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
Key West
New Year's Eve Red Shoe Drop
Dec 31, 2025
Ring in the New Year, Key West-style, with one of the island’s most iconic and flamboyant celebrations — the Red Shoe Drop! As the clock counts down...
Featured
Key West
Key West Literary Seminar (2026)
Jan 2 - 12, 2026
The Key West Literary Seminar is a world-renowned annual event that celebrates the art of storytelling in one of the most inspiring literary...
Key West
Schooner Wharf "Rigging" in the New Year!
Dec 31, 2025
Ring in the New Year at the iconic Lowering of the Pirate Wench at Schooner Wharf Bar in Key West! Join the lively crowd at midnight as a pirate wench...
Key West
Polve Vault in Paradise (2026)
Jan 1 - 4, 2026
Experience Pole Vault in Paradise in Key West! Join us for an exciting pole vault competition set against stunning island views. Enjoy a unique blend...
Featured
Key West
Waterfront Playhouse - What the Constitution Means to Me (Spotlight Series)
Jan 1, 2026, Jan 2, 2026, Jan 3, 2026
Jan 1, 2026 - Jan 3, 2026 Fifteen-year-old Heidi earned her college tuition by winning constitutional debate competitions across the country. In this...
Key West
Scott Kirby- 35 Years of Songs & Stories w/ Noah Robertson at Key West Theater
Jan 2 - 3, 2026
Jan 2 & Jan 3 Singer, songwriter, guitarist, storyteller, traveler and road warrior are all words that aptly describe Scott Kirby. Finishing songs...
Key Largo
Orange Bowl Swim Classic
Jan 3, 2026
The Orange Bowl Swim Classic is held the first weekend in January and is an integral part of the Orange Bowl events schedule. Jacobs Aquatic Center...
Key West
Ulysses Quartet at Tennessee Williams Theater
Jan 4, 2026
The Ulysses Quartet has been praised for their "textural versatility," "grave beauty" and "the kind of chemistry many quartets long for, but rarely...
Key West
Rams Head Presents: Los Lobos
Jan 6, 2026
Experience an unforgettable night in the Florida Keys as Rams Head Presents Los Lobos! Enjoy the legendary band’s unique blend of rock, blues, and...
Key West
Schmaltz & Pepper at Tennessee Williams Theater
Jan 6, 2026
Classy klezmer- chamber music and jazz infused with schmaltz A uniquely virtuosic and entertaining chamber ensemble performing original music inspired...
Key West
THE QUEENS OF COUNTRY: PATSY! DOLLY! LORETTA!
Jan 7 - 10, 2026
Christine Mild will return to the Barn with her latest musical special event, “The Queens of Country: Patsy! Dolly! Loretta!”. The show will have only...
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...
Marathon
Women of Wing Clinic
Jan 8 - 11, 2026
Escape to the Florida Keys for a transformative Women of Wing retreat! Enjoy sun-soaked days, wellness workshops, inspiring connections, and...
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...
Key West
RAMS HEAD PRESENTS: ROBYN SCHALL'S HOLIDAY EXTRAVAGANZA TOUR
Jan 9, 2026
Experience holiday magic in the Florida Keys! Don’t miss Robyn Schall’s Holiday Extravaganza at the Key West Theater on Janurary 9. Enjoy an evening...
Islamorada
Fish for Holly Sailfish Tournament (2026)
Jan 9 - 11, 2026
Every donation you make, every act of generosity, becomes a part of Holly's legacy. By supporting The Holly Given Fund, you're not just contributing...
Key West
Analogous: Old Cameras. New Work. An Experiment in Analog Photography by Key West Artists Michael Marrero and Mark Hedden
Jan 9, 2026
Exhibit Runs January 9, 2026 - February 15, 2026 Analogous Old Cameras. New Work. An Experiment in Analog Photography by Key West Artists Michael...
