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
Islamorada
34th Annual Florida Keys Island Fest
Mar 28 - 29, 2026
Each spring, the Florida Keys Island Fest brings two days of vibrant community celebration to Founders Park in Islamorada. Organized by the Islamorada...
Key West
Valentine's Day Dinner at Four Flamingos
Feb 14, 2026
Celebrate love with an unforgettable waterfront Valentine’s Day dinner at Four Flamingos, A Richard Blais Key West Kitchen. Join us on Saturday...
Key West
Presidential Families Weekend Forum
Feb 14, 2026
Join Presidential Families Weekend in Key West—Feb 14 at the Harry S. Truman Little White House—for "The Legacy of President Carter." Meet Amy Carter...
Key Largo
Wesley House Valentine's Gala
Feb 14, 2026
Celebrate Valentine’s Night in Key Largo at the 3rd Annual Wesley House Valentine’s Gala on Feb 14, 6–10 PM. Enjoy Keys-formal ambiance, champagne, a...
The Lower Keys
New Year, New Style Jewelry Pop-up Shop
Feb 15, 2026
Sun Feb 15, 10–4: ZEN by Karen Moore at The Perry Hotel, Stock Island. Complimentary gem consultations, layering tips, and handmade ocean-inspired...
Key West
Horszowski Trio at Tennessee Williams Theater
Feb 15, 2026
Impromptu Classical Concerts Giving performances that are “lithe, persuasive” (The New York Times), “eloquent and enthralling” (The Boston Globe), and...
Key West
RAMS HEAD PRESENTS: GABRIEL RUTLEDGE: DON'T READ THE COMMENTS TOUR
Feb 15, 2026
A past winner of both the Seattle International Comedy Competition and The Laughing Skull Comedy Festival in Atlanta, Gabriel has made numerous...
Key West
Spotlight Series: Sarah's Oil at Tropic Cinema
Feb 15, 2026
Escape to Key West for Tropic Cinema’s Spotlight screening of Sarah’s Oil — a quiet, powerful drama about a Black community rallying to save a family...
Key West
You Are What You Collect: The Slightly Surreal World of Konstantin Bessmertny
Feb 15, 2026
Step into an intimate and thought-provoking evening celebrating the art and ideas of Konstantin Bessmertny. Hosted by Jon and Eliza Lewis **in their...
Key West
Empress Gin Cocktail Contest with Andy Westcott Band LIVE
Feb 15, 2026
Get ready for a fun afternoon of cocktails and live music at the Empress Gin Cocktail Contest with Andy Westcott Band LIVE at The Marker Key West...
Key West
SOMO Roots
Feb 15, 2026
SoMo Roots takes over Southernmost Beach Resort in Key West for a beachfront night of live music, tropical cocktails, and spectacular sunset views...
Marathon
Rising Star Concert– Sophia Liu, (Piano) at Marathon High School PAC
Feb 16, 2026
Join rising-star pianist Sophia Liu in Marathon on Feb 16, 2026 at Marathon High PAC for the Jim Platt Memorial Concert — a dazzling program from...
Key West
Non-Profit Bingo Night at Green Parrot
Feb 16, 2026
Get ready for a fun night of games, prizes, and good times at Bingo at The Green Parrot! Join the Key West Art & Historical Society for a lively...
Key West
Library Speaker Series: Mirta Ojito
Feb 16, 2026
Join acclaimed journalist and author Mirta Ojito for a free Speaker Series talk at Key West Library on Feb 16, 2026 at 6:00 PM. A Pulitzer contributor...
Key West
Billy Stritch and Gabrielle Stravelli Spotlight Cabaret curated by Randy Roberts at The Studios of Key West
Feb 16, 2026
Enjoy an elegant Key West evening as pianist-singer Billy Stritch and jazz vocalist Gabrielle Stravelli present "Mel and Ella Swing!"—an intimate...
Key West
Presidents' Day Cookout
Feb 16, 2026
Join a festive, patriotic cookout on the historic Truman Little White House lawn in Key West — Monday, Feb 16, 2026, 11:30 AM–1:30 PM. Free and open...
