim for Alligator Lighthouse (Sept. 13; swimalligatorlight.com) is a world-class, 8-mile open-water swim to the iconic Alligator Reef Lighthouse and back to shore in Islamorada. The unique and challenging experience can be conquered solo or on 2-, 3- or 4-person relay teams. Proceeds from the race go toward the effort to fully restore the 152-year old lighthouse.

October 2025

Taste the Keys (Oct. 1-31; tastethekeys.com) provides a culinary journey through Key Largo and the Upper Keys to experience delectable Florida Keys cuisine on weekly foodie tours by trolley, culminating in a cook-off competition event. Participating locations include Skipper’s Dockside, Playa Largo, The Catch, Gus’ Grille at Reefhouse Resort & Marina, Mrs. Mac’s and many more. 

REEF Fest (Oct. 16-19; reef.org/reeffest), hosted by the Reef Environmental Education Foundation in Key Largo, enables ocean lovers to celebrate their love of marine life and learn about the latest in conservation through dive, snorkel and kayak trips along with ocean-themed seminars and social events. 

Key West Fantasy Fest (Oct. 17-26; fantasyfest.com) is an annual 10-day costuming and masking extravaganza that features dozens of exciting and exotic events. The theme for 2025 is “Bedtime Stories & Magical Monsters.” The fun begins with the exuberant Goombay Festival and continues with standouts including the Royal Coronation of the 2025 Fantasy Fest king and queen, lavish Headdress Ball, wacky and wonderful Key West Pet Masquerade, colorful Captain Morgan Masquerade March, and the world-famous Key West Fantasy Fest Parade set for Oct. 25. 

The Zombie Bike Ride (Oct. 19; zombiebikeride.com) features thousands of “the bicycling dead” in a lighthearted pre-Halloween trek along Key West’s Atlantic Ocean shoreline and streets. Visiting and local adults, kids and even a few pets dress in offbeat zombie garb, ragged finery and scary face paint for the spooky spectacle, which also includes “Zombieland” pre-ride festivities and a rollicking after party. 

November 2025

The Race World Offshore Key West World Championship (Nov. 2-9); raceworldoffshore.com/key-west) brings the world’s top powerboat teams to compete in high-speed races in the waters surrounding the island city. Activities include a parade of powerboats and teams down Duval Street, parties, concerts, and viewing from the Race Village at Truman Waterfront Park and from waterfront hotels and restaurants. The spectator-friendly course layout means fans can watch from vantage points breathtakingly close to the action.

The Key West Film Festival (November dates to be announced; keywestff.com), named one of the top 25 coolest film fests in the world by Moviemaker magazine, includes screenings of as many as 75 films, panel discussions, parties and the presentation of awards including the Golden Key for emerging talent and excellence in costume design. 

Key West Holiday Fest (Nov 26-Dec. 31; keywestholidayfest.com)  includes a merry range of celebrations during Key West’s busy holiday season, starting the night before Thanksgiving and ending on New Year’s Eve. Events traditionally include the lighting of the Harbor Walk of Lights, tours of historic inns, a lighted boat parade, festive Old Town Trolley and Conch Train tours to see neighborhoods elaborately decorated with holiday lights, seasonal artisan markets and bazaars, and quirky New Year’s Eve “drops” that spoof New York City’s annual Times Square “ball drop.” 

December 2025

Experience a Waterfront Winter Wonderland (Dec. 12-27; waterfrontwinterwonderland.com) at Key West’s Coffee Butler Amphitheater in Truman Waterfront Park. Despite the island’s typically balmy holiday breezes, the festive grounds “chill” with an ice skating rink and “snow” showers. The family-friendly event features rides including a Ferris wheel, a carousel, swings and giant slides. Visits with Santa and live music add to the holiday atmosphere. 

New Year’s Eve (Dec. 31) in Key West includes a series of delightfully quirky “drops” that spoof New York City’s annual Times Square “ball drop.” Standout celebrations to welcome the New Year include the midnight “drop” of a female impersonator in a spangled super-sized red high heel shoe outside the Bourbon St. Pub/New Orleans House complex; the “drop” of a gigantic manmade conch shell atop the roof of Sloppy Joe’s bar; the lowering of a “pirate wench” from atop the mast of the tall ship America 2.0 at Schooner Wharf Bar; and the midnight “landing” of a replica Pan Am aircraft carrying a costumed flight attendant at First Flight Island Restaurant & Brewery.

Florida Keys calendar of events: fla-keys.com/calendar