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
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...
Featured
Key West
Distinguished Speaker Series: Elizabeth Bishop | A Poet of the Shorelines
Feb 5, 2026
Experience Key West’s literary side at KWAHS’s Distinguished Speaker Series: "Elizabeth Bishop — A Poet of the Shorelines" on Feb 5 at Tropic Cinema...
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
Marathon
The Odd Couple at Marathon Community Theater
Jan 8, 2026, Jan 9, 2026, Jan 10, 2026, Jan 15, 2026, Jan 16, 2026, Jan 17, 2026, Jan 22, 2026, Jan 23, 2026, Jan 24, 2026, Jan 25, 2026, Jan 29, 2026, Jan 30, 2026, Jan 31, 2026
JANUARY 8, 9, 10 @ 8:00PM JANUARY 15, 16, 17 @ 8:00 PM JANUARY 18 @ 3:00 PM-SUNDAY MATINEE JANUARY 22, 23, 24 @ 8:00PM JANUARY 25 @ 3:00PM -SUNDAY...
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
70 Girls 70 at Fringe Theater
Jan 21, 2026, Jan 22, 2026, Jan 23, 2026, Jan 24, 2026, Jan 25, 2026, Jan 26, 2026, Jan 27, 2026, Jan 28, 2026, Jan 29, 2026, Jan 30, 2026, Jan 31, 2026
Jan 21 - Jan 31 Don’t miss the concert-style revival of 70 Girls 70, the delightfully irreverent Kander & Ebb musical running January 21–31. This...
The Lower Keys
Paddle for Paws
Jan 24, 2026
Major Norman D. Belson Paddle for Paws — enjoy a leisurely kayak or paddleboard around scenic Cudjoe Key on Jan 24, then celebrate at Bent Prop with...
Islamorada
History of Diving Museum Guided Tours
Jan 24, 2026
Explore the History of Diving Museum in Islamorada — an immersive, family-friendly dive into underwater exploration. View vintage gear, rare artifacts...
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...
The Lower Keys
CONNECTIONS PROJECT Pop-Up - Nautical Market, Lower Keys Chamber
Jan 24, 2026
Join The Connections Project: A Mosaic of the Keys— pop-up event across the Florida Keys celebrating local visual and performing artists. Explore...
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...
Key West
Peytan Porter Live! at the Key West Listening Room
Jan 25, 2026
Peytan Porter takes the stage at the historic Key West Theater for an exciting live performance that showcases her bold blend of country, indie-pop...
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...
Key West
Andrew Duhon at Key West Theater
Jan 26, 2026
Andrew Duhon brings his evocative storytelling and rich musical blend of folk, blues, and Americana to the intimate Backstage Listening Room at the...
Key West
Library Speaker Series: Sarah Stewart Taylor
Jan 26, 2026
Join bestselling mystery author Sarah Stewart Taylor at Key West Library on Jan 26, 6:00 PM for a free Speaker Series talk. Creator of the Sweeney St...
Marathon
Kouzov Duo at Marathon High School PAC
Jan 26, 2026
Experience an elegant evening in the Florida Keys: the Kouzov Duo—prize‑winning cellist Dmitry Kouzov and pianist Yulia Federoseeva Kousova—perform...
