Events
It's not just another day in paradise! You'll find doings and happenings up and down the Keys, nearly every day of the year. Check out the latest fun and frolic below.
Only-In-The-Keys Festivals & Events
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.
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Featured
Key West
Key West Pride 2026
Jun 3 - 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...
Featured
Islamorada
REEF Fish out of Water 5K
Jun 7, 2026, Jun 8, 2026, Jun 9, 2026, Jun 10, 2026, Jun 11, 2026, Jun 12, 2026, Jun 13, 2026
June 7–13, 2026 The REEF Fish Out of Water Virtual 5K is a global, community-driven event that brings ocean lovers together to support marine...
Key West
Summer Solstice Celebration
Jun 8 - 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! Enjoy live...
Key West
Steve Earle - Solo & Acoustic at Key West Theater
Jun 9, 2026
Experience GRAMMY-winning Americana legend Steve Earle—solo & acoustic—at Key West Theater (512 Eaton St) on June 9, 2026. An intimate island-night of...
Islamorada
Ladies Tarpon Fly Tournament
Jun 9 - 11, 2026
The Ladies Tarpon Fly Tournament is a long-running invitational fly-fishing tournament celebrating women in saltwater angling in the Florida Keys...
Key West
CFK Swim Around Key West & Swim Meets
Jun 12 - 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...
Islamorada
Ladies Dolphin Tournament of the Florida Keys (2026)
Jun 12 - 13, 2026
It’s time for ladies to grab their rods, rally their crew, and get ready for some friendly, competitive fishing with a purpose. Hosted by the Florida...
Key West
Sun Stories: Memory & Light in Key West with Eszter Sziksz (PEAR)
Jun 12, 2026
Reflect on your personal connection to place in this contemplative, hands-on workshop with artist Eszter Sziksz. Beginning with a guided discussion on...
Key West
Annual Dagger Dive & TLWH Community Event
Jun 13 - 21, 2026
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...
Key West
Truman’s Tropical Fruit Festival
Jun 13, 2026
Join Truman’s Tropical Fruit Festival in Key West on Saturday, June 13, 2026, 9 AM–noon at the Harry S. Truman Little White House. Free admission...
Marathon
City of Marathon Presents: Hot Havana Nights
Jun 13, 2026
Experience a lively evening of Latin music, dancing, and tropical fun at Hot Havana Nights in Marathon. Set along the waterfront, this festive event...
Key Largo
MarineLab Family Day: Invertebrate Diversity at Rodriguez Key
Jun 14, 2026
Join us for a family-friendly trip to Rodriguez Key to explore the amazing diversity of marine invertebrates! Snorkel the shallow waters around this...
Islamorada
63rd Annual Gold Cup Tarpon Tournament
Jun 15 - 19, 2026
Gold Cup Tarpon Tournament returns to Islamorada June 15–19, 2026, marking the 63rd anniversary of one of the world’s most prestigious fly-fishing...
Featured
Key West
Myth and Material with Wendell Smith (PEAR)
Jun 15, 2026, Jun 16, 2026
Monday & Tuesday, June 15 & 16, 11am – 3pm Explore mythology as a powerful source of creative inspiration in this interdisciplinary workshop with...
Key West
Science Fiction in Theatre with Gordon Dahlquist (PEAR)
Jun 17, 2026
Explore how speculative worlds come to life on stage in this imaginative workshop with playwright and novelist Gordon Dahlquist. Drawing inspiration...
Featured
Key West
Tom Arnold at Comedy Key West
Jun 18 - 19, 2026, Jun 19 - 20, 2026, Jun 20, 2026
June 18, 19, 20 Tom Arnold brings three nights of big laughs to Comedy Key West, June 18 through 20. An actor, writer, and stand-up comedian with a...
