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Key West Events
Key West events happen all year round. It’s hard to plan a visit to Key West and not have some event happening. I have tried to compile a list of events by the month as I know them so you can plan a visit to Key West around them.
Some events come and go but the big ones have become tradition.
Check out our Key West events calendar. A month by month schedule of events calendar guide to the happenings of our island city. I keep it up and current with what I know is happening for the year here in Key West.
If there is a play, a festival, a concert, or anything else happening in Key West you can find out here! – Just Click the button below.
Key West Events In January 2026
January 1-4, 2026
Pole Vault in Paradise – Experience an exciting pole vault competition set against stunning Key West island views. Perfect for athletes, families, and spectators. https://runsignup.com/Race/FL/KeyWest/PoleVaultInParadise
January 2-12, 2026
Key West Literary Seminar – A world-renowned annual event celebrating the art of storytelling. Founded in 1983, the seminar features a four-day program of readings, lectures, and panel discussions led by some of today’s most acclaimed voices in literature. Participants enjoy a range of community events, book signings, and cultural programs that weave together the island’s historic charm with its vibrant literary legacy. Visitors can also take part in the Key West Literary Walking Tour, exploring the homes and haunts of iconic authors like Ernest Hemingway, Tennessee Williams, and Elizabeth Bishop. For more information: https://www.kwls.org
January 3, 2026
Run for Paradise – 8:00 AM - 10:00 AM, this is a rolling street closure. Race begins at Higgs Beach, to South Roosevelt, turns around and ends at White Street Pier. https://runsignup.com/Race/FL/KeyWest/RunForParadise5k
January 10, 2026
Wounded Warrior Project Soldier Ride – 50+ riders and support staff ride into town from Boca Chica stopping at Bayview Park for a Welcome Ceremony and lunch. Immediately after there is a community ride around historic military sites in Key West. Expect minor delays throughout the route.
January 11, 2026
Wienerpalooza/Chihuahua Flash Mob – This is a rolling street closure. The parade begins at the Custom House at noon and ends at Hank’s Hair of the Dog Saloon. https://doggieparade.com
January 16-18, 2026
Key West Half Marathon and Runfest – https://www.keywesthalfmarathon.com/event-details/
January 16-24, 2026
Southernmost Regatta – Experience the thrill of The Southernmost Regatta in the stunning Florida Keys! Enjoy world-class sailing, vibrant parties, and breathtaking ocean views. Whether you’re a seasoned sailor or a leisure traveler, this unforgettable event blends excitement, relaxation, and island charm. https://www.thesouthernmostregatta.com
January 20-26, 2026
Kelly McGillis Classic – Join the 2026 Kelly McGillis Classic in the beautiful Florida Keys! Enjoy exciting women’s and girls’ flag football tournaments, beachside fun, and vibrant local culture. Perfect for leisure travelers seeking sun, sports, and unforgettable memories. Don’t miss this unique event! https://iwffa.com/kmc-2026/
January 28-31, 2026
King Master – Experience the thrill of the ultimate King Master fishing event in the stunning Florida Keys, where turquoise waters meet endless adventure. Set against this idyllic backdrop, anglers of all levels will compete in a celebration of sport, camaraderie, and natural beauty. The excitement kicks off at the iconic Sloppy Joe’s in Key West, a legendary hotspot known for its lively atmosphere and rich history. https://classicfishingevents.com/king-master-home/
January 27-31, 2026
Mile 0 Fest – Enjoy five days of top Texas Red Dirt & Americana music, beachfront parties, and unforgettable sunsets in Key West. Join fellow music lovers for an epic festival getaway filled with live performances, island vibes, and endless fun. In addition to the music, attendees can enjoy a variety of fun activities, such as Live Music Sails, Pool Parties & more! Mile 0 Fest utilizes the Coffee Butler/Truman Waterfront Park Amphitheater, a beautifully designed facility on the Gulf side of the island. This boutique venue offers an unparalleled view from every conceivable spot – whether it is a VIP tent or a blanket spread out on the grassy hill, every ticket level is sure to thrill. The Amphitheater hosts all evening shows during the festival. Daytime VIP Parties and other events are scattered around the island at hotels, piers, bars, boats, & beaches. https://www.mile0fest.com
Key West Events In February 2026
February 12-16, 2026
Presidential Family Weekend Forum – https://www.trumanlittlewhitehouse.org/foundation/events
February 14-15, 2026
20th Annual Florida Keys Seafood Festival –The 20th Annual Florida Keys Seafood Festival is Saturday, February 14th from 11:00 a.m. to 8:00 p.m. AND Sunday, February 15th from 11:00 a.m. to 5:00 p.m., at Truman Waterfront Park, Key West. There is a $10 admission charge per person for adults, good for both days, which enters that person into a raffle for $250 worth of seafood. Children under 12 are admitted free. https://floridakeysseafoodfestival.com
February 15, 2026
11th Annual Crooks Second Line Parade – https://www.crookssecondlinekw.com
February 21-22, 2026
Key West Art and Craft Festival – Key West’s largest outside art show will be on the Quay in Truman Waterfront Park. https://keywestartcenter.com
Key West Events In March 2026
March 6-8, 2026
Key West Orchid Festival – Annual event put on by the Key West Garden Club. https://keywestorchidsociety.org/annual-orchid-festival
March 7, 2026
Conch Shell Blowing Contest – https://oirf.org/our-events/#
March 9-12, 2026
March Merkin – Invitational Permit Fishing Tournament. For more information visit: https://marchmerkin.com
March 14, 2026
Irish Kevin’s 5K/10K Shamrock Shuffle – St. Patrick’s Day fun Key West style! https://runsignup.com/Race/FL/KeyWest/IK5KShamrockShuffle
March 23, 2026
Taste of Key West – This open-air event offers palate-pleasing small plates beers and wines from over forty Key West restaurants. https://tasteofkeywest.org
March 26-28, 2026
Key West Sailfish Tournament – World-class teams will converge on the waters of Key West for a two day shoot out style tournament, battling it out for the top of the leaderboard and prize money bringing teams from all over Florida and beyond. https://kwst.profishingtournaments.com
Key West Events In April 2026
April 2-4, 2026
Spanish Fly Shark Tournament – Thanks to our partnership with Outdoor America, the tournament is now televised—bringing the excitement of the Florida Keys to a national audience, just like the Madfin series once did. https://keywestsharktournament.com
April 17-26, 2026
Conch Republic Independence Celebration – Join us for lively parades, local music, delicious seafood, and unforgettable island fun. https://conchrepublic.com
Saturday, April 25, 202
Mote Marine Lab’s Ocean Fest – Free, family friendly event with live music, food trucks, kid’s zone and artisan & non-profit vendors at Truman Waterfront Park. https://mote.org/support/signature-events/ocean-fest/
April 29 – May 3, 2026
Key West Songwriters Festival – The largest gathering of its kind in the world, drawing music fans and creators to Key West for five immersive days of live performances, storytelling, and behind-the-scenes insight. Over its multi-day run, the festival features more than 150 to 200 songwriters — from legendary veterans to rising stars — sharing their stories, playing acoustic sets “in the round,” and collaborating in unexpected pairings. Many shows are free to the public, while premium ticketed events provide exclusive access, VIP perks, and deeper connection with the artists. As the island becomes a stage, attendees also enjoy curated events like open-air concerts on Duval Street, sunset performances aboard boats, pop-up sessions at historic venues, and special showcases at landmark hotspots like Sloppy Joe’s. The seamless mix of adjacent genres — country, Americana, folk, and more — amplifies its appeal to diverse audiences. https://www.keywestsongwritersfestival.com
Key West Events In May 2026
May 7-10, 2026
Key West Paddle Classic – https://www.floridakeyswatermancompany.com/keywestpaddleclassic
Key West Events In June 2026
June 3-7, 2026
Key West Pride – This weeklong event welcomes LGBTQ+ visitors, allies, and locals alike, offering a packed schedule of pool parties, drag shows, comedy nights, street fairs, and sunset sail cruises—along with educational programs and cultural tributes that honor the history and resilience of the LGBTQ+ movement. The festival culminates in the spectacular Pride Parade, where revelers dance along Duval Street carrying a 100-foot segment of Key West’s signature Sea-to-Sea flag in a dazzling display of unity and pride. https://gaykeywestfl.com/pride/
June 8-21, 2026
Summer Solstice Celebration – Join us at Mallory Square for the annual Summer Solstice Celebration—a vibrant, nightly festival leading up to the longest day of the year! Enjoy live performances, artisan demonstrations, and interactive experiences each evening starting at 7 PM.
June 12-14, 2026
Swim Around Key West – https://swimaroundkeywest.org
June 13-21, 2026
Annual Dagger Dive – Join us in the stunning Florida Keys for an unforgettable event supporting Task Force Dagger’s mission to assist wounded, ill, or injured U.S. Special Operations members and their families. Enjoy sun, sea, and camaraderie while making a difference for our nation’s heroes.
June 19-21, 2026
VFW Fishing Tournament
Key West Events In July 2026
July 1-5, 2026
Key Lime Festival – this multi-day celebration is held each summer honoring the island’s signature citrus and quirky spirit. Locals and visitors alike dive into a zesty lineup of pie tastings, gastronomic events, contests, live music, and creative activities across multiple venues to celebrate all things Key lime. https://keylimefestival.com
July 19-26, 2026
Hemingway Days & Hemingway Look-a-like Contest – This five-day festival celebrates the legacy of Ernest “Papa” Hemingway. The event blends literary homage with playful contests, waterfront competition, and lively street festivities that draw fans, writers, anglers, historians, and curious travelers alike. Running of the Bulls, the Key West Marlin Tournament, the Hemingway 5K, a Caribbean street fair, and a diverse literary program includes short-story contests, readings, and book events are all part of this festival. https://hemingwaydays.com
Key West Events In August 2026
August 5-9, 2026
Key West Lobsterfest – https://keywestlobsterfest.com
August 12-16, 2026
Tropical Heat – https://gaykeywestfl.com/tropical-heat/
Key West Events In September 2026
September 2-6, 2026
Key West Womanfest – https://gaykeywestfl.com/womenfest/
September 3-7, 2026
Just a Few Friends Key West – Celebrate the island spirit at the four-day tribute to Jimmy Buffett’s legacy in Key West, where it all began. This lively event features live music, island-inspired food and drinks, and a full lineup of festivities honoring the tropical lifestyle Buffett loved and shared. From unforgettable performances to laid-back gatherings with fellow Parrot Heads, it’s a weekend of good vibes, great tunes, and Margaritaville magic. Don’t miss this heartfelt celebration of music, community, and the island way of life. https://www.justafewfriendskeywest.com
September 5-6, 2026
CFK Pentathlon Swim Meet & Key West Open Water Swim – The Open Water Swims take place following the start of The College of the Florida Keys Swim Around Key West at Higgs Beach. Participants will swim a scenic loop course in the clear, warm Atlantic waters, surrounded by marine life like fish, coral, turtles—and maybe even dolphins or mermaids! No personal support crew is needed, as lifeguards in kayaks and boats ensure swimmer safety. The award ceremony for the 800-yard, 1-mile, and 2-mile events will be held immediately after the 2-mile swim concludes. https://swimaroundkeywest.org/event-details-open-water/
Key West Events In October 2026
October 16-25, 2026
Fantasy Fest
Quite possibly the mother of all Key West events. A week or so long festival of anything a person can imagine and more. Fantasy fest has a theme for every day of the festival and parties and get togethers. Things like Toga Night and Tu Tu Tuesday.
Pre leading Fantasy Fest there is Goombay Festival full of food and music getting us all ready for Fantasy Fest.
Key West Events In November 2026
November 1-8, 2026
Key West World Championship Power Boat Races – https://raceworldoffshore.com/key-west/
Key West Events In December 2026
Christmas Lights In The Tropics – December 18th end of the month. Who doesn’t like Christmas lights? Roll the dice on climate for feeling like Christmas we can sure there will be not be snow. There are tours self guided and guided to see the houses in Key West that participate in their own way to celebrate Christmas in Key West.
Key West Christmas Parade – Come see the southernmost Christmas spectacular. Parade route goes through Key West and right down Duval Street. A great time for all ages and lots of candy being tossed from parade floats. Santa Will be making an appearance. (probably wearing something tropical).
December 31, 2026
New Year’s Eve Celebrations!
Click Here For The Best – Key West Sandbar Trips
Check out which cruise ship will be in Key West and when by looking at my Key West cruise ship schedule. As soon as the cruise lines release the dates I will have them here. Key West has been a cruise port since the early 90s. They bring a number of tourists here nearly every day. Ships from all the major cruises come to Key West.