2026 Events & Festivals
Waterfront Playhouse – What the Constitution Means to Me (Spotlight Series)
Jan 1, 2026 – Jan 3, 2026 Fifteen-year-old Heidi earned her college tuition by winning constitutional debate competitions across the country. In this critically acclaimed and deeply personal play, she resurrects her teenage self to examine how our founding document has shaped generations of American women. “Not just the best play to open on Broadway this season, but also the most important.” – The New York Times
https://www.waterfrontplayhouse.org/shows/what-the-constitution-means-to-me/#/productions-view
Pole Vault in Paradise
Jan 1, 2026 – Jan 4, 2026
Experience Pole Vault in Paradise in Key West! Join us for an exciting pole vault competition set against stunning island views. Enjoy a unique blend of athleticism and tropical fun—perfect for athletes, families, and spectators. Don’t miss this unforgettable event in the Florida Keys!
https://runsignup.com/Race/FL/KeyWest/PoleVaultInParadise
THE QUEENS OF COUNTRY: PATSY! DOLLY! LORETTA!
Jan 7, 2026 – Jan 10, 2026
Christine Mild will return to the Barn with her latest musical special event, “The Queens of Country: Patsy! Dolly! Loretta!”. The show will have only four performances, January 7-10, 2026. Pianist Jim Rice will once again lead a terrific country band to back Christine up. Limited tickets will be available, and Christine always sells out, so grab your seats as soon as they go on sale later this summer.
https://redbarntheatre.com/shows/the-queens-of-country-patsy-dolly-loretta
RAMS HEAD PRESENTS: GIVEN TO FLY: A TRIBUTE TO PEARL JAM
Jan 10, 2026
Given to Fly recreates the power and passion of Pearl Jam’s iconic sound and live show. Fronted by Bob Donahue, with his rich and resonant voice that’s strikingly similar to Eddie Vedder’s, Given to Fly is made up of talented, veteran musicians that deliver the vibe, energy, and electricity of Pearl Jam… on classic hits, deep cuts, and new material. Given to Fly is a Pearl Jam tribute for Pearl Jam’s most die-hard fans.
https://thekeywesttheater.com/
5th Annual Key West Chick Fest
Jan 14, 2026 – Jan 18, 2026
Join the ultimate girls’ getaway at Key West Chick Fest, January 14-18, 2026! Enjoy live music, beach parties, island adventures, and exclusive events with Erica Sunshine Lee. Experience the vibrant spirit of the Florida Keys—sun, fun, and unforgettable memories await!
https://www.ericasunshinelee.com/keywestchickfest
Key West Literary Seminar
Jan 2, 2026 – Jan 12, 2026
The Key West Literary Seminar is a world-renowned annual event that celebrates the art of storytelling in one of the most inspiring literary destinations in the world. Each January, authors, poets, journalists, playwrights, and passionate readers gather in Key West to share ideas, explore literary themes, and honor the island’s long tradition as a creative haven for writers.
https://www.kwls.org/
Jimmy Buffett’s Coral Reefer Band
Jan 16, 2026
Jimmy Buffett’s Coral Reefer Band – Keepin’ the Party Going For over five decades, Jimmy Buffett and The Coral Reefer Band created the soundtrack to endless summers, salty breezes, and carefree good times. What began in 1973, evolved into one of the most beloved live acts in American music history. Though the legendary Jimmy Buffett passed away in 2023, he left a clear message to“keep the party going.” And that’s exactly what The Coral Reefer Band continues to do—with their heart and soul.
https://www.thekeywestamp.com/events/detail/jimmy-buffetts-coral-reefer-band
Southernmost Youth Regatta
Jan 16, 2026 – Jan 18, 2026
The Southernmost Youth Regatta, held January 16–18, 2025, is the youth component of the renowned Southernmost Regatta — a weeklong celebration of competitive sailing in Key West, Florida.
https://www.regattanetwork.com/event/30153
28th Annual Key West Half Marathon & Runfest
Jan 17, 2026 – Jan 18, 2026
Experience the excitement of the Key West Half Marathon! Run through stunning oceanfront views, lively streets, and historic landmarks in the heart of the Florida Keys. Enjoy live music, local food, and a festive island atmosphere—perfect for leisure travelers seeking fun and adventure.
https://keywesthalfmarathon.com/
The Southernmost Regatta
Jan 19, 2026 – Jan 24, 2026
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/
Kelly McGillis Classic
Jan 20, 2026 – Jan 26, 2026
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/
King Master
Jan 28, 2026 – Jan 31, 2026
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/
Mile 0 Fest
Jan 27, 2026 – Jan 31, 2026
Experience Mile 0 Fest in the stunning Florida Keys! 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.
https://www.mile0fest.com/
Petals and Pearls Gala
Jan 30, 2026
Celebrate the 90th Anniversary Gala at Key West Garden Club’s “Petals & Pearls” event! Enjoy an enchanting evening of live music, gourmet cuisine, and lush tropical beauty in the historic West Martello Tower. Experience the magic of the Florida Keys—an unforgettable night awaits!
https://www.keywest.garden/petals-pearls-90th-anniversary-gala/
20th Annual Florida Keys Seafood Festival
Feb 14, 2026 – Feb 15, 2026
Experience the vibrant flavors of the Florida Keys at the Seafood Festival! Enjoy fresh local seafood, live music, family-friendly activities, and unique island crafts. Savor the best of the Keys’ culinary traditions and coastal culture in a lively, festive atmosphere. Don’t miss out!
https://floridakeysseafoodfestival.com/
Key West Art & Craft Festival
Feb 21, 2026 – Feb 22, 2026
Experience the vibrant art scene of the Florida Keys at the Key West Art Center! Discover stunning local artwork, meet talented artists, and enjoy a unique cultural event in a beautiful historic setting. Perfect for leisure travelers seeking inspiration and authentic island charm.
https://keywestartcenter.com/
The Man In Black: A Tribute to Johnny Cash at Key West Theater
Mar 5, 2026
With his strikingly similar looks, baritone voice, and spot-on mannerisms, Shawn Barker’s uncanny resemblance to the original “Man In Black” revitalizes the true character and spirit of Mr. Cash himself, one of America’s greatest musical icons, for a truly one-of-a-kind show. The energetic show features Barker in character throughout the entire evening, walking the audience through each era of Cash’s life and music.
https://thekeywesttheater.com/
Conch Shell Blowing Contest
Mar 7, 2026
The Conch Shell Blowing Contest celebrates a cherished Florida Keys tradition with a blend of history and creativity. Hosted in the lush garden of the Oldest House at 322 Duval Street, this free event welcomes participants of all ages to display their conch-blowing skills.
https://oirf.org/
March Merkin
Mar 9, 2026 – Mar 12, 2026
Experience the thrill of fly fishing in the stunning Florida Keys at the March Merkin Invitational! Join fellow anglers for world-class permit fishing, camaraderie, and breathtaking scenery. Don’t miss this unique event—cast your line and create unforgettable memories in paradise!
https://marchmerkin.com/
Taste of Key West
Mar 23, 2026
Experience the vibrant flavors of the Florida Keys at Taste of Key West! Savor delicious local cuisine, fine wines, and craft beers from top area restaurants, all set against stunning waterfront views. Join us for an unforgettable evening of food, fun, and island hospitality!
https://tasteofkeywest.org/
Key West Sailfish Tournament
Mar 26, 2026 – Mar 28, 2026
Experience the excitement of the Key West Sailfish Tournament in the beautiful Florida Keys! Join fellow anglers for thrilling offshore fishing, lively events, and a chance to win big prizes. Enjoy the vibrant Key West atmosphere, stunning ocean views, and unforgettable memories. Don’t miss out!
https://keywestsailfishtournament.com/
Spanish Fly Shark Tournament
Apr 2, 2026 – Apr 4, 2026
Experience the thrill of the Key West Shark Tournament in the beautiful Florida Keys! Join fellow anglers for exciting shark fishing, cash prizes, and unforgettable ocean adventures. Enjoy lively events, local hospitality, and the chance to reel in the catch of a lifetime. Don’t miss out!
https://keywestsharktournament.com/
Conch Republic Independence Celebration
Apr 17, 2026 – Apr 26, 2026
Experience the quirky spirit of the Conch Republic in the Florida Keys! Join us for lively parades, local music, delicious seafood, and unforgettable island fun. Celebrate independence, creativity, and community in a tropical paradise where every day feels like a festival. Don’t miss out!
https://conchrepublic.com/
Cuban Art Tours
Apr 20, 2026 – Apr 24, 2026
Experience “Havana 2025” at Gallery on Greene in the Florida Keys! Immerse yourself in vibrant Cuban art, culture, and music. Discover stunning works by renowned artists, enjoy lively performances, and savor the spirit of Havana—right in the heart of Key West. Don’t miss this unique event!
https://galleryongreene.com/havana-2025
Foreigner at Coffee Butler Amphitheater
Apr 23, 2026
Get ready for an unforgettable night of classic rock as Foreigner brings their All Songs From The Classic Album & Other Hits tour to the Coffee Butler Amphitheater on Thursday, April 23, 2026. The legendary band will be joined by special guest and original lead singer Lou Gramm, reuniting fans with one of rock’s most iconic voices. Fans will be treated to powerhouse performances of timeless hits including “Juke Box Hero,” “Waiting for a Girl Like You,” “Urgent,” “Night Life,” “Hot Blooded,” “Cold as Ice,” “Feels Like the First Time,” and the chart-topping ballad “I Want to Know What Love Is.”
https://thekeywestamp.com/
Key West Songwriters Festival
Apr 29, 2026 – May 3, 2026
The Key West Songwriters Festival is 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. Anchored in the heart of the Florida Keys, the festival spans intimate venues, waterfront stages, bars, theatres, and even sunset sails — delivering a unique island experience where the voices behind your favorite songs take center stage.
https://keywestsongwritersfestival.com/
Key West Paddle Classic
May 7, 2026 – May 10, 2026
Experience the thrill of the Key West Paddle Classic in the stunning Florida Keys! Join fellow paddlers for an unforgettable race around Key West, surrounded by turquoise waters and vibrant island energy. Whether you’re a competitor or a spectator, it’s a must-attend event for adventure lovers!
https://www.floridakeyswatermancompany.com/keywestpaddleclassic
Key West Pride 2026
Jun 3, 2026 – Jun 7, 2026
Every June, Key West Pride turns the island into a vibrant, inclusive festival full of color, community, and celebration. 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.
https://gaykeywestfl.com/pride/
Summer Solstice Celebration
Jun 8, 2026 – Jun 21, 2026
Join us at Mallory Square for the annual Summer Solstice Celebration—a vibrant, nightly festival leading up to the longest day of the year!
CFK Swim Around Key West & Swim Meets
Jun 12, 2026 – Jun 14, 2026
Dive into adventure at the Swim Around Key West! Experience the thrill of a 12.5-mile open-water swim in the stunning turquoise waters of the Florida Keys. Whether you’re a seasoned swimmer or a passionate spectator, enjoy vibrant island vibes, breathtaking views, and unforgettable memories.
https://swimaroundkeywest.org/
Key Lime Festival
Jul 1, 2026 – Jul 5, 2026
The Key Lime Festival is a vibrant, multi-day celebration held each summer in Key West, Florida, honoring the island’s signature citrus and quirky spirit. From July 1–5 (2026), 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/
Hemingway Days & Hemingway Look-Alike Contest
Jul 19, 2026 – Jul 26, 2026
Key West comes alive with Hemingway Days, a spirited five-day festival celebrating the life, legacy, and island era 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.
https://hemingwaydays.com/
Key West Marlin Tournament
Jul 22, 2026 – Jul 25, 2026
Experience the thrill of world-class sportfishing at the Key West Marlin Tournament! Join us in the Florida Keys for exciting competition, cash prizes, and unforgettable ocean adventures. Enjoy vibrant nightlife, stunning sunsets, and the unique charm of Key West. Don’t miss out!
https://keywestmarlin.com/
Hemingway 5K Sunset Run & Beer Mile
Jul 24, 2026 – Jul 26, 2026
Experience the excitement of the Key West Half Marathon! Run through stunning oceanfront views, lively streets, and historic landmarks in the heart of the Florida Keys. Enjoy live music, local food, and a festive atmosphere!
https://keywesthalfmarathon.com/
28th Annual Key West Lobsterfest
Aug 5, 2026 – Aug 9, 2026
Dive into the ultimate seafood celebration at Key West Lobsterfest! Enjoy fresh lobster, vibrant street parties, live music, and delicious local flavors in the heart of the Florida Keys. Don’t miss this unforgettable summer event—perfect for foodies and fun-seekers alike!
https://keywestlobsterfest.com/
Womensfest Key West
Sep 2, 2026 – Sep 6, 2026
Experience Womenfest in Key West, the ultimate celebration for women in paradise! Enjoy pool parties, live entertainment, water adventures, and vibrant nightlife in a welcoming, inclusive atmosphere.
https://gaykeywestfl.com/womenfest/
Just a Few Friends Key West
Sep 3, 2026 – Sep 7, 2026
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/
CFK Pentathlon Swim Meet & Key West Open Water Swim
Sep 5, 2026 – Sep 6, 2026
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/
Fantasy Fest
Oct 16, 2026 – Oct 25, 2026
Fantasy Fest is an electrifying, 10-day costume and performance festival held annually in Key West, Florida, each October.
https://fantasyfest.com/schedule/
Rigging in the New Year
Dec 31, 2026
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.
https://schoonerwharf.com/