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.
A Pirate Looks Back: Jimmy Buffett Tribute Show
Comedy Key West Presents A Pirate Looks Back: Jimmy Buffett Tribute Show in Key West Comedy Key West brings island music, storytelling, humor, and lunch theater together with A Pirate Looks Back: Jim...
45th Annual Hemingway Look-Alike Contest in Key West
The 45th Annual Hemingway Look-Alike Contest and Festival takes place July 21–26, 2026, celebrating the life, literary legacy and adventurous spirit of Ernest Hemingway. The main contest activities be...
37th Anniversary Hemingway 5K Sunset Run & Paddleboard Race
Hemingway 5K Sunset Run & Paddleboard Race at Southernmost Beach Café Hemingway 5K Sunset Run & Paddleboard Race 2026 — Key West’s Iconic Summer Challenge Date: Saturday, July 25 – Sunday, J...
Lobster Mini Season 2026 in Key West
Lobster Mini Season 2026 in Key West — Dive Into the Adventure Dates: July 29–30, 2026Location: Key West, Florida & the Florida Keys Every July, Lobster Mini Season in Key West transforms the is...
Key West 28th Annual Lobsterfest 2026 - Aug. 5th thru 9th
Key West Lobsterfest 2026 on Duval Street: Five Days of Spiny Lobster, Live Music & Island Celebration Key West Lobsterfest 2026 returns for its 28th annual celebration from August 5–9, 2026, mar...
Key West Rum Fest 2026
Key West Rum Fest 2026 Key West Rum Fest 2026 returns with a packed schedule of music, art, cocktails, and signature experiences, highlighted by the announcement of Reál Infused Exotics as the Offic...
Jesse Rice at Key West Theater During Rum Fest Key West 2026
Jesse Rice Brings The Pirate Sessions to Key West Theater During Rum Fest Key West Rum Fest Key West presents songwriter and touring artist Jesse Rice live at the Key West Theater on Saturday, August...
3rd Annual Just a Few Friends Festival in Key West
3rd Annual Just a Few Friends Festival Celebrates Jimmy Buffett’s Key West Legacy The 3rd Annual Just a Few Friends Festival returns to Key West from Wednesday, September 2, through Monday, September...
Gov't Mule & Ziggy Marley in Key West
Gov’t Mule & Ziggy Marley bring the Dreaming the Same Dream Tour to Coffee Butler Amphitheater in Key West on September 30, 2026. This co-headlining night pairs Gov’t Mule’s powerful American rock...
Key West Guided Snorkel & Morning Sail
Honest Eco
Start the day on the water with Honest Eco’s Key West guided snorkel and morning sail. This trip combines a relaxed morning sailing experience with guided snorkeling, making it a strong choice for visitors who want clear water, reef time, and a more active boating adventure before the afternoon.
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Key West Discover Scuba 1-Day Resort Course
Southpoint Divers
Try scuba diving in Key West with Southpoint Divers on a Discover Scuba 1-day resort course. This introductory scuba experience is designed for visitors who want to learn basic dive skills, gain confidence with professional instruction, and experience the underwater side of the Florida Keys.
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Key West Center Console Boat Rental
Ibis Bay Water Sport
Rent a center console boat from Ibis Bay Water Sport and enjoy the freedom to explore Key West from the water. This rental is a good fit for visitors who want a flexible boating day with access to local waters, scenic cruising, and time on their own schedule.
Book now!