Calendar of Events
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
Sep05Just 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)
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)
Sep06Sunday Brunch
Come experience one of the Island’s best waterfront brunches featuring unlimited traditional Florida and Caribbean inspired shareable plates.
Date: May 17, 2026 - December 31, 2026
Time: 11:45 am – 12:45 pm
Location: Hot Tin Roof
Sep06Live at Sunset Pier - Mike Stack & DLew
Join us at the Sunset Pier for live music over the water as you enjoy tropical libations and delicious bites.
Date: Sunday | September 6, 2026
Time: 1:30 pm - 4:30 pm & 6:30 pm - 8:30 pm
Location: Sunset Pier
Sep08Double Dip Snorkel Trip
Explore the turquoise waters of the 3rd largest coral barrier reef, teeming with fish, coral, sea turtles and more.
Date: May 12, 2026 - December 31, 2026
Time: Tuesday's, 2:00 pm – 5:00 pm
Location: Off-Site (Catamaran / Key West reef)
Sep08Live 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
Sep09Live 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 2, 2026 | September 9, 2026 | September 16, 2026 | September 23, 2026 | September 30, 2026
Time: 6:30 pm - 8:30 pm
Location: Sunset Pier
