Over the past 20+ years, we’ve created hundreds of Holiday Season Vacations in Key West. We love sharing this special time of year with our guests. On this page, we highlight some of Key West’s best 2024 Christmas and holiday events.

Wed, Nov 27 through New Year’s Eve

Lighting up the Waterfront!!

Lighting of the “Harbor Walk of Lights”
Lights come on at 5 pm

Nov. 27: Lighting of the Harbor Walk of Lights. Key West. The Harbor Walk of Lights at the Key West Historic Seaport stretches along the harbor past Greene, William and Margaret streets to the Key West Ferry Terminal. Activities include lighting of a 20-foot-tall Fishing Buoy tree and a Key West Lobster Trap tree. Music begins at 5 p.m. beside the Fishing Buoy tree, with the lighting at 6 p.m. Music at the Lobster Trap tree is to begin at 6 p.m., with its lighting at 7 p.m. The displays will be illuminated nightly through Dec. 31. Visit keywestchristmas.org. 

The night before Thanksgiving, Key West’s Harbor Walk of Lights switches on, illuminating the city’s Historic Seaport area. The area stays illuminated nightly through New Year’s Eve. Photo: Carol Tedesco.

Nov. 29-30, Dec. 5-6: Key West International Dance Co.: Fiesta de Navidad Tropical.

Key West. Celebrate the season with Fiesta de Navidad Tropical, a lively holiday show featuring world-class Latin dance, vibrant costumes and festive energy. Audience members of all ages are invited to join the performers on stage and dance to live music. Performances begin at 8 p.m. at the San Carlos Institute, 516 Duval St. for tickets and information, visit kwinternationaldancecompany.com/fiesta-de-navidad.

Key West International Dance Company’s lively holiday show features world-class Latin dance, vibrant costumes and festive energy.

Nov. 29: Black Friday Shopping Extravaganza.

 Key West. Join the Key West Artisan Market, Truman Waterfront Farmers Market and Shop Mom and Pop Key West vendors for a day of unique gifts and handmade items. Featuring local artists, crafters and makers, this event offers one-of-a-kind art, culinary delights and beverages at Truman Waterfront, 21 Quay Road. From 10 a.m. to 6 p.m., shoppers can enjoy a waterfront setting with views unlike any indoor mall. Visit facebook.com/events/1074747156827154.

Nov. 30: Lower Keys’ Island Art Festival.

Big Pine Key. Get holiday shopping off to a great start at the Lower Keys Chamber of Commerce’s Island Art Festival. Find one-of-a-kind handcrafted items that typically include jewelry, stained glass, paintings, fragrant soaps, gourmet foodstuffs and more created by talented regional artisans. Enjoy live music and food throughout the event, slated for 9 a.m. to 3 p.m. on the Chamber of Commerce grounds, mile marker 31 oceanside. Visit lowerkeyschamber.com/chamber-events/.

Art by Keys artists, holiday crafts, unique gifts and more welcome shoppers at the Lower Keys Island Art Festival on Big Pine Key.

Dec. 1, 15, 22 and 29: Artisan Market. 

Key West. A Key West holiday shopping tradition filled with one-of-a-kind gifts, the open-air bazaar is set for selected Sundays from 10 a.m. to 2 p.m. at 1801 White St. Markets feature Keys artists, authors, chef-made cuisine, craftspeople, performers, live music and adult beverages. Admission is free. Visit facebook.com/KeyWestArtisanMarket or call 305-509-3385.

Dec. 5: Pet Pictures with Santa. 

Key West. 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 along the Key West Bight Marina/Harbor Walk of Lights. A $25 cash-only donation provides a professional high-resolution digital image, with proceeds benefiting the Boys & Girls Club of the Keys. Visit keywestchristmas.org.

Pet pictures with Santa are available Dec. 5 for a $25 cash donation benefiting the Boys & Girls Club of the Keys.

Dec. 5-8, 13-15: Nutcracker Key West. 

Key West. Audiences can discover the Florida Keys’ seafaring heritage, coral reef environment and holiday spirit during eight performances of “Nutcracker Key West.” The production gives the classic ballet a unique twist, transforming the well-loved tale of a young girl’s dream into a celebration of Key West’s culture, traditions and underwater wonders. Showtimes vary at the Tennessee Williams Theatre, 5901 College Road. Visit nutcrackerkeywest.com for tickets and more information.

Dec. 6: Wesley House Family Services Holiday Village and BeLighted Bike Ride. 

Key West. The annual family-friendly Holiday Village is set for 5-9 p.m. at the Coffee Butler Amphitheater at Truman Waterfront Park, 21 Quay Road, with community vendor booths, holiday-themed inflatable obstacle courses for kids, rides, food trucks, a “best bike” contest and photos with Santa. The bike ride, featuring a parade of bicycles decorated with holiday lights, leaves at 8 p.m. Tickets are $20 each (four for $70) for those age 4 and up, and free for kids age 3 and under. Visit wesleyhouse.org/events/belighted2024 or call 305-809-5000.

The BeLighted Bike Ride through Key West’s Old Town caps off the snowy, celebratory Holiday Village. Photo: Carol Tedesco

Dec. 6 and 13: Holiday Historic Inn Tours.

In this first of two holiday historic inn tours, explore four beautifully decorated locations and their unique architecture and history from 6 to 8 p.m. Sample sweet and savory holiday treats and libations. Locations are: Hemingway’s Social Club at Papa’s Pilar Distillery, Lighthouse Inn, Wicker Guesthouse, and the Gardens Hotel. The tours are self-guided. $40 tickets available online, but must be picked up after 5:30 p.m. on Dec. 6th at the first location, Hemingway’s Social Club at Papa’s Pilar Distillery, 210 Simonton St. The second inn tour takes place Dec. 13.

Dec. 7: Key West Hometown Holiday Parade. 

Key West. Holiday spirit is to fill the streets during the annual Key West Holiday Parade, showcasing the island city’s local charm with marching bands, school groups, motorized and non-motorized floats and lively community participation. The parade begins at 6:30 p.m. at Truman Avenue and White Street beside Bayview Park and proceeds down Duval Street. Seeing Santa is a highlight for kids. 

Key West’s Hometown Holiday Parade is always a festive, family-friendly event. Photo: Carol Tedesco

Dec. 8: Christmas on the Sheriff’s Animal Farm.

Stock Island. Children and adults are invited to visit the unique Monroe County Sheriff’s Office Animal Farm for a special holiday open house from 1-3 p.m. It’s located just northeast of Key West at 5501 College Road. Holiday donations are encouraged. Call 305-293-7300 for more information.

Dec. 8: Eaton Street Christmas Stroll. 

Key West. Eaton Street becomes a southernmost North Pole Sunday, Dec. 8. Wander the blocks between Whitehead and Simonton from 3:30-7 p.m., stopping at venues including St. Paul’s Episcopal Church at 401 Duval St. for a traditional Christmas concert, and Tropic Cinema at 416 Eaton St. for some classic cartoons. The Studios of Key West hosts an open house at 533 Eaton St. during the stroll. Visit tskw.org/eaton-street-christmas-stroll. 

Dec. 9-23: Old Town Trolley’s Holiday Sights & Festive Nights Tours.

 Key West. The popular green and orange trolleys, festively adorned with holiday lights, showcase Key West’s best-decorated neighborhoods, buildings and homes on fun-filled 60-minute excursions. Tours depart each evening from Mallory Square at 6:30, 7, 8 and 8:30 p.m. Visit trolleytours.com/key-west/christmas-holiday-tours or call 855-623-8289 or 305-296-6688.

The Old Town Trolley and Conch Train Holiday sights & Festive Nights tours take passengers through Key West’s best-decorated neighborhoods. Photo: JoNell Modys

Dec. 9-10 and 13-23: Conch Tour Train’s Holiday Sights & Festive Nights Tours. 

Key West. Lively Conch Tour Train tours depart from Key West High School, 2100 Flagler Ave., at 6:30, 7, 8 and 8:30 p.m. Included are holiday lights glasses as keepsake items. The hourlong tour, with holiday caroling, takes riders past the island’s most elaborately decorated houses, buildings and neighborhoods. Visit conchtourtrain.com/key-west-christmas-holiday-tours/ or call 305-707-5775 or 305-296-6688.

Dec. 11: Gay Key West Holiday Lights Trolley Tour. 

Key West. Dress in festive gear and join the Holiday Lights Trolley Tour for a night of dazzling holiday displays around Key West. The event begins with a jingle-and-mingle at Bobby’s Monkey Bar at 5:30 p.m., with the trolley’s departure at 6:30 p.m. for a two-hour tour and a few merry stops. Participants are encouraged to bring holiday treats to share. The tour ends around 8:30 p.m. at Bobby’s. Registration is required. Visit facebook.com/events/918157406915499. 

Dec. 13: Key West Art & Historical Society: Holiday Concert & Bazaar. 

Key West. Join the Key West Art & Historical Society for the 7th Annual Holiday Concert & Bazaar set for 5-9 p.m. on the historic verandah and street in front of the Key West Museum of Art & History at the Custom House. This popular event features some of Key West’s finest artisans, musicians, and choirs, including live holiday music from the Bahama Village Music Program’s Joyful Voices Choir and House of Pan Steel Pan Drums ensemble. Attendees can also enjoy food, libations, and a holiday light show by Key West High School’s Conch 5 Studios, projected onto the exterior of the Custom House. The event is free and open to the public. 281 Front St. Visit kwahs.org/bazaar.

The annual Holiday Concert & Bazaar includes a projected light show on the exterior of the historic Custom House. Photo: KWAHS

Dec. 13, 14, 15, 28: Lighted Boat Parades. 

Stock Island, Key Largo, Key West, Key Colony Beach, Little Torch Key. Festively decorated boats are set to cruise the waters around the Florida Keys, creating dazzling holiday spectacles. For details on the Stock Island Holiday Lighted Boat Parade (Dec. 13), visit keywestrotary.com. For the Key Largo Boat Parade on Blackwater Sound, themed “Christmas in the Keys” (Dec. 14), visit keylargoboatparade.com. For the Schooner Wharf Bar Lighted Boat Parade around the Key West Historic Seaport and harbor (Dec. 14), visit schoonerwharf.com. For the Key Colony Beach Christmas Boat Parade (Dec. 15), call 518-859-5662. For Kiki’s Sandbar Holiday Boat Parade and Drone Show on Little Torch Key (Dec. 28), call 305-780-7753.

Festive lighted boat parades are planned throughout the Keys island chain, including the one shown here on Key West Harbor. Photo: Carol Tedesco

Dec. 13 : Key West Outdoor Movies – Nightmare Before Christmas

Join us on Friday the 13th of December at Fort East Martello for a free outdoor movie night for an especially spooky Key West Christmas !  “The Nightmare Before Christmas” is often seen as both a Halloween and a Christmas movie, which is part of its charm. The film, directed by Henry Selick and produced by Tim Burton, blends elements of both holidays. Halloween Themes: The movie is set in Halloween Town and centers around Jack Skellington, the Pumpkin King, and other spooky characters. It opens with Halloween celebrations and has a dark, eerie aesthetic typical of Halloween.

Christmas Themes: The main plot involves Jack discovering Christmas Town and trying to take over the Christmas holiday. Many scenes focus on Christmas decorations, gift-giving, and Santa Claus, making it fit within the Christmas spirit too.

Because of this mix, it can be enjoyed during either holiday—or both! Fans often debate, but it’s widely accepted that it can be appreciated for both Halloween and Christmas.

Enjoy delicious food from our vendors, including fresh-squeezed lemonade, frozen treats, and all your favorite snacks. Plus, don’t forget the free popcorn, courtesy of First State Bank of the Florida Keys which benefits the Key West High School!  Don’t miss out on this wonderful community event. We can’t wait to see you there!

Invite your friends, bring your blankets and chairs, and let’s make this outdoor movie night one for the books! Don’t forget to share this post and spread the word. It’s going to be a blockbuster season, and we can’t wait to see you there!

Time: Doors at 5Pm. show at Dusk
Location: The Parade Grounds at Fort East Martello.
3501 S Roosevelt Blvd, Key West, FL 33040

There will be food and drink vendors, FREE popcorn, activities and MORE!

The Parade Grounds will open at 5:00 Pm. The Vendors will be there ready for hungry movie-goers! Feel free to come by, grab some food and pick a good spot!

Dec. 13-28: Waterfront Winter Wonderland. 

Key West. The Waterfront Winter Wonderland transforms the Coffee Butler Amphitheater at Truman Waterfront Park into a festive holiday experience for all ages. The family-friendly event features an ice-skating rink, rides like a Ferris wheel and carousel swings, games, live music, light displays and more. The amphitheater’s vendor village offers food and local artisan goods perfect for holiday shopping. Enjoy visits with Santa, a kids’ craft tent and festive celebrations. Admission is $12, with children 5 and under free. Additional costs apply for ice skating and rides. The fun takes place at 21 Quay Rd. Visit waterfrontwinterwonderland.com.

The Waterfront Winter Wonderland transforms the Coffee Butler Amphitheater at Truman Waterfront Park into a festive holiday experience for all ages. Photo: Nick Doll

Dec. 14: A Positive Step 5K Rudolph Red Nose Run. 

Key West. Dress in festive holiday pajamas for the 15th annual A Positive Step 5k Rudolph Red Nose Run. Open to runners and walkers of all ages and abilities, the race starts and finishes at the Southernmost Beach Café, 1405 Duval St. Check-in begins at 7 a.m., with the race starting at 8 a.m. Registrants receive a free T-shirt. Visit apsmc.org  for information.

Dec. 15 : Cold Full Moon Holiday Ride

For the Cold Full Moon Lighted Bike Ride we are meeting at the end of Edward B. Knight / White Street Pier at 5:30pm, we ride at 6pm Sunday, 12/15/24. Come out to catch sunset at 5:41pm and the full moonrise with us as we have fun riding and socializing.
Come dressed holiday festive (whatever you celebrate at this time of year) to celebrate Cold full moon.
Please use as many lights on your bike as possible: regular bike lights, decorative bike lights, wheel lights, novelty light-up hats, necklaces, tutus and anything that lights up or glows and is safe to ride with! If you have any bike-mounted music, you can bring that too. Don’t have that stuff? You can still come and ride.
Route is TBA. If you’re late, you can usually find the group here: http://glympse.com/!SSR

Remember that all ages and abilities are welcome to join the Southernmost Slow Riders. Ride at your own risk. No road closures, no “corking”/ using a biker to stop oncoming /cross traffic, no escorts, only informal marshaling — this is a mellow ride with friends you know and some you haven’t met yet. We will “take the lane” and own the road at times, but we will also get in single file or pull over to allow backed-up cars to pass or cross, so please follow the marshals and the general vibe of the group.

Dec. 15 : Snowy Day | Children’s Winter Concert

If you’ve missed this wonderful event in the past, let’s get it on your calendar now. Join us in the Garden Noon-2 p.m., Sunday, Dec. 15.

Featuring nationally known musician, Key West’s own Belle Jampol, our Snowy Day Winter Concert For Children has become one of the holiday’s most enjoyed events.

Designed for children of all ages and their families, the afternoon includes music and holiday activities in the exquisite Key West Tropical Forest & Botanical Garden.

Tickets are available at the gate and no advance registration is required. Tickets are $10 per family. (Botanical Garden Society members are free.)

This year, in addition to the concert, we will have holiday crafts for the kids, snow cones, a raffle and food and beverages for the entire family.

For additional information, contact Jennifer Fogarty, education@keywest.garden

Key West Lighting of the Menorah

The City of Key West’s annual Lighting of the Menorah ceremony takes place at Bayview Park Sunday, Dec. 29 from 5 to 7 p.m. 1320 Truman Avenue.

The annual Key West Home Tours feature lovely homes and gardens reflecting the varied tastes and originality of their owners.  You will be enchanted by exquisite restorations, creative renovations and delightful interiors featuring art collections, antiques, and much more.  305-294-9501 for information and tickets or visit

the Oldest House Museum Store, 322 Duval Street.

Thanks for your interest in Key West during the Holidays. This is a wonderful time of year to visit our special island. We hope to see you on Key West for the Holiday Season 2024 and to ring in 2025!

Visit HERE for our list of some of the best

New Year’s Celebrations on the island!