November 12 – 14, 2026 Waterfront Playhouse, Mallory Square, 407 Wall Street The Waterfront Playhouse launches its Spotlight Series with the Florida premiere of , a solo play written by Jason Odell Williams. It runs about 75 minutes and takes the form of a private tour of Michelangelo's David at the Galleria dell'Accademia in Florence, […]
Sunday, November 22, 2026 Key West Theater, 512 Eaton Street The Buena Vista Orchestra comes to the Key West Theater, billed by its presenter as the world's foremost Cuban music repertory ensemble. The group works with a revolving lineup drawn from the original Buena Vista Social Club performances and from the bands of Celia Cruz, […]
December 2 – 17, 2026 Waterfront Playhouse, Mallory Square, 407 Wall Street The Waterfront Playhouse's holiday show turns the theatre into a 1940s radio studio for It's a Wonderful Life: A Live Radio Play, Joe Landry's adaptation of the Frank Capra film. A small cast plays every role, performing the story live at microphones the […]
December 8, 2026 – January 2, 2027 · Shows at 7:00pm Red Barn Theatre, 319 Duval Street (rear) The Red Barn opens its holiday slot with Shooting Star, a two-hander by Steven Dietz, one of the most widely produced playwrights working in American theater. The setup is simple enough to describe in a sentence: two […]
January 7 – 9, 2027 Waterfront Playhouse, Mallory Square, 407 Wall Street The Spotlight Series continues with Blanche and Beyond, Steve Lawson's one-man play assembled from Tennessee Williams's own letters. It's the sequel to Lawson's A Distant Country Called Youth, which drew on the early correspondence; this one covers 1945 through 1957, the stretch that […]
29th Annual Key West Half Marathon & Runfest® January 13–18, 2027 · Race weekend January 15–17 Key West offers a multitude of exciting experiences, from its diverse restaurants and vibrant nightlife to the numerous museums and art galleries. The wide range of water sports options adds an extra layer of adventure, making it an unforgettable […]
Monday, January 18, 2027 Doors 6:30pm, Show 7:30pm · Tennessee Williams Theatre America's premiere doo wop group brings a brand-new show to the Tennessee Williams Theatre stage this January. The Doo Wop Project takes today's biggest hits and "doowop-ifies" them — reimagining contemporary songs as though they'd been written and recorded in 1958. Familiar melodies arrive […]
January 19 – February 20, 2027 · Tuesdays–Saturdays at 7:30pm Red Barn Theatre, 319 Duval Street (rear) The Red Barn follows its holiday show with Dracula: A Comedy of Terrors, the Gordon Greenberg and Steve Rosen send-up that became an off-Broadway hit and has been working its way through regional theaters ever since. The premise […]
Thursday, January 21, 2027 Doors 6:30pm, Show 7:30pm · Tennessee Williams Theatre One of Italy's most inventive performing arts companies makes a stop in Key West this January. NoGravity was founded in Rome in 2005 by artist Emiliano Pellisari, and it has spent two decades building a form of theater that doesn't fit neatly into […]
Mile 0 Fest Key West January 26–30, 2027 · Truman Waterfront Amphitheater and venues across the island 10th Anniversary — Red Dirt, Americana & Texas Country Named the #1 music festival of 2025 by USA Today, Mile 0 Fest turns Key West into a five-day music vacation each January. Evening shows run at the Coffee […]
2027 Key West Food and Wine Festival January 27–31, 2027 5 continents ~ 5 wines ~ 5 stories ~ 5 dishes ~ 5 chefs Welcome to Key West Food & Wine Festival 2027 A curated journey through the culinary heritage of five continents, featuring world-renowned chefs, their signature dishes, and the legendary wines that define […]
January 28 – February 6, 2027 Waterfront Playhouse, Mallory Square, 407 Wall Street The Waterfront's mainstage returns to Paul Slade Smith, whose The Angel Next Door played there previously, with Unnecessary Farce. Two cops have set up a sting in a cheap motel, hoping to catch the mayor taking a bribe. There are two adjoining […]
