The Key West Songwriters Festival
With previous headliners including Kacey Musgraves, Maren Morris, Randy Houser and Florida Georgia Line, the Key West Songwriters Festival is the largest musical celebration of its kind. Over five days and nights, live music from top-name acts and local performers flows through the streets of Key West; it’s a tradition that has returned each spring for more than 30 years.
Events Calendar
Good times and good vibes are always on deck. Check out our activities and the local music scene at Ocean Key Resort and 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)
Sep10Haunted Tours
Explore the SPOOKY side of Key West with a haunted historical tour.
Date: May 14, 2026 - December 31, 2026
Time: Thursday evenings (varies by operator)
Location: Off-Site (Key West – walking or trolley tour)
Sep10Ocean Key Lime Bike Tour
Sightseeing the Key West way with a leisurely island bike tour that can be done in flip flops!
Date: May 14, 2026 - December 31, 2026
Time: Thursday's, 10:00 am – 12:00 pm
Location: Key West (guided bike tour)
Sep10Key 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
Sep11Snorkel 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)
Sep12Sunset 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)
Sep13World 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)
Oct16Fantasy Fest
Fantasy Fest turns Key West into a spectacle of masked processions, parties, contests and dances attended by tens of thousands.
Date: October 16 -25, 2026
Time: Varies by event
Location: Key West (multiple venues)
Oct17That Arena Rock Show
Kick of Fantasy Fest 2026 with iconic rock music over the water on the world-famous Sunset Pier.
Date: October 17 & 18, 2026
Time: 7:00 PM
Location: Sunset Pier
Oct19Mrs. Roper Romp, Costume Contest
Get your caftans ready and that signature curly red wig for a groovy costume party on Sunset Pier.
Date: October 19, 2026
Time: 5:00 PM
Location: Sunset Pier
