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Holiday Magic in Paradise: Your 2025 Guide to Key West’s Festive Events

  • Writer: Krystal Thomas
    Krystal Thomas
  • Nov 19
  • 2 min read

Because palm trees look even better wrapped in twinkle lights. 


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The holidays hit different down here in Key West instead of snowflakes, we get salt air; instead of fireplaces, we gather by the water. But trust us, the island knows exactly how to bring the festive spirit, island-style!


Lighted Boat Parade – December 14, 2025

Nothing says “Florida Christmas” quite like a parade of boats decked out in twinkling lights, wreaths, and inflatable flamingos. The Key West Lighted Boat Parade is a local legend picture yachts, fishing boats, and even kayaks gliding through the Historic Seaport, all aglow.

Pro tip: Grab a spot early along the Harbor Walk or book a dinner reservation at one of the waterfront restaurants for the best view (and a margarita in hand).


Holiday Historic Inn Tour – December 6 & 13, 2025

Take a stroll through Key West’s most charming inns, each dressed up for the holidays with island flair. Think lush tropical wreaths, vintage decorations, and plenty of warm welcomes.

This annual event supports the Hospice & Visiting Nurse Association, so you’ll be giving back while soaking in some serious holiday charm.

Don’t miss: Complimentary treats and cocktails at each stop a little taste of local hospitality never hurts!


Key West Holiday Village – All December at Truman Waterfront Park

The Key West Holiday Village turns Truman Waterfront Park into a twinkling wonderland the whole month of December. Expect festive lights, a pop-up market, food trucks, live music, and even a visit from Santa (who, yes, sometimes arrives by boat).

It’s perfect for families, date nights, or anyone who just wants to stroll through holiday cheer in board shorts.


Bonus Festivities You’ll Love

  • Historic Seaport “Bight Before Christmas” Celebration – nightly lights, carolers, and waterfront vibes.

  • New Year’s Eve Drops – from the famous Conch Shell at Sloppy Joe’s to the Red Shoe Drop on Duval, Key West rings in the New Year like no one else.

  • Island Holiday Markets – shop local for handmade gifts, art, and tropical ornaments you won’t find anywhere else.


Tag your photos with #KeyWestHolidays and share the island magic because down here, Christmas is all about sunshine, smiles, and a touch of salt air.

 
 
 

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