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 & Festive Nights Tour! The Southernmost City is all a twinkle, as the locals decorate their historic Key West homes in a splendid cascade of lights and other decorative touches to see who can outdo the other in a friendly, holiday-inspired competition – see all the best decorations on our holiday tour.
Take in awesome sights and excellent narration highlighting fun facts about the island. Give you and yours the gift of Key West this year!
Just a quick look-see at all the cool stuff you’ll be enjoying on your holiday tour!
2023: December 8-23.
6:30pm, 7:00pm, 8:00pm and 8:30pm.
Limited capacity: 35 seats per trolley.
VIP passes cannot be accepted or used for Holiday Tours. Reservation-based tickets are non-refundable. You may reschedule up to 24 hours in advance of tour time. Guests should check in at the booth 15 minutes prior to their scheduled tour.
Large group bookings are not guaranteed to sit together.
This contest for bragging rights and a $500 First Place prize really brings out the creativity and love of the 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!
Lighting of the 2023 Harbor Walk of Lights
Harbor Walk Plaza at Greene and Elizabeth St.
Holiday Artisan Market
Studios of Key West, 533 Eaton Street
Pet Pictures with Santa
Key West Harbor Walk
6 pm – 8 pm
Key West Holiday Parade
Parade begins on Truman at White and heads to Duval Street ending at Eaton Street.
Key West Art & Historical Society Annual Holiday Concert and Bazaar
281 Front Street
5 – 9 pm
Schooner Wharf Annual Lighted Boat Parade
Key West Harbor Walk
Christmas at the Sheriff’s Animal Farm
5525 College Road
1 pm – 3 pm
Key West Waterfront Winter Wonderland
Coffee Butler Amphitheater at the Truman Waterfront Park