How to Have a Perfect Holiday Vacation in Key West

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The southernmost city in the U.S. is filled with holiday lights, trimmed-trees, and cheer in December.

Considering the fact that Key West still has weather in the high 70s in December, they sure do know how to get into the holiday spirit. From decorating their charming bed and breakfasts, to parading Christmas light-lined sail boats through the Key West Bight, there is no shortage of Floridian ways to celebrate the season. Whether you’re stopping in Key West for 24 hours after a Miami business trip, or your whole family is heading to the Keys for the holidays this year, these activities will make for a perfect holiday vacation in Key West:

Take a holiday tour of the Little White House


Courtesy Historic Tour's of America

President Harry S. Truman had his very own little white house on Key West, and the halls of his elegant former abode are fully decked during the holiday season for all to see. Visitors to Little White House can order champagne or hot chocolate at the 33rd President’s very own bar. Those on the holiday tour can then see the museum’s private collection while reveling in the holiday décor.

Check out the Lighted Boat Parade

An annual Floridian holiday tradition, the Key West Lighted Boat Parade sees local boats get dolled up in Christmas décor, with lights on their masts and tinsel on their sails. The parade winds through Key West Bight all the way to the judges’ stand at Schooner Wharf Bar & Galley. Watch from docks lining the Key West Bight, or watch from the water aboard a luxe catamaran with appetizers and drinks through Fury Water Adventures.

See the charming inns of Key West all dressed up for the holidays


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The bed and breakfast game is strong in the southernmost part of the U.S. And the historic inns spare no decorative expense in December. The Avalon Bed & Breakfast goes all out with Christmas lights, so that’s a good place to start. You’ll also want to see the lush décor at Old Town Manor and The Mermaid & The Alligator. Pro tip: you don’t have to do a self-guided tour to see the inns of Key West. You can instead join the Florida Keys Holiday Historic Inn Tour, which happens each December.

Stroll the Harbor Walk of Lights

If you’re in Key West in November, the community often gathers for the lighting of the Harbor Walk of Lights, which typically happens around Thanksgiving. Even if you don’t make it for the inaugural lighting, you’ll still want to stroll the Harbor Walk of Lights during the holiday season to see three trees that steal the show: the Nautical Christmas Tree, the Fishing Buoy Christmas Tree, and Lobster Trap Christmas Tree.

Take the Old Town Trolley’s Holiday Lights & Sights Tour


Courtesy Historic Tours of America

A walking tour and a trolley tour? Get you a city who can do both. The Old Town Trolley leaves from Mallory Square, and each holiday season, the trolley takes passengers in pursuit of the best light spectacles in the city. Passengers onboard the trolley are treated to holiday cookies and hot cider. The Old Town Trolley also run a lights and sights tour on their famed open-air Conch Train.

Reserve a dinner table at Little Pearl

If you grew up eating seven courses of fish and seafood on Christmas Eve and still long for a fresh-caught meal around the holidays, dining at Little Pearl in Key West is a must. In Old Town, Little Pearl serves some of the freshest seafood and fish, and it’s the perfect spot to celebrate the holidays or any special occasion. Don’t skip their caviar service and other sumptuous raw bar offerings.

Finish your holiday shopping at the Duval Street boutiques


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Start at Tucker’s Provisions, which has a laid back vintage aesthetic perfect for Key West vacationers. You’ll also want to spend plenty of time at The Green Pineapple, one of the trendiest shops in Key West right now. With notes of California wellness culture, the shop also has a yoga studio, a spa, and an organic café. Finally, wind your way to Country Conch and Key West Shells & Gifts for gifts with a true southern Florida, oceanic feel.

Where to stay


Courtesy Waldorf Astoria Hotels & Resorts

Casa Marina Key West, a Waldorf Astoria Resort is situated on 1,100 feet of beach available only to hotel guests. For a family vacation during the holiday season, guests can rent an oceanfront, two-bedroom loft suite with a balcony. Casa Marina Key West’s Spa Al Mare hosts yoga classes on Casa Marina’s East Beach and offers in-room treatments.