2025 Events & Festivals
Jan 10, 2025
Key West Art & Historical Society Historic Seaport Sail: Harry S. Truman in Key West
Enjoy a 2-hour Historic Harbor Tour with Truman Little White House docent Rick Warmbold on the S/V Argo Navis, talking about “Harry S. Truman’s Eleven Key West Visits.” The trips departs from the Historic Seaport docks at 0 Margaret St. at 10 a.m. and returns at 12 p.m. Passengers will enjoy Bloody Marys, mimosas, or non-alcoholic beverages along with lite breakfast fare as Warmbold dives into Truman’s eleven working vacations, and shares how Key West was not only a place for the President to recharge his batteries – he will tell you how things in Key West would shape the country and world. Book reservations online in advance.
Jan 10, 2025
Key West Outdoor Movies
Key West Outdoor Movies presents a family-friendly film (to be named) at the parade grounds at Fort East Martello, 3501 S. Roosevelt Blvd. The grounds open at 5 p.m. with free admission. Food and drink will be available for sale by vendors onsite, and there will be free popcorn and activities for all. Bring low chairs or a blanket. The movie starts at dusk.
Jan 15, 2025 – Jan 19, 2025
Key West Kingfish Mayhem
Angling teams targeting kingfish can vie for mastery and substantial cash prizes during the 2025 Key West Kingfish Mayhem tournament. The open division team that weighs in the heaviest kingfish, also known as king mackerel, is to take home a $75,000 first prize with $35,000 and $20,000 going to the second and third place teams, respectively. The tournament is headquartered at The Perry Hotel & Marina.
Jan 18, 2025 – Jan 19, 2025
Key West Half Marathon & Runfest
The 27th Anniversary of the Key West Half Marathon & 5k will take place during the week-end of January 18-19, 2025. On top of previous years race day events, this years race will include the Papa’s Pilar Rum Stroll and Key West Beach N’ Beer Mile!
Jan 20, 2025 – Jan 25, 2025
The Southernmost Regatta
Top sailing teams from around the world 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, mingle with sailors and view sailboats at the Galleon Resort’s marina, 617 Front Street, after each day’s races.
Jan 21, 2025 – Jan 27, 2025
Kelly McGillis Classic International Flag Football Championship
Women from countries far and wide will be descending upon Key West for the 32nd annual flag football competition with teams participating from USA, Morocco, Spain, Mexico, Sweden, Pakistan, Mexico, Honduras and El Salvador. Kelly McGillis will serve as grand Marshall for the players’ parade from the historic seaport down Duval Street on Thursday, Jan. 25. Game activities throughout the weekend Jan. 26-28 are free for the public to attend at Wicker Field Sports Complex on Kennedy Drive off Flagler Ave.
Jan 21, 2025 – Jan 25, 2025
Mile 0 Fest
Mile 0 Festival is a premier music festival that celebrates Red Dirt and Americana music. Artists includes the Red Clay Strays, Randy Rogers Band, Shane Smith & the Saints, Steve Earle, Reckless Kelly, Kaitlin Butts and many more. A variety of passes that include lodging are available along with event-only passes.
Jan 22, 2025 Key West
Key West Theater: Melissa Etheridge
Don’t miss the legendary Melissa Etheridge on the Key West stop of her 2025 tour. Known for her confessional lyrics and raspy, smoky vocals, Etheridge has remained one of America’s favorite female singer-songwriters for more than two decades. Doors at 7 p.m.; show at 8 p.m. 512 Eaton Street.
Jan 25, 2025 – Jan 26, 2025
Big Pine & Lower Keys Nautical Expo
The LKCC welcome you Saturday Jan 25 8am-4pm and Sunday Jan 26 8am-2pm to one of our biggest events with over 100 vendors. This event is fun for the whole family and includes an array of nautical pieces and much more that makes Florida Keys living great
Feb 9, 2025
Conch Republic Polar Plunge
All brave souls are welcome for the 15th Annual Southernmost Conch Republic Polar Plunge, a cherished tradition benefiting the programs of Samuel’s House supporting the homeless in Key West. Take the plunge into the cool Atlantic Ocean waters at Higg’s Beach in front of Salute Restaurant, 1100 Atlantic Boulevard at 12 p.m. (noon) on Super Bowl Sunday. Your $50 registration includes an event T-shirt, a cool symbol of your support.
Feb 15, 2025 – Feb 16, 2025
Florida Keys Seafood Festival
The 19th annual Florida Keys Seafood Festival takes place Saturday from 11 a.m. to 8 p.m. and Sunday from 11 a.m. to 5 p.m. at Truman Waterfront Park, located at the end of Southard Street. Everything Florida Keys seafood is on the menu, including fish baskets and platters, grilled spiny lobster, peel and eat Key West pink shrimp, smoked fish dip, Bahamian conch chowder and more. Attendees can enjoy adult beverages, live music, great shopping and art and a children’s eco discovery zone.
Feb 17, 2025
Coffee Butler Amphitheater: Willie Nelson & Family
With a seven-decade career, Willie Nelson has earned every conceivable award as a musician and amassed reputable credentials as an author, actor, and activist. He continues to thrive as a relevant and progressive musical and cultural force. The iconic entertainer returns for a show Feb. 17 at 7 p.m. with family members and featured artist Randall King at Coffee Butler Amphitheater, 21. E. Quay Rd.
Mar 8, 2025
Conch Shell Blowing Contest
An island tradition, this unique contest celebrates the historic importance of conch in the Keys and features contestants in several age categories attempting to make “music” with fluted conch shells. The contest takes place in the garden of the Oldest House, 322 Duval Street. It’s free to participate in, and to attend. All ages are invited to compete. Registration begins at 10 a.m., the contest starts at noon.
Mar 10, 2025 – Mar 13, 2025
March Merkin Invitational Permit Tournament
This charity flats-and-fly-only invitational tournament, presented by the Lower Keys Guides Association, challenges anglers to catch and release silvery permit to vie for elite titles. The event is held at Oceans Edge Key West Resort & Marina, 5950 Peninsular Ave.
Mar 14, 2025 – Mar 16, 2025
Robert the Doll Paranormal Weekend
Experience a weekend in Key West full of supernatural events including exclusive haunted tours, seances and other paranormal experiences with ghost hunters and paranormal experts.
Mar 22, 2025 – Mar 23, 2025
Latin Festival Key West
Enjoy a lively combination of food, music and culture during the family-friendly Latin Festival at Bayview Park, 1320 Truman Ave. Restaurants participating include El Siboney, El Mocho, El Habanero, Sandy’s Cafe and more.
Mar 29, 2025 – Mar 30, 2025 Key West
NAS Key West Southernmost Air Spectacular
The Blue Angels & other military & civilian acts will fill the skies of the Florida Keys March 29-30th, at the NAS Key West Southernmost Air Spectacular air show at Boca Chica Field.
Apr 3, 2025 – Apr 5, 2025
Spanish Fly Shark Tournament
The 2nd annual Spanish Fly Shark Tournament comes to Key West Yacht Club, 2315 N. Roosevelt Blvd. with another exciting event dedicated to gathering data on the bull shark population in the Keys. The tournament action is to be filmed for broadcast by Outdoor America. All captains or boat owners must have an HMS permit with a shark endorsement.
Apr 12, 2025
Truman Waterfront Park: Mote Marine’s Ocean Fest
Underwater and outdoor enthusiasts, ecotravelers and families are encouraged to celebrate the marine environment at Mote’s Ocean Fest: A Community Celebration. Proceeds and donations from the festival support Mote Marine Laboratory’s coral reef restoration and research programs. From 10 a.m.–3 p.m. in Truman Waterfront Park, 0 Southard St., enjoy a fun day of crafts, games, music, food, local brews (for ages 21+) and shopping, and explore conservation and environmental exhibits. Meet Mote scientists along with other conservation and environmental organizations from around Florida, and learn about the work they are doing and how you can help.
Apr 19, 2025
Earth Day 5k Run/Walk
The Key West Southernmost Runners’ 26th annual Earth Day 5k Run/Walk takes place Saturday at Truman Waterfront Park at the end of Southard St. The start and finish line is near the U.S .Coast Guard Cutter Ingham Maritime Museum. Proceeds from the race benefit the Conch Republic Marine Army, a local non-profit grassroots organization dedicated to cleaning and restoring the shallow mangrove habitats of the Florida Keys.
Apr 26, 2025
Tropic Cinema: Movies Under the Stars – Spaceballs
Don’t miss the monthly free Movies Under the Stars screening – this month, the movie is Spaceballs. The film will be presented free for all, outdoors on Eaton Street. Bring chairs or blankets for seating. Concessions are to be available in the theater lobby. The film begins a half hour after sunset. 416 Eaton St.
Apr 30, 2025 – May 4, 2025
29th Annual Key West Songwriters Festival
The Key West Songwriters Festival is the largest festival of its kind in the world. It revolves around five days and nights where live music bliss introduces crowds to the faces, voices and stories behind the songs. Performances take place at numerous theaters, bars and event spaces around Key West.
Jun 13, 2025 – Jun 15, 2025
Key West Gator Club Dolphin Derby
Anglers targeting dolphin fish can compete for $15 thousand in guaranteed cash prizes during the Key West Gator Club Dolphin Derby June 13 through 15. Tournament location to be announced. The team weighing in the heaviest dolphin fish takes home a grand prize of $5 thousand. Proceeds benefit scholarships for Key West High School graduates attending University of Florida.
Jun 22, 2025 – Sep 1, 2024
Key West Pride
Celebrate PRIDE on the tropical island of Key West that is legendary for its laid-back style and its open and accepting atmosphere. Whether you’re looking to party with friends, travel with family, or to get lost in the magic of the southernmost city, rediscover Key West and discover how the island has created one of the most integrated and unique communities in the world. Show us your pride, we will show you our Key West Pride!
Jul 22, 2025 – Jul 27, 2025
Hemingway Days
Ernest Hemingway look-alikes, writers, anglers, and fans of the late author’s work are to gather in Key West for the annual Hemingway Days celebration. The festival honors the legacy of the American literary giant who lived and wrote on the island for most of the 1930s. Events include the legendary Hemingway Look-Alike Contest, the wacky Running of the Bulls on Sat. July 26, literary presentations, a commemoration of the 126th anniversary of Hemingway’s July 21 birth, a museum exhibit, a marlin tournament, a 5k run and paddleboard race, a street fair and more.
Aug 29, 2025 – Sep 1, 2025
Just a Few Friends Key West
Join us in Key West for Labor Day weekend to celebrate the 2nd Annual Just a Few Friends memorial, honoring our favorite son, the late Jimmy Buffett. Festivities kick off with an official pre-party meetup on Thursday, August 28. On Friday morning the City of Key West will proclaim “State of Florida Jimmy Buffett Day,” followed by activities on and off the water, foodie events, and great times. Saturday features a run/walk, the Margarita Bar Crawl, along with tours, lectures, rum tastings, and music events across town. Sunday’s highlight is the epic Second Line Parade starting at 5 pm culminating in a free music festival at Truman Waterfront Park with local and national entertainment, food trucks and vendors. Come Monday continue the celebration with a variety of activities and entertainment options to suit every interest.
Oct 17, 2025 – Oct 26, 2025
Key West Fantasy Fest
“Bedtime Stories & Magical Monsters” is the official theme for Fantasy Fest 2025, Key West’s annual multi-day costuming extravaganza in paradise. From October 17-26, revelers can explore an array of exciting events, including the the exuberant Goombay Festival in the streets, the Zombie Bike Ride, a Bedtime Stories and Magical Monsters-themed 5K run/walk, the Captain Morgan Masquerade March (aka “Locals Parade”), the Royal Coronation of the 2025 Fantasy Fest King and Queen, plus concerts, theater productions, the enchanting Key West Pet Masquerade, the 41st annual Headdress Ball pageant, and the world-famous Key West Fantasy Fest Parade on Saturday, Oct. 25.
Dec 31, 2025
Rigging in the New Year at Schooner Wharf
The popular waterfront watering hole once again will present its unique and original nautical New Year’s Eve tradition with “The Lowering of the Pirate Wench” from the towering mast of the tall ship America 2.0 docked in front of the bar in the Key West Bight.