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...
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 Key West 2026
The 3rd Annual Just a Few Friends Festival returns to Key West for Labor Day Weekend 2026, with official festival events September 3–7 and early kickoff activities beginning Wednesday, September 2. Th...
Key West Labor Day Weekend 2026
Key West celebrates Labor Day Weekend September 3–7, 2026, with five days of concerts, street parties, food events, races, waterfront activities and celebrations across the island. The holiday weekend...
Cheeseburger Beach Battle & Tribute Concert 2026
The Cheeseburger Beach Battle & Tribute Concert brings a toes-in-the-sand food competition and live music to Southernmost Beach Resort on Thursday, September 3, 2026, from 5:00 PM to 8:00 PM, help...
Duval Street Party featuring Gary & the Landsharks
Friday night brings one of the biggest free celebrations of the Just a Few Friends weekend directly to Duval Street. From 5:30 PM to 9:00 PM, the 200 block of Duval Street becomes an open-air concert ...
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 oktoBREWfest 2026
Key West oktoBREWfest 2026 Key West oktoBREWfest returns on Saturday, October 3, 2026, bringing one of the island’s biggest beer celebrations to Southernmost Beach Resort at 1319 Duval Street. The m...
Key West Single-Day Bicycle Rental
Pirate Scooter Rentals
Explore Key West for the day with a bicycle rental from Pirate Scooter Rentals. A single-day bike rental is a simple, affordable way to cruise Old Town, visit beaches, stop at local attractions, and enjoy the island without worrying about parking.
Book now!
Key West Mini Cooper Convertible Rental
Key West Adventures
Cruise Key West in a Mini Cooper convertible rental from Key West Adventures. This stylish open-air rental is a fun way to explore the island, enjoy scenic streets, visit beaches, and make getting around town part of the experience.
Book now!
Private Fishing Charter
Eva Marie - Key West Fishing Charters
Experience a Key West fishing charter aboard a 43-foot boat with cool A/C and top tackle.
Book now!