

Key West Annual Holiday Parade
Each year locals gather as the holiday spirit parades down Duval Street and through the streets of Old Town. Join in the festive fun and enjoy floats creatively decorated in Key West style.
Date
December 5, 2026
Time
6:30 pm
Location
Truman Ave and Duval Street
Calendar of Events
Nov12Haunted Tours
Explore the SPOOKY side of Key West with a haunted historical tour.
Date: May 14, 2026 - March 31, 2027
Time: Thursday evenings (varies by operator)
Location: Off-Site (Key West – walking or trolley tour)
Nov12Key West Farmers Market
Visit the Key West Farmers Market every Thursday at the Truman Waterfront.
Date: May 14, 2026 - March 31, 2027
Time: Thursday's, 2:00 pm – 7:00 pm
Location: Truman Waterfront
Nov13Snorkel 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 - March 31, 2027
Time: Friday's, varies by tour operator
Location: Off-Site (Catamaran / Key West waters)
Nov14Sunset 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 - March 31, 2027
Time: Saturday's, Varies (sunset)
Location: Off-Site (Key West waters)
Nov14Key West Oyster Fest
A Benefit for the Gulf Oyster Featuring Chef Travis Lee
Date: November 14, 2026
Time: 5:00 pm - 10:00 pm
Location: Half Shell Raw Bar
Nov15World 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 - March 31, 2027
Time: Sunday's, Varies by charter
Location: Off-Site (Florida Keys waters)
Nov26Thanksgiving Dinner at Café Marquesa
Gather together in the heart of Old Town for an exquisite Thanksgiving evening.
Date: November 26, 2026
Time: By Reservation
Location: Café Marquesa
Dec04Key West BeLighted Bike Ride
Kick off the holiday season with a festive celebration at the Coffee Butler Amphitheater followed by a BeLighted bike ride
Date: December 4, 2026
Time: 5:00 pm - 9:00 pm
Location: Coffee Butler Amphitheater
Dec12Lighted Boat Parade
Gather at the Sunset Pier to watch the Annual Lighted Boat Parade.
Date: December 12, 2026
Time: 8:00 pm
Location: Sunset Pier
Dec24Christmas Eve and Christmas Day Dinner
Celebrate the joy of the holiday with a festive four-course prix fixe menu.
Date: December 24 – 25, 2026
Time: By Reservation
Location: Café Marquesa