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
New Year's Eve Red Shoe Drop
Dec 31, 2025
Ring in the New Year, Key West-style, with one of the island’s most iconic and flamboyant celebrations — the Red Shoe Drop! As the clock counts down...
Featured
Key West
Key West Literary Seminar (2026)
Jan 8 - 11, 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...
Featured
Key West
Mile 0 Fest (2026)
Jan 27 - 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...
Islamorada
Cheeca Lodge & Spa Presidential Sailfish Tournament
Jan 23 - 25, 2026
The Cheeca Lodge Presidential Sailfish Tournament takes place January 23rd through 25th in Islamorada and serves as the final leg of the three...
Islamorada
Island Boat Show 2026
Jan 23 - 25, 2026
Experience the Island Boat Show in the beautiful Florida Keys! Explore top boat brands, enjoy waterfront views, live music, delicious food, and family...
Key West
The Young Dubliners: The HOT TODDY Tour at Key West Theater
Jan 23, 2026
Experience an unforgettable night in the Florida Keys! Catch The Young Dubliners live at the Key West Theater on January 23. Enjoy high-energy Celtic...
Key West
South Florida Symphony Orchestra: Sibelius’ Symphony No. 2 & Ravel’s Piano Concertoat Tennessee Williams Theater
Jan 24, 2026
Rhythmic drive meets lyrical beauty in this exhilarating South Florida Symphony program brimming with wit and brilliance when Ravel’s bluesy and...
The Lower Keys
22nd Annual Nautical Expo
Jan 24 - 25, 2026
The Lower Keys Chamber of Commerce welcomes you to one of our biggest events with over 100 vendors who showcase a variety of nautical items. Boating...
Key West
Paradise Big Band at Tennessee Williams Theater
Jan 25, 2026
Under the baton of Joe Dallas Jr, the band remains a truly "local" organization consisting of professional and semi-professional musicians from the...
Featured
Key West
The Yuck Show: The Science of Slime in Key West! at Tennessee Williams Theater
Jan 27, 2026
Experience The Yuck Show: The Science of Slime at Key West’s Tennessee Williams Theatre! Perfect for families and curious minds, this interactive...
Key West
Food and Wine Festival Key West
Jan 28 - Feb 1, 2026
Experience the Key West Food & Wine Festival in the beautiful Florida Keys! Savor world-class cuisine, fine wines, and vibrant island culture with...
Key West
King Master
Jan 28 - 31, 2026
Experience the thrill of the ultimate King Master fishing event in the stunning Florida Keys, where turquoise waters meet endless adventure. Set...
Featured
Key West
Waterfront Playhouse - Almost, Maine (Mainstage Series)
Jan 29, 2026, Jan 30, 2026, Jan 31, 2026, Feb 1, 2026, Feb 2, 2026, Feb 3, 2026, Feb 4, 2026, Feb 5, 2026, Feb 6, 2026, Feb 7, 2026, Feb 8, 2026, Feb 9, 2026, Feb 10, 2026, Feb 11, 2026, Feb 12, 2026, Feb 13, 2026, Feb 14, 2026
Jan 29, 2026 - Feb 14, 2026 This whimsical and heartfelt series of vignettes explores the joys and sorrows of love in a mythical town in northern...
Key West
Scott Kirby- 35 Years of Songs & Stories w/ Lew London at Key West Theater
Jan 29, 2026
Singer, songwriter, guitarist, storyteller, traveler and road warrior are all words that aptly describe Scott Kirby. Finishing songs while driving...
Key West
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...
Key West
Key West Tropical Forest & Botanical Garden turns 90
Jan 30, 2026
Discover paradise at the Key West Tropical Forest & Botanical Garden! Explore lush trails, vibrant native plants, and unique wildlife in the heart of...
Key West
Key West Tropical Forest & Botanical Garden Petals & Pearls
Jan 30, 2026
Join us for Petals & Pearls, an elegant evening celebrating the 90th anniversary of the Key West Tropical Forest & Botanical Garden, fondly known as...
Islamorada
Swamp Guides Ball
Jan 30 - 31, 2026
The Swamp Guides Ball returns bringing together anglers of all experience levels for a fun-filled, all-release backcountry fishing tournament...
