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  • Chelsea Susan Bednar

Spend the Holiday Season in Key West!

Tis’ the season for all things dazzling and festive! Key West is filled with merry activities for everyone to enjoy. While it may be sunny and hot, holiday festivities are hotter! From the classic ‘Lighted Boat Parade’ to the popular burlesque performance of ’12 Days of Stripmas’, there will be something to add to your activity wishlist. Below we’ve curated a list of both naughty & nice events to partake in this holiday season while staying in Key West.



Holiday Concert & Bazaar


Cost: FREE

Location: Custom House 281 Front Street Naval Air Station Key West, FL 33040

Hours: 4:00 PM – 6:00 PM EST

Dates: December 9, 2022


Join the Key West Art & Historical Society at the Custom House Museum on December 9, 2022 for the 6th Annual Holiday Concert & Bazaar. This popular celebration takes place on the wrap-around historic porch & walkway of the house, featuring live musicians, choir singers, and a holiday light show! Lots of food and drinks will be served throughout the evening. This event if FREE and open to the public. Vendors at the Bazaar include local artisans and makers who will be selling handcrafted clothing, jewelry, home decor, handmade soaps and scrubs, along with various home baked goods.

Key West Lighted Boat Parade


Cost: $89.96 Adults | $49.95 Children 4-11 | Free for children 3 & under

Location: 205 Elizabeth Street. Key West, FL 33040

Hours: 7:30 PM - 9:30pm (duration: 2 hours)

Dates: Saturday, December 10th

Join Sebago Watersports as they host their 31at Annual Key West Lighted Boat Parade on December 10, 2022! The family fun festivities are a spectacle for all to see as boats of all shaped and sizes are decked out for the holidays. All boats are entered in a contest for “Best Nautical Holiday Decorations in Key West” to add to the holiday spirit.

Fury Lighted Boat Parade


Cost: $89.95

Location: Departure Point 3 HISTORIC SEAPORT Located on the corner of Greene St. and Elizabeth St.next to The Conch Republic Seafood Company.

Hours: 7:30 pm - 9:30 pm

Dates: December 10, 2022


Ride in the 31st Annual Key West Lighted Boat Parade with a friendly competitor of Sebago, Fury! Enjoy the views up close by reserving your seat on the boat beforehand. Live music, fresh appetizers, and an open bar will be included in the price of your ticket. (Our Marrero's team is riding along with Fury as they parade through the Key West Bight!)

The 12 Days of Stripmas (21+ Event)

Cost: tickets starting at $76.00

Location: Key West Theater, 512 Eaton Street, Key West, Florida

Hours: 8:00pm | Doors open 7pm

Dates: Friday December 16th & Saturday 17th, 2022


In the true nature of Key West culture, get into a flirtatious holiday spirit and attend the burlesque performance, “The 12 Days of Stripmas” at the Key West Theatre. This event combines tongue-in-cheek comedy and incredible burlesque talent to present a performance you’ll never forget! Featured in the show are local performers along with a few special guests. Email any questions to boxoffice@thekeywesttheater.com.

Old Town Trolley Holiday Lights and Sights Tours


Cost: Adults $29 | Children $19 (3-12) | Children under 3 are free

*5% city fee added to all tickets

Location: Mallory Square Key West, FL 33040 United States

Hours: Times vary from 8am to 5pm - check website for specifics

Dates: All through December (start Dec 8. end Dec. 23)

Ride the iconic Old Town Trolley on their specialty ‘Holiday Lights and Sights Tour,' running all throughout the month of December. Passengers will be enamored with the decorated streets and historic neighborhoods, lit up by dazzling lights and colorful holiday decor.

Conch Tour Train Holiday Sights and Festive Nights Tours


Cost: Adults $30.95 Children $19.95

Location: Key West High School 2100 Flagler Ave Key West, FL 33040

Hours: 6:30pm-8:30pm

Dates: Dec 8, 11-13, 16-23


Partake in Key West’s classic Conch Tour - Holiday Sights Train that’s decked out for the holidays! These nightly tours are scheduled all throughout December, taking off from Key West High School and traveling throughout the sparklingly decorated neighborhoods. It’s a grand time not to be missed!




We hope this list has provided you with inspiration for your seasonal travels, and we wish you all things merry and bright.

Happy Holidays! Thanks for reading, The Marrero’s Team


Traveling elsewhere in Florida? Visit our sister property in Treasure Island FL.



Remember to follow Marrero's on Instagram and Facebook, and tell us about your stay over at Trip Advisor. We look forward to hosting your next beach getaway!

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