Terrific Ways to Spend the Holidays in Key West

Tired of the cold? We get it! It’s time to try something new and different this holiday season. Celebrate the holidays in Key West this year!

While our sunny shores may not be the first thing that comes to mind when you think about the holiday season, many people enjoy spending their holidays in Key West! We have several annual traditions that keep guests coming back year after year. Let’s explore some of our favorite ways to spend the holidays in Key West!

Key West Holiday Fest

Starts: November 25, 2026

Key West Holiday Fest is the umbrella event that brings together our favorite holiday celebrations in Key West. In fact, quite a few of them are included on our list! From holiday parades and tours to artisan markets and New Year’s Eve Celebrations, Key West Holiday Fest is your ultimate guide to celebrating the holidays in Key West. Follow along for all of their exciting excursions!

Nutcracker Key West

Showtimes: December 3-7, 2026

You can’t miss out on this holiday classic! The Nutcracker Key West combines the classic tale we know and love with fresh, exciting aspects specific to Key West. Instead of a snowy winter wonderland, the Nutcracker Key West is set in a tropical island paradise!

Watch as local Key West community theater players join professional dancers for this enchanting endeavor. It’s more than just a show; the Nutcracker Key West has become a beloved annual tradition!

Schooner Wharf Annual Lighted Boat Parade

Date: December 12, 2026, 8 PM

The annual lighted boat parade is another can’t-miss holiday tradition in Key West! You’ve seen holiday parades and Christmas lights before, but have you ever seen a lighted boat parade?

Back for its 35th year in 2026, it’s safe to say this beloved parade has become a staple in the community. Start your night off with festive music along the Harbor Walk, and get ready for the parade at 8!

You’ll see decked-out boats of all sizes, from schooners down to kayaks. The Key West community is creative—the boats feature Key West-inspired designs like palm trees, sea creatures, and even the Grinch. The whole night feels like a holiday wonderland, with seasonal treats, Santa’s sleigh, and a traditional ham dinner at Schooner’s. Experience the magic!

Key West Hometown Holiday Parade

Date: December 5, 2026, 7 PM

There’s no better way to ring in the holiday season than a classic holiday parade! Like most events here, our Key West Holiday Parade has its own unique flair.

The Key West Holiday Parade starts on Truman Avenue and proceeds down Duval Street. Be there to see holiday floats, community groups, and of course, the guest of honor, Santa Claus himself!

Wesley House Holiday Village & BeLighted Bike Ride

Date: December 4, 2026, 5 PM

For a more family-friendly time in Key West, head to the Coffee Butler Amphitheater for the annual Holiday Village and BeLighted Bike Ride! Enjoy carnival rides, games, food trucks, and holiday activities before riders experience the magic of riding their bikes, fully equipped with festive holiday lights.

Custom House Holiday Concert & Bazaar

December 11, 2026, 5 PM

Get into the holiday spirit at the annual Custom House Holiday Concert & Bazaar! Held at the Key West Museum of Art & History's front porch, this seasonal celebration brings together holiday music and shopping in a festive setting, combining art, music, and food for all to enjoy! Stop by for an evening of holiday fun and enjoy another side of Christmas in Key West! Get some early Christmas shopping done at this event, featuring a variety of vendors offering handcrafted jewelry, clothing, textiles, and home décor.

Celebrate New Year’s Eve in Key West!

You’ll love New Year’s Eve in Key West! The island knows how to throw a party, and December 31, 2026, is packed with quirky, fun-filled celebrations you won’t want to miss. Head to Sloppy Joe’s Bar to watch a giant conch shell drop at midnight—a Key West twist on the classic ball drop.

Over at Bourbon Street Pub, things get fabulous with the famous Shoe Drop, where a glamorous drag queen descends in a sparkling red high heel. For a dash of pirate fun, check out Schooner Wharf Bar, where a pirate wench makes a grand entrance, lowered from the mast of a schooner. Each event has its own lively vibe, making it easy to find your perfect way to say hello to 2027.

Key West’s New Year’s Eve events are all about good times and great memories. Get there early to snag a good spot, grab a drink, and join in the countdown. With warm weather, unique traditions, and plenty of laughs, there’s no better place to kick off the new year. Cheers to starting 2027 the Key West way!

Book Your Holidays in Key West Directly with Dwell!

Featured: ROYAL PALM SUITE @ Travelers Palm Inn

Well, there you have it. We told you Key West was a wonderful place to spend your holidays!

When you book your Key West holiday stay, make sure you choose the best accommodations around! Our boutique hotel rentals near Duval Street offer a great location and top-tier amenities, including pools and full kitchens.

You can stay in the Truman Room or the Hemingway Suite while you’re here and immerse yourself in Key West History. No matter where you stay, you can’t go wrong when you book with us.  Browse our available boutique rentals near Duval Street, and book your holiday Key West rental directly with Dwell Key West!