45th Annual Key West Offshore World Championship November 1–8, 2026 · Truman Waterfront Park, Key West The 45th Annual XINSURANCE Key West World Championship runs Sunday, November 1 through Sunday, […]
12 events found.
Events
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 […]
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 […]
It’s a Wonderful Life: A Live Radio Play
Waterfront Playhouse 407 Wall Street, Key West, FL, United StatesDecember 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: […]
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 […]
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. […]
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 […]
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 […]
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, […]
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 […]
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 […]
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 & […]
