Best Holiday Events in Key West


Best Holiday Events In Key West

The most magical time of the year is upon us and Key West is getting all decked out for the holidays by hosting festive events by land and sea and Santa sightings in between. Instead of let it snow we say let it glow as the lights and animated displays decorate the island during the season. Here are a few of our favorite holiday happenings in Key West:


Key West Annual Holiday Parade | Saturday, December 3rd 7pm

This is our hometown parade, and a local favorite, where the marching bands, floats and community groups bring the very young and the young at heart together for the holidays. Children sit curbside, with eyes wide open, patiently waiting for Santa’s arrival catching candy and goodies from parade floats.  The parade starts at 7pm at Truman Avenue and White Street, proceeds down Truman to Duval, where it takes a right and continues on to Eaton Street.


26th Annual Lighted Boat Parade | December 10th, 8pm

Deck the hulls and another holiday happening in Key West you don’t want to miss. The Lighted Boat Parade is a sea of lights shining bright and a big family affair as spectators hang out on the docks at Key West Harbor to view the decorated vessels – including but not limited to – kayaks, fishing vessels and classic schooners.  Head down to Schooner Wharf early as you don’t want to miss the Christmas tunes performed by the local Gerald Adams Elementary School Steel Your Heart Band at 6pm followed by the The Doerfels, an incredibly talented family who will be singing more of your holiday favorites.  Visit Schooner Wharf Bar to learn more about the Lighted Boat Parade Festivities.

Caroling on the Conch Train – Tours start December 7th through December 22nd

Holiday Light Tours of the island. All aboard the Key West conch train for an hour tour that takes you to the islands most elaborately decorated houses and neighborhoods while caroling through the streets of Key West.  A fun, festive event for everyone and you’ll see how decked out Key West really gets during the holidays.  Price: $14 for adults • $7 for kids (4-12) • Under 4 ride free.  Visit Key West Holiday Light Tours to learn more.


Lighted Bike Parade | Wednesday, December 7th at 7pm

Dress up and decorate your bike for a good cause. The Lighted Bike Parade is benefit for Wesley House Family Services that helps to gather the needed toys for the struggling, working families of Key West for the holidays.  All participants are asked to bring an unwrapped toy for the toy drive.   It’s nice to see the streets of Key West lit up with families and individuals with lighted, animated and decorated bikes.  Learn more about the Lighted Bike Parade by visiting Wesley House.


Nutcracker Key West | December 10 – 18, 2016

It’s the Nutcracker Ballet with a Key West twist! This special holiday tradition lives in the hearts and memories of all that participate as well as attend.   Performing on stage at Nutcracker Key West are principal dancers from the Russian National Ballet to the smallest chicken, from the gardens of Key West to our coral reef.   Local children and families, along with 15 professional dancers from around the world, will join together to perform this holiday theatrical production.  This historical recreation and Key West’s version of the Nutcracker is a truly magical Key West event you don’t want to miss.  It is a must -do and see during the holidays.   To learn more and purchase tickets visit Nutcracker Key West



Photo Credit: Andy Newman

Ring in the New Year Key West StyleDecember 31st

A Pirate Wench. A Conch Shell. A High Heel Shoe Drop. We don’t just have a ball drop to ring in the New Year, we’ve got Sushi dropping from a High Heel Shoe at Bourbon Street Pub, a Pirate Wench descending from a tall ship at Schooner Wharf, and a Conch Shell drop from Sloppy Joe’s, one of the most famous bars in Key West.


Santa Sightings at Southernmost!

We saved the best for last. Whether you’re on the naughty or nice list we just want to say Happy Holidays from our family to yours.  Don’t be surprised if you see Santa at Southernmost 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.



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