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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Key West
Key West Pride 2026
Jun 3 - 7, 2026
Every June, Key West Pride turns the island into a vibrant, inclusive festival full of color, community, and celebration. This weeklong event welcomes...
Key West
2nd Annual Key West Minster Dog Show hosted by DJ Sanaris
Apr 4, 2026
The 2nd Annual Key West Minster Dog Show returns on Saturday, April 4, 2026, from 11 AM to 3 PM at Sunset Pier, benefiting the Florida Keys SPCA...
Key West
Ruben Alpizar: Inhabiting the Absurd
Apr 4, 2026
Experience a compelling evening of art at The Gallery on Greene with Inhabiting the Absurd by Ruben Alpizar, an exhibition that invites viewers to...
Featured
Key West
Lighting the Fire to Write with Cricket Desmarais
Apr 5, 2026, Apr 12, 2026, Apr 19, 2026, Apr 26, 2026
April 5, April 12, April 19, April 26 Reignite your creativity in this welcoming Sunday morning writing series led by local writer and poet Cricket...
Key West
Puppy Pals, Live! at Tennessee Williams Theater
Apr 6, 2026
Part of the new Family Fun Series, which is designed to bring engaging and exciting performances for audiences of all ages to the Key West community...
Key West
RAMS HEAD PRESENTS: Crystal Gayle
Apr 7, 2026
Crystal Gayle brings her legendary voice and timeless songs to the Key West Theater for an unforgettable live performance. A Grammy Award–winning...
Key West
Mike Wiley at the American Legion Post 168
Apr 8 - 9, 2026
Mike Wiley brings Tired Souls: King and the Montgomery Bus Boycott and Breach of Peace to Key West—powerful solo performances exploring pivotal...
Key West
Coastline Exhibition Opening Reception at Jag Gallery
Apr 8, 2026
Celebrate the opening of Coastline, a collaborative exhibition by Adam Russell and Kelly Lever, at Jag Gallery in Key West. This highly anticipated...
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Key West
Steve Rannazzisi at Comedy Key West
Apr 8 - 11, 2026, Apr 9 - 12, 2026, Apr 10 - 13, 2026, Apr 11 - 14, 2026
April 8, 9, 10 & 11, 2026 Get ready for four nights of nonstop laughs with Steve Rannazzisi at Comedy Key West! Known for his quick wit, sharp...
Key West
Key West International Dance Company - "DARK NIGHT OF THE SOUL"
Apr 9 - 11, 2026
April 9, 10, 11, 15, 16, 17, 18, 22, 23, 24, 25 This is a rock ballet set to extraordinary music by Dan Krysa, set in 16th Century Spain. It tells the...
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Key West
Waterfront Playhouse - Accomplice (Mainstage Series)
Apr 9, 2026, Apr 10, 2026, Apr 11, 2026, Apr 12, 2026, Apr 13, 2026, Apr 14, 2026, Apr 15, 2026, Apr 16, 2026, Apr 17, 2026, Apr 18, 2026, Apr 19, 2026
Apr 9, 2026 - Apr 18, 2026 A deliciously twisted comic thriller by Tony Award winner Rupert Holmes. Winner of the Edgar Award for Best Mystery Play...
Key West
"Endless Summer" Fundraiser with Howard Livingston & friends at Tennessee Williams Theater
Apr 11, 2026
Escape to Key West for "Endless Summer"—a Trop Rock fundraiser with Howard Livingston & friends at the Tennessee Williams Theatre on April 11, 2026...
Featured
Key West
Soul Collage: Art for Everyone with Sharon DiGiulio
Apr 11, 2026, Apr 12, 2026
April 11, 12, 2026 Explore creativity and self-discovery in Soul Collage: Art for Everyone with Sharon DiGiulio at The Studios of Key West, a...
Key West
Poetry On Fire: A Spoken Word Project for Teens
Apr 11, 2026
Ignite your voice and step into the energy of performance in Poetry on Fire with Cricket Desmarais, a dynamic, expressive workshop designed to help...
Key West
Gabrielle Stravelli: Spotlight…Encore! Curated by Randy Roberts
Apr 12, 2026
Award-winning jazz vocalist Gabrielle Stravelli joins acclaimed pianist and singer Billy Stritch, along with special guest Randy Roberts, for an...
Key West
Truman Music Series: Key West Jazz Society Presents: The Heart Starters
Apr 12, 2026
Swing back to Truman’s Key West on April 12, 2026: The Heart-Starters perform a Truman‑era tribute on the Truman Little White House North Lawn. Gates...
