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.
See Some Shenanigans
34th Annual Florida Keys Island Fest
Each spring, the Florida Keys Island Fest brings two days of vibrant community celebration to Founders Park in Islamorada. Organized by the Islamorada...
Valentine's Day Dinner at Four Flamingos
Celebrate love with an unforgettable waterfront Valentine’s Day dinner at Four Flamingos, A Richard Blais Key West Kitchen. Join us on Saturday...
Presidential Families Weekend Forum
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...
Wesley House Valentine's Gala
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...
New Year, New Style Jewelry Pop-up Shop
Sun Feb 15, 10–4: ZEN by Karen Moore at The Perry Hotel, Stock Island. Complimentary gem consultations, layering tips, and handmade ocean-inspired...
Horszowski Trio at Tennessee Williams Theater
Impromptu Classical Concerts Giving performances that are “lithe, persuasive” (The New York Times), “eloquent and enthralling” (The Boston Globe), and...
RAMS HEAD PRESENTS: GABRIEL RUTLEDGE: DON'T READ THE COMMENTS TOUR
A past winner of both the Seattle International Comedy Competition and The Laughing Skull Comedy Festival in Atlanta, Gabriel has made numerous...
Spotlight Series: Sarah's Oil at Tropic Cinema
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...
You Are What You Collect: The Slightly Surreal World of Konstantin Bessmertny
Step into an intimate and thought-provoking evening celebrating the art and ideas of Konstantin Bessmertny. Hosted by Jon and Eliza Lewis **in their...
Empress Gin Cocktail Contest with Andy Westcott Band LIVE
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...
SOMO Roots
SoMo Roots takes over Southernmost Beach Resort in Key West for a beachfront night of live music, tropical cocktails, and spectacular sunset views...
Rising Star Concert– Sophia Liu, (Piano) at Marathon High School PAC
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...
Non-Profit Bingo Night at Green Parrot
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...
Library Speaker Series: Mirta Ojito
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...
Billy Stritch and Gabrielle Stravelli Spotlight Cabaret curated by Randy Roberts at The Studios of Key West
Enjoy an elegant Key West evening as pianist-singer Billy Stritch and jazz vocalist Gabrielle Stravelli present "Mel and Ella Swing!"—an intimate...
Presidents' Day Cookout
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...