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 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.

December 5-8, 13-15, 2024
Nutcracker Key West
Tennessee Williams Theater, 5901 College Rd.
Performed every other year, Nutcracker Key West is a sumptuous, artful theatrical experience wrapped as a perfect holiday gift for the Southernmost City, returning December 2024. The Key West production comes complete with chickens, roosters, sea fans, anemones, and yes, even a conch shell. Showtimes vary.

December 5, 2024
Truman Waterfront Farmers Market
2:00 pm – 7:00 pm
Truman Waterfront Park
Weekly market featuring fresh fruit and produce, eat-in or take-away food vendors, arts, crafts and other merchandise. Rain or shine.

December 5, 2024
Pet Pictures with Santa
6:00 pm – 8:00 pm
Key West Bight Marina/Harbor Walk of Lights
Bring Fido, Fifi and the family for Pet Pictures with Santa, hosted by All Animal Clinic. Photos are taken from 6-8 p.m. at the nautical Christmas tree at the foot of William Street. A $25 cash-only donation provides a professional high-resolution digital image, with proceeds benefiting the Boys & Girls Club of the Keys.

December 5-6, 2024
Key West International Dance Co.: Fiesta de Navidad Tropical
8:00 pm – 10:00 pm
San Carlos Institute
Fiesta de Navidad delivers a festive extravaganza to ignite the holiday spirit. With world-class Latin dance and vibrant costumes, this joyful celebration also offers the opportunity for audience members of all ages to dance on stage with a live band! Get ready for a holiday extravaganza like no other! Fiesta de Navidad is here to light up your season with beloved holiday characters and incredible Latin dance from salsa to cha-cha-cha. Highlighting the rich cultural influences that make Key West so unique, this show is a high-energy spectacle that will have everyone from kids to grandparents dancing.

December 6, 2024
Holiday Village & BeLighted Bike Ride
5:00 pm – 9:00 pm
The Wesley House Family Services Holiday Village is the family-friendly pre-party for the BeLighted Bike Ride, creating an evening of joy, laughter, and holiday magic for all ages. The Holiday Village will feature over 20 community booths offering games and activities, carnival rides, bounce houses, local food trucks, community performances, snowfalls and Santa! The highlight of the evening is the BeLighted Bike Ride that departs from the event held at Coffee Butler Amphitheater. Admission is $20 per person or four tickets for $70. Children aged 3 and under enter free.

December 7, 2024
City of Key West’s Annual Holiday Parade
6:30 pm – 9:30 pm
Charming holiday spirit abounds in this annual parade in the southernmost city in the continental U.S. Local flavor prevails with marching bands, school groups, motorized and non-motorized floats and lively community participation. The parade kicks off at Truman Avenue and White Street beside Bayview Park and proceeds down Duval Street. Seeing Santa is a highlight for kids.

December 8, 2024
Key West Artisan Market at Southernmost Beach Resort
10:00 am – 3:00 pm
Join the Key West Artisan Market and the Southernmost Beach Resort for a very special holiday event on the beach. Find some of your favorite local artists with the perfect gifts for everyone on your list along with lots of activities for the kids, great food, tasty treats, fun drinks and even a visit from old St. Nick himself! Live music all day and a fun sand ‘snowman’ building contest.

December 8, 2024
Christmas on the Sheriff’s Animal Farm
1:00 pm – 3:00 pm
Stock Island
Children and adults are invited to visit the unique Monroe County Sheriff’s Office Animal Farm for a special holiday open house. It’s located just northeast of Key West at 5501 College Road. Holiday donations are encouraged. Call 305-293-7300 for more information.

December 8, 2024
Eaton Street Christmas Stroll
3:30 pm – 7:00 pm
Eaton Street becomes a southernmost North Pole. Wander the blocks between Whitehead and Simonton, stopping at venues like Williams Hall for a concert from the Bahama Village Music Program, Tropic Cinema for some classic cartoons, The Studios for cocktails, and ending at St. Paul’s for a traditional Christmas concert. The Studios of Key West hosts an open house for the duration of the evening. Visitors can check out the members’ winter exhibition or plan to come by for festive cocktails on the roof at sunset.

December 13-23, 26-28, 2024
Waterfront Winter Wonderland
21 Quay Rd.
Make your Key West holiday experience even more magical at Waterfront Winter Wonderland at Truman Waterfront Park. Coffee Butler Amphitheater transforms into an amazing winter wonderland, with ice skating, rides, games, music, holiday lights, a vendor village with food and local artisans, and more (closed Christmas Eve and Christmas). General admission is $10, free for children ages 5 and under. Additional fees apply for ice skating and rides.

December 13, 2024
Key West Art & Historical Society: Holiday Concert & Bazaar
5:00 pm – 9:30 pm
281 Front St.
Join the Key West Art & Historical Society for the 7th Annual Holiday Concert & Bazaar. The event is located on the sweeping historic porch and street in front of the Custom House Museum. The immensely popular celebration will feature some of Key West’s finest artisans, musicians and choirs, food and libations, and a holiday light show designed by Key West High School’s Conch 5 Studios, which will be projected on the face of the Custom House. There will be plenty of food and festive libations at this event along with excellent holiday shopping. The event is free and open to the public.

December 13, 2024
Holiday Lighted Boat Parade of Stock Island
5:30 pm – 9:00 pm
The Perry Hotel & Marina
The Rotary Club of Key West and the Perry Hotel & Marina present the Holiday Lighted Boat Parade of Stock Island, on the lawn of the Perry Hotel on Stock Island. This event will be family-friendly with games, activities and treats for the children. Santa, Mrs. Claus, Rudolph and the elves will come all the way from the North Pole. There will also be a surprise appearance by the Grinch. Photo opportunities will be available.

December 14, 2024
Schooner Wharf Bar Lighted Boat Parade
8:00 pm – 9:00 pm
Don’t miss this magical nautical display of holiday lights on board every manner of watercraft in Key West Harbor. The judges’ stand is located at Schooner Wharf, 202 William St. Viewing is available from all along the Harbor Walk. The parade starts at 8 p.m.

December 15, 2024
Snowy Days Children’s Concert at Key West Botanical Garden
1:00 pm – 3:00 pm
Snowy Days, the Key West Tropical Forest & Botanical Garden’s annual children’s winter concert, features Key West vocalist, Belle Jampol performing favorite holiday tunes for children. The event opens at 1 p.m. and the concert starts at 1:30 p.m., followed by snow cones (while they last) and delightful holiday arts and crafts, face painting and special treats. Tickets are $5 per child at the door with a maximum cost of $10 per family.

December 29, 2024
Key West Lighting of the Menorah
5:00 pm – 7:00 pm
The City of Key West’s annual Lighting of the Menorah ceremony takes place at Bayview Park