Best Holiday Events In Key West 2017

The most magical time of the year is once again upon us and Key West is all decked out for the holidays.  There will be caroling, holiday house tours, concerts, shopping with local artisans, 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:


Conch Train Holiday Lights Tour | Now through December 23rd

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.  A fun, festive event for everyone and you’ll see how decked out Key West really gets during the holidays.  Price: $15 for adults • $7 for kids (4-12) • Under 4 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


Lighted Bike Parade | Wednesday, December 6th

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.  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 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.


Studios of Key West Holiday Artisan Market | December 9th

Holiday Shopping with the locals!  Over 20 artisans will come together at the Studios of Key West to present unique and locally produced gifts, jewelry, textiles, home accessories and quality crafts.  The artisan market is scheduled from 9am to 2pm at The Studios of Key West, 533 Eaton Street.


Schooner Wharf Bar/ Absolut Vodka Lighted Boat Parade | December 9th, 8pm

Visitors and locals come together at the Key West Harbor for the Schooner Wharf Bar/Absolut Vodka Lighted Boat Parade. The parade features decorated vessels (including but not limited to – Kayaks, fishing vessels and classic schooners, parading through Key West historic harbor.  The Lighted Boat Parade starts at 8pm but we recommend you head down to Schooner Wharf Bar early as you don’t want to miss the the Christmas tunes performed by the local Gerald Adams Elementary School Steel Your Heart Band at 6pm and there will be live music throughout the evening.   Visit Schooner Wharf Bar to learn more.


Monthly Artisan Market | A Holiday “Shop Local” Edition | December 17th

Sunday morning head over to the parking lot of the Restaurant Store located at at 1111 Eaton Street.  Yes, that’s where this colorful, vibrant, eclectic group of artisans come together to sell unique works of art and more.  The open-air bazaar is filled with Keys artists, chefs, authors, craftspeople and performers.  The market is open to the public from 10am – 2pm every third Sunday of the month.


2nd Annual Holiday Concert and Bazaar at the Custom House Museum | December 21st

There will be local artisans showcasing their wares, musicians and choirs along with a spectacular holiday light show and of course “selfies” with Santa.  The event is from 5-9pm at the historic Custom House Museum located at 281 Front Street.


58th Annual Key West House and Garden Tours | December 27th

This is a self-guided tour showcasing festively dressed Key West homes and gardens.  Tours are from 3-7pm.  Tickets are $30 in advance and $35 day-of-tour.  All proceeds benefit the Old Island Restoration Foundation museum and programs.  Learn more about Old Island Restoration Foundation and the tours.

Ring in the New Year in Key West Style – December 31st

A High Heel Shoe Drop. A Pirate Wench. A Conch Shell.   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 Bar, and a Conch Shell drop from the iconic Sloppy Joe’s Bar.  Thank goodness this is a small island because the good news is you can visit all three locations during the night.


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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