Thinking about celebrating the holidays in Key West? Here, the season bursts with island flair and festive fun at every turn. Picture merry markets on the beach, parades by land and sea, a winter wonderland featuring an ice-skating rink, and a Nutcracker ballet with a Key West twist. And yes, there’s even a Christmas Headquarters in the Southernmost City! From lighted bike and boat parades to a hometown holiday celebration and New Year’s Eve like no other, Key West reinvents holiday traditions in its unforgettable style. Celebrate with family and friends, both new and old, and maybe you’ll discover a new tradition right here with us. Dive into the magic of the season—here’s your guide to all the festivities you won’t want to miss! Photo courtesy of Rob O’Neal.

Holiday Events in Key West

November 27: The Lighting of the Key West Harbor Walk of Lights

Festivities begin at 5 pm, with lighting at 6 pm

Start your holiday season with the Lighting of the Key West Harbor Walk of Lights! Join locals and visitors at the Harbor Walk plaza at Greene and Elizabeth Streets for the 2024 lighting ceremony. Witness the transformation of the Historic Seaport into a stunning holiday wonderland, with creative displays celebrating Key West’s maritime history. Enjoy live music starting at 5 PM, with the official lighting taking place at 6 PM. The lights will stay up through New Year’s Eve, making it the perfect spot for a festive stroll by the Seaport all season long.

December 5 - 8 and 13 -15: Nutcracker Key West

This December, Nutcracker Key West returns to bring tropical flair to the classic ballet, performed every other year. Experience this enchanting production that reimagines The Nutcracker with island-inspired touches, featuring chickens, roosters, sea fans, anemones, and even a conch shell. With costumes and set designs reflecting Key West’s natural beauty, this holiday tradition creates unforgettable moments for families. Performances are held at the Tennessee Williams Theater, 5901 College Rd.

Show Dates: December 5-8 & 13-15 (Showtimes vary)

Learn more about Nutcracker Key West.

December 6: Holiday Village & BeLighted Bike Ride

At the Coffee Butler Amphitheater

Gather family and friends for an evening of holiday cheer at the Holiday Village at Coffee Butler Amphitheater. Enjoy carnival rides, games, and festive booths offering food and holiday treats. When night falls, Key West lights up with the BeLighted Bike Ride, where locals decorate their bikes with holiday lights and decor and parade through the streets in bright costumes. Photo courtesy of Carol Tedesco.

The BeLighted Bike Ride starts at 8 p.m. and departs from the Coffee Butler Amphitheater, 21 Quay Rd. Admission is $20 per person, or four tickets for $70. Children aged three and under enter free.

Learn More About the Holiday Village & BeLighted Bike Ride.

December 7: Key West Holiday Parade

The parade starts at 7 pm.

Get ready for one of the island’s favorite holiday traditions—the Key West Holiday Parade! As floats decked out in festive flair roll by and marching bands fill the air with cheerful tunes, the holiday spirit truly comes alive. Families line the streets, kids with wide eyes eagerly reaching for candy tossed from the creatively designed floats, all while waiting for Santa to make his big entrance. If you’re wondering where the locals go to celebrate, look no further! This is the place to be. The parade kicks off at 7 PM at Truman Avenue and White Street beside Bayview Park, making its way down Duval Street—so grab a spot along the route and get ready for a parade that will create merry memories you’ll cherish forever!

December 8: Merry Marketplace & Sandman Building Competition

At Southernmost Beach Resort, 10 AM - 3 PM

Join us for a joyful day at the Merry Marketplace at Southernmost Beach Resort! Explore unique gifts from local artisans while enjoying live music that sets the festive mood. Kids can channel their creativity in the Sandman Building Competition, where they’ll put a Key West twist on the classic snowman—think sandy sculptures instead! Santa will be on hand for photo ops and holiday cheer. We welcome you to a no-snow zone with the stunning backdrop of the Atlantic Ocean, making this the perfect opportunity to soak up the holiday spirit and shop for unique gifts in paradise!

December 8 - 23: Holiday Sights & Festive Nights Tour

Departs from Mallory Square

Hop on the Old Town Trolley for a magical ride through Key West’s most decked-out neighborhoods! This tour takes you through streets glowing with holiday lights and elaborate decorations as locals go all out to bring the season to life. Sit back, relax, and let the trolley guide you through these sparkling sights, complete with fun narration full of quirky Key West facts and local stories. It’s the perfect way to soak up the island’s holiday magic—no walking required! Photo courtesy of Old Town Trolley.

Tickets: Adults $36.28, Children $24.53

Learn more about the Holiday Sights & Festive Nights Tour.

December 13 - 28: Waterfront Winter Wonderland

4 pm - 10 pm | Truman Waterfront Park

Bring the family to the 2nd Annual Winter Wonderland in Paradise at Truman Waterfront Park! Experience an enchanting evening with an ice-skating rink, dazzling holiday lights, games, live music, and more. Browse handmade crafts at the holiday market, sip on hot cocoa, and enjoy a festive slice of paradise, Key West-style.

Admission and Fees

Wonderland Admission: $10 (children five and under free)

Includes visits with Santa (through 12/22), a kids' craft tent, letters to Santa station (through 12/22), live entertainment, a Christmas train, photo opportunities, inflatable snow globes, a holiday market (Saturdays and Sundays), and daily snow flurries. Tickets are available for purchase online or at the door.

Unlimited Ride Wristband: $35 (single-day use)

Unlimited ride wristbands and individual ride tickets are available for purchase at the venue. 

Rides Include: Ice skating, a carousel, giant slide, carousel swings, Ferris wheel, scrambler, and Christmas train. 

Learn more about Winter Wonderland in Paradise.

December 13: Holiday Concert & Bazaar

At the Custom House Museum, 5 PM - 9 PM

Join us for a night of festive fun at the Holiday Concert & Bazaar! Located at the historic Custom House Museum, this delightful event brings together live music, local artisans showcasing unique gifts, and seasonal drinks to warm your spirits. Don’t miss the enchanting light show projected onto the museum’s iconic red-brick exterior—it’s a sight to behold! Best of all, this celebration is free and open to the public, making it the perfect way to soak up the holiday cheer with family and friends. Join us at 281 Front St. for an unforgettable evening of holiday magic!

December 14: Schooner Wharf Bar Lighted Boat Parade

Location: Schooner Wharf and Key West Harbor

Get ready for the 33rd Annual Schooner Wharf Bar/Absolut Vodka Lighted Boat Parade! As the sun sets, the harbor transforms into a sparkling spectacle with boats decked out in dazzling holiday decor. The festivities kick off at 8 PM, but you’ll want to arrive early at 6 PM to soak up the live music from the Bahama Village Music Program's steel band. Gather your friends and snag a spot by the waterfront to cheer on the beautifully lit vessels as they cruise through the harbor—this is one Key West tradition that’s pure holiday magic! Hang out by Schooner Wharf for all the action. Photo courtesy of Carol Tedesco/Florida Keys News Bureau. 

December 18: Christmas Trivia & Cookie Swap

Location: The Christmas Headquarters at The Parlour at Avalon (1317 Duval Street)

Get into the holiday spirit with an evening of Christmas Trivia and a festive Cookie Swap. Test your knowledge on holiday topics and indulge in homemade cookies from locals. It’s a fun way to celebrate the season and meet new friends.

December 21: Queen of Christmas Pageant & Community Swim Night

Location: Southernmost Beach Resort, Shores Pool, 6 PM

Join the fun at the Queen of Christmas Pageant! Local women aged 40+ compete for the crown in categories like Best Glamour Christmas, Best Country Christmas, and Best Key West Christmas. Held poolside at Southernmost Beach Resort’s Shores Pool, the pageant is followed by a community swim night to celebrate the newly crowned Queen of Christmas.

December 24: 5th Annual Holiday Cookie Throw-Down

Location: The Marker Key West Harbor Resort, 12 PM

Celebrate Christmas Eve at The Marker’s 5th Annual Holiday Cookie Throw-Down. Local bakers compete to create the best holiday cookies, and guests get to sample and vote for their favorites. It’s a sweet way to indulge in the season and join in some friendly holiday competition.

December 26: 4th Annual Holiday Candy Cane Hunt & Kids Party

Location: Southernmost Beach Resort, 3 PM

The holiday fun continues with the Candy Cane Hunt & Kids Party at Southernmost Beach Resort. Kids will love searching for candy canes and participating in slime stations, Legos, and coloring activities, while adults can enjoy food and drink specials in a relaxed beach setting. 

December 29: Circus of the Sea: ELF Edition

Location: Southernmost Beach Resort

Get ready for Circus of the Sea: ELF Edition—a one-hour, pirate-themed acrobatic and aerial show. Featuring stunts, trampolines, and funny skits, this family-friendly performance is packed with holiday spirit and excitement. Your ticket includes access to the Pineapple Pool for a pre-show pool party.

Tickets: $30 - Purchase Tickets Here

Learn more about Circus of the Sea: Elf Edition.

December 31: New Year’s Eve Celebrations in Key West

Ring in the New Year, Key West style! Get ready for an unforgettable night featuring the iconic Conch Shell Drop at Sloppy Joe's, the Pirate Wench Drop at Schooner Wharf, and the fabulous Drag Queen in a Red Stiletto Drop at 801 Bourbon Street. Each celebration brings its own unique twist to the countdown, drawing thousands together to kick off 2025 in paradise—a New Year's Eve experience you won't want to miss!

The Christmas Headquarters at The Parlour at Avalon

Make sure to visit The Christmas Headquarters at The Parlour at Avalon, hosted by Southernmost Beach Resort. Open Tuesday through Saturday until January 3rd, this cozy hub offers a lineup of fun weekly activities that embrace the spirit of the season. Join us for ornament-making, festive trivia, and our popular Ugly Christmas Sweater Night, where donning your most festive (or delightfully ugly) attire earns you a free drink! Located at 1317 Duval Street, it’s the ultimate destination to immerse yourself in the holidays.

Weekly Activities:

●      Tuesdays: Ornament Making, 3 PM - 9 PM

●      Wednesdays: Christmas Trivia, 8 PM - 9 PM

●      Thursdays: BOGO Candy Cane Shots, 3 PM - 9 PM

●      Fridays: Ugly Christmas Sweater Night (free drink with a sweater!), 3 PM - 9 PM

From trivia and crafts to festive drinks, our holiday-themed events at The Parlour at Avalon make it your go-to destination for seasonal fun in Key West.

We invite you to unwrap the magic of the season with us in paradise. The Marker Key West Harbor Resort and our sister property, Southernmost Beach Resort, wish you a holiday filled with warmth, joy, and a season that’s merry, bright, and full of wonder and delight. May your holidays be tree-mendously joyful! Happy Holidays! #lovethemarker