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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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...
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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...
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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...
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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...
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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
Libby York Our Love is Here to Stay at The Studios of Key West
Feb 11, 2026
Treat yourself to a romantic Florida Keys night: acclaimed vocalist Libby York with Chicago pianist Tom Vaitsas, Geoff Lowe (bass) and Mark Rose (sax)...
Key West
Paint Pouring with Sandy West
Feb 11, 2026
Dive into the vibrant world of acrylic paint pouring in this hands-on class led by Sandy West. Open to all experience levels, the session explores...
Islamorada
Cubans in the Keys Lecture at the Florida Keys History & Discovery Center
Feb 11, 2026
Discover the deep ties between Cuba and the Florida Keys in "Cubans in the Keys," a lively lecture with Dr. Heather Gonyeau at the Florida Keys...
Key West
Mat Pilates with Betina Justice
Feb 11, 2026
Escape to Key West for a rejuvenating Mat Pilates class with Betina Justice at Williams Hall. In this 45-minute mat-based session (Feb 11, 11:30 AM)...
Key West
Put-in-Bay Days in Key West 2026
Feb 11 - 15, 2026
Put‑in‑Bay Days in Key West, Feb 11–15, 2026: five days and 100+ hours of live music as Put‑in‑Bay favorites—Ray Fogg, Reese Dailey, Pat Shepard, Kari...
Key West
Swing, Latin & Ballroom Dancing with Lucy Carleton
Feb 12, 2026
Join Lucy Carleton in Key West for an energetic hour of Swing, Latin & Ballroom dancing at Williams Hall (Feb 12, 5–6pm). All levels welcome—no...
Key West
Happy Hour at Harry's
Feb 12, 2026
Celebrate Key West history at Happy Hour at Harry’s on Feb 12, 2026, 6–8pm at the Truman Little White House. Sip beer, wine or a specialty bourbon...
Key West
LOL Essential Oils: Blending & Bracelet-Making
Feb 12, 2026
Explore scent and self-expression in this relaxing, hands-on workshop led by **Karen Moore**. Open to all levels, the class introduces participants to...
Key West
Scott Kirby- 35 Years of Songs & Stories w/ Mike Michaels at Key West Theater
Feb 12 - 13, 2026
Singer, songwriter, guitarist, storyteller, traveler and road warrior are all words that aptly describe Scott Kirby. Finishing songs while driving...
Key West
First Look Staged Reading series at The Studios - The Patrons by Nicholas Gandiello Directed by Aaron Rossini
Feb 13 - 14, 2026
"The Patrons" — a gripping staged reading by Nicholas Gandiello (dir. Aaron Rossini). Set in 1963, library staff clash over a controversial book and...
Key West
Pilobolus at Tennessee Williams Theater
Feb 13, 2026
Pilobolus’s Other Worlds Collection traverses the spaces we inhabit—from the realms within ourselves, society, and the universe—with wit, wisdom, and...
