

Live at Sunset Pier – Claire Finley
Join us at the Sunset Pier for live music over the water as you enjoy tropical libations and delicious bites.
Calendar of Events
Sep03Key West Farmers Market
Visit the Key West Farmers Market every Thursday at the Truman Waterfront.
Date: May 14, 2026 - December 31, 2026
Time: Thursday's, 2:00 pm – 7:00 pm
Location: Truman Waterfront
Sep03Live at Sunset Pier - Tom Curtis
Join us at the Sunset Pier for waterfront live music, breathtaking sunset views and delicious cocktails and bites.
Date: September 1, 2026 | September 3, 2026 | September 8, 2026 | September 15, 2026
Time: 6:30 pm - 8:30 pm
Location: Sunset Pier
Sep04Be Transformed at SpaTerre
Coconut Crush Body Renewal. Exfoliating brown sugar and Tahitian Coconut Shells buff away tired skin cells to allow maximum hydration.
Date: May 15 - December 31, 2026
Time: Friday's, All day (by appointment)
Location: SpaTerre
Sep04Just a Few Friends, Favorite Son Celebration
Just a Few Friends is a one-of-a-kind festival celebrating music, community, and island life in beautiful Key West over Labor Day Weekend.
Date: September 3 - 11, 2026
Time: Varies by event
Location: Key West (multiple venues)
Sep04Snorkel Experience
Dive into the 3rd largest coral barrier reef in the world and the only barrier reef in the continental United States.
Date: May 8 - December 31, 2026
Time: Friday's, varies by tour operator
Location: Off-Site (Catamaran / Key West waters)
Sep04Live at Sunset Pier – Gi Buxdorf & Jack Wolf
Join us at the Sunset Pier for live music over the water as you enjoy tropical libations and delicious bites.
Date: September 4, 2026 | September 11, 2026 | September 18, 2026 | September 25, 2026
Time: 1:00 pm - 4:00 pm
Location: Sunset Pier
Sep04Live at Sunset Pier – Jerico Rockability Quartet
Join us at the Sunset Pier for waterfront live music, breathtaking sunset views and delicious cocktails and bites.
Date: September 4, 2026 | September 11, 2026 | September 18, 2026 | September 25, 2026
Time: 6:30 pm - 8:30 pm
Location: Sunset Pier
Sep05Sunset Sails
There is nothing quite like a Key West sunset, and the second-best place to view one (after the Sunset Pier, of course) is out on the water.
Date: May 9, 2026 - December 31, 2026
Time: Saturday's, Varies (sunset)
Location: Off-Site (Key West waters)
Sep06The Wheeland Brothers Private Poolside Concert
Join us for a Just A Few Friends, exclusive Ocean Key Resort poolside concert.
Date: September 6, 2026
Time: 12:00 pm - 1:30 pm
Location: LIQUID Pool Bar & Lounge
Sep06World Class Fishing
The Florida Keys are known for amazing fishing. From the flats and shallows, sight fishing for permit, tarpon or bonefish or in the deeper waters of the backcountry, on the hunt for snapper, grouper or tuna.
Date: May 10, 2026 - December 31, 2026
Time: Sunday's, Varies by charter
Location: Off-Site (Florida Keys waters)