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.
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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 2027
January starts off our year with lots of things to do. A great time to visit Key West with perfect weather for land based Key West events.
January 7-10, 2027
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 7-10, 2027
Pole Vault in Paradise – Experience an exciting pole vault competition set against stunning Key West island views. Perfect Key West event for athletes, families, and spectators. https://runsignup.com/Race/FL/KeyWest/PoleVaultInParadise
January 10, 2027
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 15-17, 2027
Key West Half Marathon and Runfest – https://www.keywesthalfmarathon.com/event-details/
January 18-22, 2027
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 19-25, 2027
Kelly McGillis Classic – Join the 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!
January 26-30, 2027
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
January 27-31, 2027
Key West Food and Wine Festival – The Key West Food & Wine Festival proudly welcomes you to a spectacular global journey across five continents: Europe, South Africa, North America, South America, and Oceania. As the world’s premier wine-producing regions, their landscapes, heritage, and flavors will take center stage right here in paradise. This year’s festival is driven by a simple philosophy: the food, the stories, the culture, and the chefs who bring them to life.
February 2027
February 13, 2027
12th Annual Crooks Second Line Parade – https://www.crookssecondlinekw.com
February 13-14, 2027
Annual Florida Keys Seafood Festival –The Annual Florida Keys Seafood Festival is Saturday, from 11:00 a.m. to 8:00 p.m. AND Sunday, 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 20-21, 2027
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
February 24-28, 2027
LEAD Fest Circus – L.E.A.D. FEST events bring rides, food, shows, and much more to communities across the U.S. From carnivals to fairs, concerts to circuses, we have something for everyone! Join us in our mission to help create safer, healthier communities free of drugs, bullying, and violence across the United States. Learn more about L.E.A.D. on our website: LEADrugs.org.
March 2027
March 5-7, 2027
Key West Orchid Festival – Annual event put on by the Key West Garden Club. https://keywestorchidsociety.org/annual-orchid-festival
March 9-12, 2027
March Merkin – Invitational Permit Fishing Tournament. For more information visit: https://marchmerkin.com
March 10-13, 2027
King Master Key West – 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, King Master’s Host Sponsor in Key West, a legendary hotspot known for its lively atmosphere and rich history. https://www.fishkingmaster.com
March 12-13, 2027
Key West Jeep Invasion – Put on by Seven Slot Sales, LLC DBA Blinkerfluid Productions at the Truman Waterfront Park 103 Field, Parking Lot, Quay Wall, playground side of boat ramp, and the gravel lot on Friday, March 12, 2027 and Saturday, March 13, 2027, from 10:00 A.M. to 4:00 P.M.
March 13, 2027
Irish Kevin’s 5K/10K Shamrock Shuffle – St. Patrick’s Day fun Key West style! https://runsignup.com/Race/FL/KeyWest/IK5KShamrockShuffle
March 20-21, 2027
Florida Keys Latin Festival – This is where the flavors, rhythms, and traditions of Latin America and the Caribbean come alive in the heart of Key West. Hosted in the beautiful Bayview Park, the festival features electrifying performances from local and international Latin artists, delicious food from top Cuban and Latin restaurants, and a lively atmosphere that celebrates community and culture. Don’t miss the chance to experience the vibrant spirit that makes South Florida so special. https://floridakeyslatinfestival.com
TBD
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
April 2027
April 5, 2027
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
April 8-10, 2027
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 8-10, 2027
Key West Rodeo Billfish & Meat Tournament and Dock Fest – The Salty Dawgs Key West Rodeo brings competitive fishing to the heart of Key West. Weekend warriors, charter crews and competitive teams from near and far are all invited to take their shot at the Key West Rodeo. The Rodeo brings together local & travel teams, entertainment, local businesses, marine brands, good food, great drinks, and the Key West Community. Built for great fishing, chances to win BIG, and a damn good time in Key West. https://www.keywestrodeotournament.com
April 14-18, 2027
Viking Challenge – The Viking Key West Challenge brings the Viking and Valhalla community together in Key West for a week of family, fishing and fun. The tournament blends competition on the water with camaraderie, special events and time together in one of boating’s great destinations. https://www.keywestchallenge.com/index.asp
April 16-25, 2027
Conch Republic Independence Celebration – Join us for lively parades, local music, delicious seafood, and unforgettable island fun. https://conchrepublic.com
April 25 – May 2, 2027
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
TBD
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/
Key West Events In May 2027
April 25 – May 2, 2027
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
May 8, 2027
Key West Paddle Classic – https://www.floridakeyswatermancompany.com/keywestpaddleclassic
June 2026
June is the beginning of our summers. A great time to visit for some really fun Key West events. One of the best months for Key West Fishing.
June 2-6, 2027
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 13-21, 2027
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, 2027
Swim Around Key West – https://swimaroundkeywest.org
June 22-26, 2027
Mango Fest – From vendors to drinks, educational experiences, trees and fresh mangoes, we strive to carry on a tradition for the love of mangos that you won’t forget!Enjoy live music and entertainment from local artists while you indulge in your favorite mango filled foods.Bring the whole family for a day of fun and games. We have a dunk tank, water slide, and other fun activities for kids of all ages. https://mangofestkeywest.com
June 30 – July 4, 2027
Key Lime Festival – this multi-day Key West 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
TBD
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.
TBD
Florida Keys PBA Dolphin Tournament – https://www.keysdolphintournament.com
TBD
VFW Fishing Tournament – https://vfw3911.org/di/vfw/v2/default.asp?nid=2
July 2027
June 30 – July 4, 2027
Key Lime Festival – this multi-day Key West 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 21-25, 2027
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
TBD
Key West Lionfish Derby – The Key West Lionfish Derby is about more than trophies and prizes. Lionfish are an invasive species in the Florida Keys, and removing them from our reefs is an important part of protecting our local marine ecosystem. Every lionfish removed represents one less invasive predator on our reefs. https://finzdivecenter.com/lionfishderby/
August 2027
August 11-15, 2027
Key West Lobsterfest – Join us as we dive into the vibrant atmosphere, live music, and “crustacean celebration” that makes Lobsterfest a signature Key West tradition. Whether you’re here for the buttery tails or the island vibes, this is one summer celebration you won’t want to miss! https://keywestlobsterfest.com
August 11-15, 2027
Key West Rumfest – Celebrating Key West’s favorite spirit! https://rumfestkeywest.com
August 11-15, 2027
Tropical Heat – The HOTTEST annual 5-day party for gay men ages 21 and up in Key West and the Florida Keys! The all-male themed parties, pool parties, clothing optional events, and adult-oriented entertainment promise to be HOT! https://gaykeywestfl.com/tropical-heat/
September 2027
September 1-5, 2027
Key West Womanfest – Festival highlights are to include themed and pool parties, live music shows and DJ sets, bike and trolley tours, gallery and arts events, a fabulous sunset sail, a clothing-optional snorkel trip, foodie experiences and more. https://gaykeywestfl.com/womenfest/
September 2-6, 2027
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
TBD
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/
October 2027
October 1-5, 2027
Key West Brewfest / octo-BREW-fest – Enjoy more than 60 vendors pouring 225-plus beers, from national craft names to Florida brewers, with an Oktoberfest feel. It is put on by the Key West Sunrise Rotary, and proceeds go back into local charities.
October 22-31, 2027
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.
November 2026
A great time of the year to visit. Fantastic dryer weather starts to move in. It’s our offseason so places to stay might be more affordable to enjoy some of our Key West events or just come and visit.
November 1-8, 2026
Key West World Championship Power Boat Races – https://raceworldoffshore.com/key-west/
November 14, 2026
Key West Oyster Fest – The inaugural Key West Oyster Fest takes place from 5pm – 10pm at the Half Shell Raw Bar, 231 Margaret Street. Keys Ambassador Chef Norman Van Aken, alongside presenters Half Shell Raw Bar, Everglades Oyster Company, and the Gulf Oyster Movement are putting on this event. Enjoy unlimited raw and fire-grilled local oysters until 8:00 PM from various regional farms and restaurant partners. A premium open bar featuring craft cocktails, beer, and wine runs until 8:00 PM before transitioning to a cash bar. Features live music from bands like The Farm Boys, live auctions, and supports local coastal reef restoration through oyster shell recycling.vailable for purchase online via Eventbrite.
December 2026
Dry cooler air prevails here in December. The beginning of the month is still slow season. Not too many Key West events but we have some pretty great places to Eat for Christmas dinner. Check out our Christmas Key West blog posts.
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!
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.