

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
Nov10Live at Sunset Pier – CC & The Sunsetters
Join us at the Sunset Pier for waterfront live music, breathtaking sunset views and delicious cocktails and bites.
Date: Tuesdays | November 3, 2026 - November 24, 2026
Time: 5:00 pm - 7:00 pm
Location: Sunset Pier
Nov11Thanksgiving Cocktails
Savor the season with festive fall cocktails at Hot Tin Roof.
Date: November 2026
Time: All day
Location: Hot Tin Roof
Nov11Live 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.
Date: Wednesdays | November 11 - November 25, 2026
Time: 1:00 pm - 4:00 pm
Location: Sunset Pier
Nov11Live 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: Wednesday & Fridays | November 4 - November 25, 2026 & November 6 - November 27, 2026
Time: 5:00 pm - 7:00 pm
Location: Sunset Pier
Nov12SpaTerre VOYA Treatments
Relax and rejuvenate the natural way! VOYA Organic Seaweed Treatments.
Date: May 14, 2026 - March 31, 2027
Time: Thursday's, All day (by appointment)
Location: SpaTerre
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)
Nov12Romance at Hot Tin Roof
Add some romance to your dining experience with a chilled bottle of Lallier Reserve Brut champagne and your table decorated with rose petals
Date: May 14, 2026 - March 31, 2027
Time: Thursday's, During Hot Tin Roof dining hours
Location: Hot Tin Roof
Nov12Ocean 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 - March 31, 2027
Time: Thursday's, 10:00 am – 12:00 pm
Location: Key West (guided bike tour)
Nov12Live at Sunset Pier – Marjory
Join us at the Sunset Pier for live music over the water as you enjoy tropical libations and delicious bites.
Date: Thursdays | November 5, 2026 - November 19, 2026
Time: 1:00 pm - 4:00 pm
Location: Sunset Pier
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