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
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...
Featured
Islamorada
Morada Way Third Thursday Art Walk
Nov 20, 2025, Dec 18, 2025, Jan 15, 2026, Feb 20, 2026, Mar 19, 2026, Apr 16, 2026, May 21, 2026, Jun 18, 2026, Jul 16, 2026, Aug 21, 2026, Sep 17, 2026, Oct 15, 2026
Dates: Third Thursday of each month from 6 to 9pm Experience the vibrant Morada Way Arts & Cultural District Art Walk in the Florida Keys! Enjoy local...
Featured
Key West
Ben Harrison at Key West Theater
Jan 8, 2026, Jan 21, 2026, Feb 5, 2026, Mar 5, 2026, Mar 25, 2026
Show Dates: Jan 8, 21 Feb 5, 17 March 5, 25 IRREVERENT, FUNNY, and FULL OF KEY WEST, Ben is the author of the musicals UNDYING LOVE, EL ISLEÑO: The...
Featured
Key West
AT THE WEDDING at Red Barn Theater
Jan 20, 2026, Jan 24, 2026, Jan 27, 2026, Jan 31, 2026, Feb 3, 2026, Feb 7, 2026, Feb 10, 2026, Feb 14, 2026
Jan 20 - Feb 14, 2026 Shows: Tuesdays-Saturdays at 7:30pm Patrons will be cordially invited to a Northern California wedding and meet Carlo, an agent...
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
Flourish: A Floral Arranging Experience with Hard Rock Cafe
Feb 14, 2026
Saturday, February 14, 1:00–3:00pm Spend your Valentine’s weekend getting creative at FLOURISH, a hands-on floral arranging experience at Hard Rock...
Key West
A Century of Romance Tasting Menu at Perla
Feb 14, 2026
In honor of Valentine’s Day, La Concha Key West, Autograph Collection invites couples to celebrate a love story 100 years in the making with their...
Key West
20th Annual Florida Keys Seafood Festival
Feb 14 - 15, 2026
Experience the vibrant flavors of the Florida Keys at the Seafood Festival! Enjoy fresh local seafood, live music, family-friendly activities, and...
Key West
A Tribute to The Songs of Pat Dailey w. Ray Fogg and Reese Dailey at Key West Theater
Feb 14, 2026
Ray Fogg and Reese Dailey will be teaming up to pay tribute to the songs of the legendary Pat Dailey. During his long career, Pat Dailey created an...
Key West
The Wearable Art Fashion Show at Hellings Curry Museum, home of the Key West Woman's Club
Feb 14, 2026
Experience the Wearable Art Fashion Show in Key West on Feb 14 at the Hellings Curry Museum: an afternoon runway of breathtaking, handcrafted garments...
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...
Key West
The Love Party: A New Play by Chantal Pavageaux
Feb 14, 2026
Celebrate Valentine’s Day with The Love Party, a lively and immersive new play by Chantal Pavageaux, presented by Queer Keys. Blending storytelling...
The Lower Keys
Run With Deer 5K Run/Walk
Feb 14, 2026
Join the 10th Annual Run With Deer 5K Run/Walk on Feb 14, 2026 at Big Pine Community Park, Big Pine Key. 8 AM start. Family-friendly, scenic island...
Key Largo
Sundowners: Dinner for Two
Feb 14, 2026
Celebrate love with an unforgettable Dinner for Two Prix Fixe at Sundowners, Key Largo. For $75 per couple, enjoy a thoughtfully curated multi-course...
