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Key West tours

Season's Greetings

Much in the same way Harry S. Truman retreated to his Little White House when things got a little too cool for comfort up in DC, Key West is where Santa comes to spread cheer and hang out in his Christmas-themed board shorts. This is one of the best places on Earth to celebrate the holiday season, just ask Conchy The Sandman and Rudy The Bottle-nosed Dolphin!

Be part of the fun on a Holiday Lights & Sights Tour when the island goes all out with a glimmering festival of lights!

Your sleigh for the day will take you to some of the most resplendent island homes whose owners enter into a friendly competition for the most beautiful house on the block! The pre-tour festivities begin with some delicious cider and cookies then off you go for a holiday experience you can only find here!

Old Town Trolley's Holiday
Lights & Sights Tour


For a truly relaxing and festive Key West experience, head over to Mallory Square and board the Old Town Trolley. Sip cider and indulge with holiday cookies as the Holiday Trolley transports you through the city in search of the best holiday light displays. You’ll even be given special holiday lights glasses to ensure you enjoy all the sparkle. This 1-hour tour runs on select days throughout December.



Conch Tour Train Lights & Sights Tour


Ho-Ho-Ho! Say goodbye to the snow and say hello to one of Key West’s most beloved attractions on a very special holiday evening! Before boarding the famous Conch Train, relax and enjoy some holiday nom-noms like old-fashioned cider and cookies. Once the holiday cheer has been stoked, it’s time to light up the night as we cruise through Key West and marvel at the shimmering dance of color emanating from the thousands of lights adorning the light posts, businesses, and homes of the Conch Republic. You’ll also get further into the spirit of things with some neighborhood caroling and a very special pair of glasses that enhances the light show to dazzling new levels.



Christmas Tours at The Little White House


Looking to class it up for the holidays in the warmer confines of beautiful Key West, Florida? The Truman Little White House, a former naval command station that later became the Winter White House of 33rd President Harry S. Truman and his family, is rolling out the red, white and green carpet this holiday season! This is a rare opportunity to explore this home on a very VIP-style tour. Travel back to the 1940s and 50s and sip on some bubbly or a nice, comforting cup of hot chocolate as you peruse the many antique Christmas ornaments, decor and holiday cards. You’ll get a chance to hold court at Truman’s original bar and take in all the vintage regalia belonging to the museum’s private collection. If the kids are in tow, they can have fun making their very own Little White House keepsake ornament. Space is limited so reserve your space early!

Dates: December 22, 23, 27 & 28.


Key West Holiday Lights Contest


Tis the season for some friendly, holiday-inspired competition to see which Key West home can out bling all the others during the Annual Key West Holiday Lights Contest. Sponsored by Old Town Trolley Tours, Conch Tour Train, Historic Tours of America, and Key West Energy Services, this contest for bragging rights and a $500 First Place prize really brings out the creativity and love of community of area homeowners as they work their decorative skills decking their homes with all manner of light displays that turn this sunny paradise into a winter wonderland!



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