Best Holiday Events in Key West 2018

It really is the most magical time of the year and Key West is all decked out for the holidays. There will be caroling, holiday house tours, concerts, shopping, lighted boat and bike parades, Santa sightings, and celebrations to ring in the New Year. Here are a few of our favorite holiday happenings in Key West:

Lighted Bike Parade, Wednesday, December 5th Dress up and decorate your bike for a good cause and have loads of fun at the same time. The Lighted Bike Parade is a benefit for Wesley House Family Services that helps to gather the needed toys for the struggling, working families of Key West for the holidays. Participants are asked to bring an unwrapped toy for the toy drive (that’s part of the registration requirement.) It’s nice to see the streets of Key West lit up with families and individuals with bright lighted, animated and and decorated bikes. It all begins at Bayview Park with 6pm Check-In, 6:30 Helmet Fitting and Meet Santa, 7pm Bike Ride Begins. Learn more about the Lighted Bike Parade by visiting Wesley House.

Caroling on the Conch Train – December 7 through December 22nd Add this to your Holiday Bucket List – Conch Tour Train Holiday Lights (and Caroling) Tour. This is a one-hour special holiday tour at night that takes you to the island’s most elaborately decorated houses and neighborhoods while caroling through the streets of Key West. There will be lots of caroling along with cider and cookies. An added bonus are the special holiday lights glasses! Price: $17.85 for adults • $8.40 for kids (3-12) • Under 3 ride free. Visit Key West Holiday Light Tours to learn more or visit the concierge upon arrival to find out when the tours are running during your stay.

Key West Holiday Parade, December 8th, 7-9pm One of the best parades on the island is Key West’s hometown holiday parade where everyone gets in the spirit – there will be marching bands, groups, floats and children patiently waiting on the sidewalk for Santa to arrive. A fun family holiday event for everyone. The route proceeds down Truman Ave to Duval, where it takes a right and continues on to Eaton Street.

Best Holiday Events in Key West 2018

Nutcracker Key West – December 8-16

The Nutcracker with a Key West Twist! This special holiday tradition lives in the hearts and memories of all that participate, view, and give to this fantastic show. Nutcracker Key West is dazzling and unique with her tiny chickens, humorous roosters, lively shrimp, and brilliant jewels of the Atocha. A sumptuous, artful, theatrical experience wrapped as a perfect holiday gift for the Southernmost City – Key West’s very own NUTCRACKER! The Key West productions are complete with chickens, roosters, sea fans, anemones, and yes, even a conch shell. This is one of the largest productions to ever play on a Key West Stage! The performances are held at the Tennesee Williams Theatre. Buy Tickets

28th Annual Schooner Wharf Bar Lighted Boat Parade | December 15th, 8pm

Head over to the Key West Harbor for the Schooner Wharf Bar Annual Lighted Boat Parade. The parade features decorated vessels (including but not limited to – Kayaks, fishing vessels, and classic schooners, parading through the Historic Seaport. The parade starts at 8pm, but we recommend you head to the Seaport early as you don’t want to miss the children of Gerald Adams Elementary Steel Your Heart Band perform Christmas tunes at 6pm followed by live music and performances throughout the evening. Visit Schooner Wharf Bar to learn more.


Holiday Concert and Bazaar at the Custom House Museum | December 19th, 5-9pm

Oh, what fun!!! Get in the holiday spirit at the Key West Art & Historical Society’s Holiday Concert & Bazaar located on the porch and promenade of the Custom House Museum. The celebration will feature Key West’s finest artisans, musicians, and choirs, along with a spectacular holiday light show. The event is from 5-9pm at the historic Custom House Museum located at 281 Front Street.

59th Annual Key West House and Garden Tours | December 28th and 29th

This is a self-guided tour showcasing festively dressed Key West homes and gardens. Tours are from 3-6pm. Tickets are $35 in advance and $40 day-of-tour. All proceeds benefit the Old Island Restoration Foundation museum and programs. Learn more about Old Island Restoration Foundationand the tours.

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New Year’s Key West StyleDecember 31st

Celebrate the New Year in style – Key West style that is! There are so many colorful and creative ways to ring in the New Year in Key West. Here they are: Watch Sushi drop from a High Heel Shoe at Bourbon Street Pub on Duval Street, a Pirate Wench descending from a tall ship at Schooner Wharf Bar or watch the Conch Shell drop from the iconic Sloppy Joe’s Bar. You can visit all three locations during the night and celebrate with new and old friends as you ring in the New Year with us.

Santa Sightings at a Key West Beach Resort!

We saved the best for last. Of course, it’s a yearly tradition, and just because you are on vacation, it doesn’t mean Old Saint Nick won’t find you. Don’t be surprised if you see Santa at Southernmost Beach Resort hanging out in a hammock or sitting poolside sipping and spreading holiday cheer.

What are some of your favorite Holiday Events where you live? Share your favorite magical moments with us on our social networks using hashtag #somolife.