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The Festive Season in Key West
Thanksgiving, Christmas & New Year’s Eve, Island Style
Some traditions are worth taking somewhere warmer. In Key West, the holidays arrive with twinkling lights along historic streets, decorated boats in the harbor, and celebrations as colorful as the island itself. From Thanksgiving gatherings to Christmas festivities and a New Year’s Eve unlike any other, discover a season worth celebrating at Key West Historic Inns.
Thanksgiving Week
Good company, island sunshine, and plenty to be thankful for.
Celebrate Thanksgiving in Key West with waterfront dining, the Southernmost Turkey Trot, and the first sparkle of holiday lights along the Historic Seaport. From sunset sails to festive markets, it’s a long weekend filled with island traditions and reasons to stay a little longer.
The Key West Christmas Getaway
November 27 – January 2
Celebrate the season with a holiday escape filled with thoughtful touches, locally crafted keepsakes, and a few festive indulgences. Our Key West Christmas Getaway brings together the spirit of the island and the joy of giving, with a curated collection of gifts to enjoy during your stay and take home as a little piece of Key West.
Your Holiday Getaway Includes:
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A Little Local Artistry: A hand-poured candle from Key West’s Belle Laine, featuring an individually hand-painted label that makes each one a unique work of art.
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Something Sweet: Ferrero chocolates for a little holiday indulgence.
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A Keepsake for the Tree: A limited-edition Key West Historic Inns holiday ornament to remember your island Christmas.
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A Festive Toast: A signature Key West Historic Inns tumbler, artisan eggnog mix, and a nip of local Key West rum.
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Your Holiday, Your Way: Personalized holiday planning with our concierge to discover the island’s festive favorites.
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One More Morning: Late checkout to make the most of your getaway.
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The Gift of Giving: A donation to Give Kids The World, sharing a little holiday joy beyond the island.
A Little Extra Holiday Indulgence
Available November 27 – January 2
Make your holiday stay a little more delicious with a curated charcuterie board awaiting you in your room, paired with your choice of rosé, white, or red wine and locally harvested Key West honey. So local, in fact, the honey is named for the very street where it’s made. A keepsake olive spreader is yours to take home, too.
Ask our concierge about adding this festive experience to your stay.
Key West, All Lit Up
Christmas in Key West shines a little differently. Climb aboard a festive trolley for a holiday lights tour through historic Old Town, stroll the illuminated Harbor Walk, or watch decorated boats light up the waterfront. From twinkling streets to beloved island celebrations, there’s plenty to make the season merry.
Island Traditions
The celebrations don’t stop at Christmas lights. December brings a wonderful mix of island traditions, outdoor adventures, local shopping, and celebrations worth planning a trip around.
New Year's Eve
December 31, 2026
Forget the ball drop. Key West has a few ideas of its own.
From a glittering red high heel on Duval Street to a giant conch shell and a pirate wench descending from a schooner’s mast, New Year’s Eve in Key West is anything but ordinary. Celebrate with champagne, waterfront festivities, and some of the most wonderfully eccentric midnight traditions you’ll find anywhere.