Discover the best festivals and events in Key West!
From captivating theater performances and comedy shows to exhilarating fishing tournaments and literary seminars, our curated event listings offer unforgettable experiences year-round. Plan your perfect Key West getaway and immerse yourself in the vibrant local culture, entertainment, and island charm.
Southernmost Regatta 2026
Southernmost Regatta 2026 — Key West Sailing Competition & Island Culture The Southernmost Regatta 2026 returns to Key West, Florida from January 19–23, 2026, bringing together elite sailors and ...
White Party | Comedy Key West
White Party Wine Tasting at Comedy Key West Comedy Key West hosts the White Party Key West on Monday, January 19, 2026, offering an early-evening social experience centered around white wine, light b...
34th Annual Kelly McGillis Classic International Female Flag Football Championship
Kelly McGillis Classic Flag Football Championship | Key West, Florida Kelly McGillis Classic Flag Football Championship in Key West, Florida The Kelly McGillis Classic International Women’s & Gi...
Trivia Night at Celtic Conch | Free Key West Trivia Night
Trivia Night at Celtic Conch Trivia Night at Celtic Conch delivers a spirited midweek social event that blends friendly competition with classic Key West pub energy. Held in a relaxed, welcoming sett...
Susan Werner at The Studios of Key West
Susan Werner Live at The Studios of Key West – Old Town New Folk Concert Series Susan Werner brings her acclaimed songwriting and virtuoso musicianship to The Studios of Key West as part of the Old T...
Ben Harrison at Key West Theater – Backstage Listening Room
Ben Harrison at Key West Theater – Backstage Listening Room Performance Wednesday, January 21, 2026 at 7:00 PM, Harrison Gallery Presents an intimate live performance by Ben Harrison in the Backstage...
Rumours ATL- A Fleetwood Mac Tribute
Key West Theater Presents Rumours ATL - A Fleetwood Mac Tribute On January 21, 2026, music enthusiasts will gather at the Key West Theater for an unforgettable evening with Rumours ATL: A Fleetwood M...
Jordan Rock Live | Comedy Key West
Jordan Rock Live at Comedy Key West Comedy Key West welcomes acclaimed stand-up comedian Jordan Rock for four nights of sharp, intelligent comedy in the heart of Old Town. Performances take place Wed...
The Young Dubliners Hot Toddy Tour | Key West Theater
The Young Dubliners Hot Toddy Tour at Key West Theater The Young Dubliners: The HOT TODDY Tour brings high-energy Celtic Rock to Key West Theater on Friday, January 23, 2026, delivering a powerful li...
