Skip to main content
CallReserve

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

  • CC AND THE SUNSETTERS performing on the Sunset Pier stage
    Nov10

    Live 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

  • Hot Tin Roof bar with tropical mural and teal barstools at Ocean Key Resort in Key West, Florida
    Nov11

    Thanksgiving Cocktails

    Savor the season with festive fall cocktails at Hot Tin Roof.

    Date: November 2026

    Time: All day

    Location: Hot Tin Roof

  • Claire Finley performing on the Sunset Pier stage
    Nov11

    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.

    Date: Wednesdays | November 11 - November 25, 2026

    Time: 1:00 pm - 4:00 pm

    Location: Sunset Pier

  • Live rockabilly music at Sunset Pier, Ocean Key Resort, Key West, Florida — Jerico band on stage
    Nov11

    Live 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

  • A woman with a mud mask on her back at the spa
    Nov12

    SpaTerre 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

  • A lantern in the ground in a dark room and a ominous shadow in the background
    Nov12

    Haunted 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)

  • Closeup Of Champagne Glasses On Table With Red Roses And Candle
    Nov12

    Romance 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

  • 3 people biking on a Key Lime Bike tour
    Nov12

    Ocean 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)

  • Marjory Lee singing and playing guitar at Sunset Pier, Ocean Key Resort in Key West, Florida
    Nov12

    Live 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

  • A mix of fruit at the Farmer's Market
    Nov12

    Key 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