Christmas in the Florida Keys is calling! There’s truly nothing like a Key West Christmas to bring holiday cheer to you and your loved ones. If you’re worried that Christmas in Key West won’t feel as cozy as Christmas back home, rest assured that the island will be all aglow with holiday lights from creative holiday displays and live holiday music performances.
There are so many special holiday events to discover! If you want to spend this holiday season in Key West, it’s time to start planning your trip. Grab a frozen hot chocolate, put a little sunscreen in your stocking, and take notes as we share tips for planning a perfect Key West Christmas!
A tour we think you'll love
1) Have A Merry Time At The Key West Christmas Tree Lighting At The Historic Seaport
Christmas trees work a little differently here in Key West compared to the rest of the country. The big “tree” is actually a giant tree-shaped structure made of lobster traps that’s perched at Key West Bight Marina! Come celebrate the tree at the annual Bight Before Christmas Celebration at the Historic Seaport. “Bight” refers to a bend in the shoreline at the harbor.
The big lobster trap Christmas tree lighting typically takes place the Wednesday before Thanksgiving. Lights come on at 7 p.m. at the Margaret Street Plaza at Old “Land’s End Village”. Guests can arrive at 6 p.m. to enjoy merriment and cookies!
2) Give The Gift Of A Boat Trip In Key West
Here’s a great gift idea if you want to treat your partner or family to a special surprise after you arrive in Key West. Book a Key West sandbar tour that will make you feel like you’re floating through a real-life postcard!
Key West Boat Trips takes you to a part of the Florida Keys that’s unlike anyplace else. Float along dreamily without a crowd in sight as our experienced captains bring you to Key West’s best sandbars for some time to relax and connect with your loved ones. Itinerary options include:
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Sandbar Hopping – Enjoy a 25-minute ride to the sandbars to enjoy the magic of Mud Keys and Snipe Point.
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Key West Sunset Cruise – Relax beneath a tangerine sky before arriving at a sandbar where you’ll be free to wade in the water or relax in the sand.
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Mud Key Mangrove Safari – Enjoy the excitement of zipping through backcountry waters before arriving at Mud Key sanctuary to take in views of nature few ever see!
We offer the best small-group boat fleet in the area! Our experienced captains will ensure that your itinerary meets your needs. If you’re looking for a special holiday treat in Key West, book your unforgettable adventure with us!
3) Enjoy Sparkling Holiday Lights At The Key West Harbor Walk Of Lights
Operating nightly starting at 6 p.m. from the night before Thanksgiving through New Year’s Eve, the Harbor Walk of Lights covers three blocks of holiday lights and festive displays start at the plaza at Greene Street and Elizabeth Street.
The holiday music pops on at Harbor Walk at 5 p.m. to let you know something fun is coming! The colorful displays that line the Harbor Walk of Lights tie into the maritime history of Key West and the Historic Seaport.
You don’t want to miss the Harbor Walk experience if you want to get into the holiday spirit while visiting Key West!
4) Cheer On The Boats At The Schooner Wharf Lighted Boat Parade
Taking place the second week of December, the annual lighted boat parade at Schooner Wharf on the Key West waterfront is one of the biggest Key West holiday celebrations. While the boats set sail at 8 p.m. sharp, you’ll want to arrive at 6 p.m. for family fun along the glowing Harbor Walk.
Here’s how to enjoy the boat parade:
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Check out boats all decked out in lights and holiday-themed decorations. Vessels in the parade range from large fishing vessels and classic schooners to kayaks decorated with string lights.
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Cheer boats on as a spectator on the docks as the colorful parade passes. Parade participants toss beads and treats to children from their boats!
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Pick up a conch shell Christmas ornament from a local vendor.
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Wait for Santa’s sleigh to roll up to the judge’s stand!
While this is a kid-friendly event, you don’t have to visit Key West with the family to attend. Many people who come for the parade dip into Schooner Wharf Bar afterwards for some eggnog and other seasonal libations.
5) Chase The Holiday Spirit At The Key West Hometown Holiday Parade
Taking place the first weekend in December each year, the Key West Hometown Holiday Parade is the most charming hometown parade! This after-dark parade begins at 7 p.m. The parade route begins on Truman Avenue at White Street before proceeding to Duval Street and ending on Eaton Street.
You can look forward to festive holiday floats and classic holiday music from local high school marching bands. Yes, Santa will even be making the trek down from the North Pole to the tropics to make an appearance!
6) Do Some Holiday Shopping At The Key West Artisan Market
Don’t miss the chance to get your hands on one-of-a-kind gifts when visiting Key West during the holiday season. Key West Artisan Market is open on select Sundays from November to April.
Located at Higgs Beach, the market is open from 10 a.m. to 2 p.m. on days of operation. Shoppers will find:
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Culinary goods
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Jewelry
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Wood art
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Crafts
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Textiles
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Books
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Fresh food and produce
As the gift that keeps on giving, the market donates a portion of proceeds to support local charities.
7) Have Fun While Doing Good At The Wesley House Family Services Holiday Village
The Holiday Village and BeLighted Bike Ride is one of the most beloved holiday celebrations in the Florida Keys. The event features more than 20 community booths featuring games, bounce houses, carnival rides, and treats from local restaurants and food trucks. Live performances are also in the mix! You can also snap a photo with Santa as “snow” falls over Key West!
During the BeLighted Bike Ride portion of the event, riders depart from the Coffee Butler Amphitheater at Truman Waterfront Park on the first Friday in December at 8 p.m. on bikes that are all lit up for the holidays!
Pro Tip: If you plan to attend this event when you visit Key West, planning is needed. Each ticket is $20 per person or four for $70. Kids 3 and under are free. Tickets include unlimited rides and bounce houses. All proceeds benefit Wesley House Family Services.
8) Attend The Free Holiday Classic Car Show
Rev up your engine for Christmas in Key West at the annual Holiday Classic Car Show hosted by the Florida Keys Southernmost Car Club.
Taking place in mid December each year, this festive show at the Conch Republic Seafood Company parking lot gives you an opportunity to see classic cars from multiple eras!
While entry is completely free, event organizers ask that attendees bring an unwrapped toy for the Monroe County Domestic Abuse Shelter.
9) See The Nutcracker Key West Rendition
One of the biggest treats of spending the holiday season in Key West is being able to attend a showing of a tropical version of the Nutcracker! This sunny take on a Christmastime classic is put on by the acclaimed Tennessee Williams Theatre.
In this island-style version, sugarplum fairies wear sea fans instead of tutus! Don’t miss your chance to be in the audience for a performance you will never forget.
10) Shop For Unique Christmas Goods At The Custom House Annual Holiday Concert & Bazaar
Hosted by the Key West Art & Historical Society, the annual Custom House Annual Holiday Concert & Bazaar offers an evening of vendors, food, music, and holiday decorations.
Built in 1891, the Custom House Museum is a famed landmark overlooking the harbor that houses two stories of artwork and cultural exhibits. Seeing the building all dressed up for Christmas is truly a treat you won’t want to miss!
11) Embark On The Old Town Trolley’s Holiday Sights & Festive Nights Tour From Mallory Square
This magical 60-minute Key West holiday experience takes you around on an Old Town Trolley bus to see historic Key West homes draped in cascades of holiday lights and decorations. Enjoy creative holiday displays as neighbors compete for a $500 first-place prize to have the most festive home in Key West!
Departing from Mallory Square the tour runs from Dec. 9 through Dec. 23. Check schedules and availability ahead of time to confirm dates for the current year. With tours starting after dark, you can even plan to see a gorgeous wintertime Sunset at Mallory Square if you arrive early.
12) Experience Holiday Magic At The Key West Butterfly And Nature Conservatory
Like the rest of the country, Key West mostly shuts down for Christmas. However, a few spots offer ways to celebrate if you’d like to plan a magical outing. One of those spots is the island’s famed butterfly conservatory!
The Key West Butterfly and Nature Conservatory on Duval Street is open from 9 a.m. to 2 p.m. on Christmas Eve and Christmas Day. Final tickets are sold at 1:30 p.m. both days. This amazing spot offers the opportunity to walk about hundreds of colorful, majestic butterflies and exotic birds.
13) Enjoy Delicious Christmas Day Treats
While spending Christmas in the Florida Keys is one of the most magical experiences you’ll ever have, you may be feeling a bit homesick for your own kitchen when it comes to holiday baking. Luckily, Key West has some amazing options when you want Christmas goodies!
Many restaurants are actually open on Christmas Day. Here’s a look at some that offer special Christmas dinner menus:
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Flagler’s Restaurant at the Casa Marina – Offers a Christmas Day buffet
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Cafe Sole – Offers an expansive Christmas Eve and Christmas Day dinner experience featuring specialties like slow-roasted goose, rib with black truffle, homemade stuffing, and more
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Hot Tin Roof Restaurant – Offers a reservation-only four-course feast for Christmas Eve or Christmas Day
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Matt’s Stock Island Kitchen & Bar at the Perry Hotel & Marina – Hosts Christmas Day brunch and dinner
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One Duval at the Pier House Resort & Spa – Hosts dinner on Christmas Eve and Christmas Day
Pro Tip: Christmas dinner spots in Key West fill up quickly! Book reservations ahead of time to ensure there’s a spot waiting for you!
Make Key West Your Home For The Holidays
At Key West Boat Trips, our top-notch customer service and reasonable rates make every voyage merry and bright for our guests! Let our knowledgeable captains help you plan the perfect experience this holiday season.
Ready to put a bow on it? Book your private Key West sandbar boat trip with Key West Boat Trips today!
