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

November 27th-December 31st, 2024

Key West Holiday Fest is the big umbrella event that holds 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!

Key West Harbor Walk of Lights

Nov 27th, 2024 - 5:00 pm to Jan 1st, 2025 - 10:00 pm

Who wouldn’t want to see a dazzling holiday light show? The Historic Seaport turns into an enchanting world of glowing lights and nautical-themed displays this time of year.

The show happens nightly from November 27th to January 1st, 5:00 PM-10:00 PM. Get there at 5:00 for festive music, and get ready for the big ceremony at 6:00! You can watch the waterfront come alive with gorgeous holiday lights and shimmering reflections representing Key West. This event has become a cherished piece of Key West’s holiday celebrations, and you won’t want to miss out!

Nutcracker Key West

December 1st-15th, 2024, Full Schedule of Performances

You can’t miss out on this holiday classic! The Nutcracker Key West combines the classic tale we know and love with fresh and exciting aspects local 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

December 14th, 2024, 6 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 a 33rd year in 2024, 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

December 7th, 6:30-10:00 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 Clause himself!

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, 2024, 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 goodbye to 2024.

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 2025 the Key West way!

Book Your Holidays in Key West Directly with Dwell!

Pictured: The Hemingway Suite at the Inn on Fleming

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 like rentals with pools and full kitchens.

We recently acquired a new property here at Dwell, the Inn on Fleming. Our newest addition is in a great location near the Historic Seaport, bars, restaurants, and famous Duval Street.

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!