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. 

January 2025

The Key West Literary Seminar (Jan. 9-12; kwls.org) presents some 20 leading American and international writers, exploring the topic of “Family” in solo and paired readings, lectures, and panel discussions. The keynote speaker is John Irving, renowned author of “The World According to Garp” among other standouts. Headquartered at Key West’s San Carlos Institute, the seminar includes Sunday afternoon presentations that are open to the public.

The Florida Keys Celtic Festival (Jan. 11-12; floridakeyscelticfestival.com) enables visitors to experience the sights and sounds of the Scottish Highlands and the Emerald Isle in Marathon in the Middle Florida Keys. Attractions include live music by Albannach, The Screaming Orphans, Jamison and West of Galway, plus bagpipers, Irish dancers, highland athletic games, sheep herding demonstrations, authentic Celtic food, children's games, vendors and more. 

The Southernmost Regatta (Jan. 20-25; southernmostregatta.com) brings top sailing teams from around the world to compete in the azure waters off Key West, showcasing colorful sails and avid sportsmanship during five consecutive days of racing. Competition is open to One Design and ORC Racing/Cruising Keelboats. Spectators can watch the races from various waterfront venues.

The Key West Half Marathon & Runfest (Jan. 18-19; keywesthalfmarathon.com) attracts thousands of runners from around the U.S. and other countries to compete in a top U.S. winter half marathon, run beside the Atlantic Ocean, and enjoy Key West’s typically balmy “winter” weather. The half marathon takes place Jan. 19, with shorter races and additional events rounding out the schedule. 

Mile 0 Fest (Jan. 21-25, mile0fest.com) features more than 60 celebrated musicians and bands from the Americana and “Red Dirt” genres, all performing in subtropical Key West. Attendees can enjoy five nights of open-air main stage shows at the Coffee Butler Amphitheater, plus acoustic jams and songwriter swaps at other island locations. 

The 33rd annual Kelly McGillis Classic International Women’s & Girl’s Flag Football Championship (Jan. 21-27; iwffa.com) in Key West is expected to draw more than 30 teams of women and girls representing the U.S. and countries around the world for flag football games along with team-building activities and social gatherings. The popular event is named for McGillis, the “Top Gun” movie actress and former Key West resident.

The Island Boat Show (Jan. 24-26; islandboatshow.com), billed as the Florida Keys’ premier boat show, is held on the grounds of Island Community Church in Islamorada. Planned attractions include top boat brands and dealers, a large silent auction, food and drink vendors, and nautical merchandise for the entire family.

The Big Pine & Lower Keys Nautical Expo (Jan. 25-26; lowerkeyschamber.com) brings more than 100 vendors to Big Pine Key for a large marine marketplace event. Attendees can find values on gear and everything imaginable for boating, fishing, diving and more, plus marine-influenced clothing, art, jewelry and crafts, live entertainment, food and beverages. The event takes place on the grounds of the Lower Keys Chamber of Commerce visitor center. 

February 2025

The Winter Star Party (Jan. 27-Feb. 2; scas.org/winter-star-party) draws several hundred astronomers and astro-imagers from around the world to view southern constellations, comets and stars in the Lower Florida Keys’ clear night skies — virtually the only place in the continental U.S. where they can be viewed. Lectures, programs and other attractions round out the event that’s held beside the Atlantic Ocean at Scout Key. 

The Upper Keys Garden Walk (Feb. 15; gardenclubupperkeys.org) is a unique self-guided tour that showcases beautiful private garden properties in the Upper Keys. The event also includes an art show and Garden Market. 

The Florida Keys Seafood Festival (Feb. 15-16; floridakeysseafoodfestival.com) at Key West’s Truman Waterfront Park features the freshest Keys seafood — all caught, cleaned, prepared and served by local fishermen. Other attractions include live music, an eco-discovery zone for kids, and vendors selling Keys-made wares and art. 

Presidential Families Weekend (Feb. 15-17; trumanlittlewhitehouse.org/foundation/events) celebrates Presidents’ Day weekend at the state of Florida’s only presidential site, the Harry S. Truman Little White House. Events include a panel discussion with presidential descendants, performances of the stage production, “Give ‘Em Hell, Harry!” and a President’s Day cookout. 

The Sombrero Beach Run (Feb. 21-23; sombrerobeachrun.org) in Marathon attracts several hundred people for a weekend of running and sunning. The running event is held Saturday, Feb. 22, at Sombrero Beach, located at the end of Sombrero Beach Road at mile marker 50. Awards are given to overall finishers in a 5k walk and 5k and 10k runs. Those completing the event’s 15k challenge receive special gifts. Celebrations and beach activities fill the weekend. 

The Key West Art & Craft Festival (Feb. 22-23; keywestartcenter.com) is a juried show that draws scores of artists and artisans displaying their creations. Vendor booths are set up along the harbor at Key West’s Truman Waterfront Park, and the popular event also features artist demonstrations.

The Gigantic Nautical Market (Feb. 22-23; rotarynauticalmarket.com) in Islamorada brings bargains on everything nautical including boats, dive gear, furnishings for boat and home, art, clothing, fishing gear and more from hundreds of vendors. Plans call for as many as 18 food trucks on the grounds of Islamorada’s Founders Park during the event. 

March 2025

The Conch Shell Blowing Contest (March 8; oirf.org) has been a Key West tradition for over 60 years. Held at the Oldest House Museum and Garden, the unique challenge celebrates the historic importance of the conch mollusk in the Keys and features contestants from toddlers to seniors attempting to make “music” using fluted conch shells.

The Original Marathon Seafood Festival (March 8-9; marathonseafoodfestival.com) lures thousands of seafood lovers to the Middle Keys to savor Keys-harvested seafood including lobster, stone crab, shrimp and fish prepared and served by Florida Keys fishermen. Additional attractions at the family-friendly feast include musical acts, raffles, prizes, a kids’ area and vendors offering artisan wares. 

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