Key West In December - 11 Exciting Things To Do During The Winter

Key West In December

Key West is one of the top vacation spots in the world that attracts the masses each season for its pristine setting and perfect weather. Snowbirds and college students alike who are looking to escape the harsh winter weather conditions often spend time in Key West as they look forward to a daily dose of sunshine and their feet in the sand.

When spending time in Key West In December, there are a few exciting activities to enjoy after you arrive at the Key West Airport, and look forward to your stay.

Old Town Trolley Tours, Duval Street

1) Watch The Lighted Boat Parade

When you’re traveling to Key West in December, you can still look forward to celebrating the holidays and participating in a variety of festive events and activities in the destination. If you want a unique perspective during the Key West parade, you can get tickets to sit aboard the America 2.0, which is a schooner that is a replica of the winning boat in America’s Cup in 1851.

This three-hour sailing adventure will give you a front-row seat to the lighted boat parade and get into the holiday spirit while sipping on hot cider and Christmas cookies. The parade is hosted near Historic Seaport and is a short walk from a Key West hotel where you’re staying. The festive party atmosphere in Key West will allow you to still enjoy the holiday season while taking a trip away from home.

Key West In December - Lighted Boat Parade At Historic Seaport

2) Get Tickets For The Conch Tour Train

Spending time on your winter getaway in Key West should include the Holiday Lights Tour on the Conch Tour Train, where you can visit multiple inns and historical buildings that are lavishly decorated for the holiday season throughout Key West. Since 1958, the train has been a staple in Old Town and stands out for its yellow exterior as it navigates the Key West area.

While hopping onto the train, you can enjoy an hour ride at night that consists of plenty of caroling and indulging in cookies and hot cider to embrace the most wonderful time of the year. It’s one of the best ways to meet other people and learn more about the history of Old Town while taking a magical and educational tour.

Conch Tour In Old Town Key West, Florida Keys

3) Attend The New Year’s Eve Celebration

When you’re planning to be in Key West in December, the New Year’s Eve Celebration is a great way to kick off the new year with thousands of other locals. The warm weather makes it possible to spend time outdoors celebrating in the streets, where a disco party is hosted at the Bourbon Street Pub. This is where you can enjoy ordering drinks and watching performances on the outdoor stage, where live music is playing throughout the night during one of the largest events of the year. You can watch the famous drag queen ‘shoe drop’ performance at midnight.

Before the clock strikes midnight, many people head to Sloppy Joe’s Bar on Duval Street to watch the Conch Shell Drop – a manmade concha shell starts to descend from the top of the roof. Duval Street is also home to a variety of other bars and eateries in downtown Key West and is also where the Key West holiday parade is hosted each year.

Schooner Wharf Bar is another hot spot on New Year’s Eve, where a pirate wench is lowered from the ship’s mast as cannons go off, creating an exciting moment when it becomes the new year.

Key West In December - New Year's Eve

4) Tour The Harry S. Truman Little White House

The Harry S. Truman Little White House is known as a living museum that continues to use the same types of Christmas decorations. When you visit Key West, you can look forward to viewing the museum’s elaborate collection of ornaments from the 1940s and 1950s.

There’s also a variety of Presidential Christmas cards on display with White House Collector ornaments available to purchase as a stocking stuffer during the holidays. Each ornament is customized design to honor the museum and its rich history in Key West.

Harry S. Truman Little White House, Key West, Florida Keys

5) View The Christmas Decorations On A Rented Bike

If you want to go at your own pace while viewing the Christmas lights and decorations that are on display in Key West, rent a bike from Eaton Bikes. Cruising through Old Town is a great way to spend your time while visiting Key West because it’ll allow you to explore and view large wreaths on storefronts and twinkling lights on historic inns.

The annual competition that is hosted in Key West in December causes many business owners to display lavish decorations in hopes of being awarded the winner. The decor draws attention to architecture that you may not have noticed while driving around Key West and will allow you to discover a few hidden gems of restaurants and small stores.

December In Key West - Christmas Decorations

6) Take A Holiday Historic Inn Tour

When you visit Key West in December, the Holiday Historic Inn Tours are self-guided and are a popular activity to enjoy viewing multiple properties. If you don’t want to get around on foot on the Key West tour, trolleys are available to transport you to each stop, enhancing the quality of the experience during your visit to Key West. At each location, you can learn more about the rich history through the innkeepers before snacking on a few appetizers.

As you look for things to do in Key West in December, the Historic Inn Tour will prove to be memorable. You can even have the chance to meet Santa on this self-guided tour as he lounges in a hammock at The Mermaid & The Alligator, proving he’s also a fan of Key West and enjoys a break from the North Pole.

Key West In December - Decorated Palm Trees

7) Explore The Key West Lighthouse

The Key West Lighthouse has been a staple in the local area since 1825 and has 15 lamps. Tours are available, which allow visitors to take 88 steps to the top and view the quarters where past keepers have lived.

Key West Lighthouse

8) Visit The Key West Aquarium

When you want to enjoy the ultimate experience in Key West, you can get a firsthand look at the different types of marine life in the area by visiting the local Key West Aquarium in Mallory Square.

The aquarium is south of Duval Street and has a variety of fish, sharks, alligators, stingrays, and turtles. The interactive activities and exhibits provide an educational experience as you view over 100 different species of marine life.

December In Key West - The Key West Aquarium

9) Experience Key West Butterfly And Nature Conservatory

Located near the Southernmost Point, the Key West Butterfly and Nature Conservatory is a top attraction in Key West, where you can view butterflies of all different sizes in a lush and beautiful setting.

When you’re ready for warm and beautiful weather in December, the conservatory is a great place to learn more about butterflies and have an educational experience.

Key West Butterfly And Nature Conservatory

10) Visit The Tennessee Williams Fine Art Center

When you’re looking for things to do in Key West in December, you don’t have to miss out on classic Christmas traditions while spending time in paradise. Every other year, the Tennessee Williams Fine Arts Center hosts a performance of the Nutcracker ballet where 15 professional ballerinas and 50 children, and many local performers are on stage.

Because the performance is only every two years, tickets are always in high demand, making it necessary to purchase them in the planning stages of your trip to Key West.

The Nutcracker Ballet, Closeup Of Ballerinas

11) Book A Boat Trip To Enjoy Key West In December

You can enjoy spending time in the winter sun after hurricane season officially comes to an end on November 31st. One of the top things to do in Key West in December is to take a boat trip with a local company like Key West Sandbar Tours. You can spend your time on a sunset cruise and take in the breathtaking views while eating fresh lobster and seafood.

The boat tours provide you with the chance to learn more about Key West and enjoy a full-day trip on the water. You can play and frolic on the sandbars while having a great time with friends and family in a relaxing setting that will prove to be the highlight of your time spent in Key West in December. The beautiful weather will allow you to spend all of your time outside on the boat and in the sand while taking a dip in the water to cool off from the heat.

You can look forward to escaping to private tours while enjoying your time traveling on a luxurious boat. When you’re ready to have the experience of a lifetime, contact us at Key West Sandbar Tours to book a private charter and spend more time on the water!

Key West Boat Trips Are Perfect For Holiday Cheer


3 to 4 hours
Group Size
Up to 12

Sandbar Tour For Large Groups

If your group is larger than 6 and you have a hard time finding a boat ride to the sandbars because of the 6 passengers limit, we are here to help. You can book our 2 identical Hurricane 27 foot deck boats and our captains will drive them side by side so you can take cool photos and they will raft up the boats on the sandbars so you can enjoy and share this amazing time together.

3 to 4 hours
Group Size
Up to 6

Hopping Sandbars In Key West

What a perfect day to take a boat ride! You will see not one but several different sandbars on this tour! It will only take 25 minutes to get there on our epic adventure, and we can stop as long as you want at those sandbars that interest you the most. This is something you cannot miss!

Experience the mangrove trails of Mud Keys and hang out with locals at Snipe Point after. You won't want the day to end.

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2 hours
Group Size
Up to 6

Key West Sunset Cruise

Ocean, meet our captain! One of the best things about the backcountry waters is how it’s never too crowded. So jump in and enjoy the peacefulness and remoteness as you stand in the "middle of the ocean" with nothing but water around you. Optionally, bring some champagne to enjoy with the sunset as a backdrop. Then, just sit back and relax as you cruise on out into the middle of nowhere, leaving behind any stress or worries.

2 hours
Group Size
Up to 6

Mud Key Mangrove Safari

It's time for some adventure and excitement with a boat trip through the backcountry. After only a short ride, we'll take you on a leisurely cruise down to Mud Key Sanctuary, where you can enjoy the countryside and take in all the wonders of nature that surround you. Stop by the sandbar for a refreshing dip or just stroll around and soak up the sun. Capture your memories and cherish them forever.