Ho ho ho! Bring the family for a festive Key West holiday moment with Santa himself at The Shops at Mallory Square. Enjoy photos, holiday cheer, and a little island Christmas magic — perfect for families, friends, and visitors of all ages! Join us at the Shops of Mallory Square for a festive afternoon filled...
Parade starts on Truman Ave. (at White St.) then proceeds to Duval St., then down Duval St. ending at Eaton St. The most charming hometown parade you’ll ever see with holiday floats, and tons of kids (of all ages). Of course Santa will make a guest appearance! Parade goes south down Truman Avenue to Duval...
Our Hugh’s View roof terrace offers the best views in town, and an ideal spot to catch the sunset and a drink with friends. The bar is open, admission is free, and everyone looks great in the golden twilight. Free and open to the public on Monday's and Tuesdays from 6pm-8pm
Test Your Knowledge & Tastebuds every Monday from 6:00 to 8:30 PM for a sizzling evening of fun, food, and friendly competition at Trivia Night at the Key West Cooking School! Gather your team or come solo and make new friends as we challenge your brain with a mix of pop culture, history, food facts,...
No need to gas-up the snowblower this year if you’re planning a holiday escape to the Conch Republic! Here, ‘Christmas chill’ means rockin’ your flops and kicking back island-style and one of the best ways to do that is hopping a ride on Old Town Trolley’s Holiday Sights and Festive Nights Tour! The Southernmost City...
Our Hugh’s View roof terrace offers the best views in town, and an ideal spot to catch the sunset and a drink with friends. The bar is open, admission is free, and everyone looks great in the golden twilight. Free and open to the public on Monday's and Tuesdays from 6pm-8pm
Join us every Thursday from 2 pm to 7 pm at the Truman Waterfront for fresh produce grown in Homestead, gorgeous orchids & native plants, artisan selection of meats and cheeses, pickles, honey, nuts & dried fruits, natural soaps and so much more. You’ll find Key West crafts, gifts and the perfect souvenir to take...
Join us for an enchanted evening of decorated historic inns while enjoying light sweet or savory holiday treats and holiday cheer at each property. Visit each property, explore the unique architecture and history, and delight in holiday ambiance in a tropical setting. The tours are self-guided. Free trolley transportation will be provided between properties -...
Come one, come all to the Great Gingerbread Build at the Harry S. Truman Little White House. This event is free and open to the public. We will have gingerbread crackers, icing, and all sorts of candies to decorate your house with or we will also have a limited amount of kits available to buy...
Movies Under the Stars Kick off the holiday season with a magical night under the stars! In Tim Burtons beloved stop-motion classic The Nightmare Before Christmas, Jack Skellingtonthe Pumpkin King of Halloween Townstumbles upon Christmas Town and decides to bring the holiday spirit home with some spooky twists. This family-friendly favorite is full of music,...
