Head to Key West for a Nautical Holiday Steeped in Sand, Sun and Surf

Key West Christmas

We may earn money or products from the companies mentioned in this post. At no extra cost to you, I only recommend products I have experience with. As an Amazon Associate, I earn from qualifying purchases.

In honor of sharing more ways to spend the holidays in Florida, I’m highlighting an article sent to me by Historic Tours, written by Kara Pound. This time we’re heading to the ultimate island vacation getaway, Key West.

At the tip of Florida and just 90 miles north of Cuba is Key West, a tropical island famous for its laid-back lifestyle, beautiful blue water, relaxing beaches and romantic appeal. While Key West is a great place to visit year-round, these islanders take the holidays seriously – transforming the seascape into a wonderland of twinkling lights, trolley tours, boat parades and live music events.

Key West is an island in the Straits of Florida and at the southernmost tip of the Florida Keys. With a total landmass of 4.2 square miles and an average yearly temperature of 77 degrees, it’s easy to see why popular local landmarks like Duval Street, Hemingway House, Key West Lighthouse, Mallory Square and Mile Marker 0 have been welcoming visitors for centuries. Add Key West to your upcoming holiday travel list and create memories to last a lifetime.

There are many reasons to spend the holidays in Key West. Here are a few of the most popular events and things to do.

Harbor Walk of Lights – Honoring Key West’s maritime history, the annual Harbor Walk of Lights kicks off the holiday season on Wednesday, November 22 as you walk along the seawall past Green Street, William Street and Margaret Street to the Key West Ferry Terminal. This free event, which stretches through New Year’s Eve, is fun for the entire family and features nautical theme light displays, shopping, dining and seasonal libations. Learn more here.

Holiday Lights and Sights Trolley Tour – One of the best ways to experience Key West during the holidays is aboard Old Town Trolley’s Holiday Lights and Sights Tour. While there won’t be a white Christmas in Key West, that doesn’t stop the island from decking the halls with lights and decorations. This 60-minute trolley tour begins in Mallory Square and includes cider and cookies before departure. Tours are offered Friday, December 8-9 at 6 pm, 7 pm and 8 pm as well as December 15-16 and December 19-23 at 6 pm, 6:15 pm, 6:30 pm, 7:15 pm, 7:30 pm and 7:45 pm. Tickets are $15 for adults, $7 for children ages 4 to 12 and children ages 3 and under ride free. Learn more here. 

Lighted Boat Parade – Twinkling lights illuminate the waters at Key West’s Historic Seaport for the 27th annual Schooner Wharf Bar & Galley Lighted Boat Parade. Dozens of boats parade through the waters starting at 8 pm on Saturday, December 9, but come early to catch the children’s House of Pan Steel Drum Band of Bahama Village as they perform on the Schooner Wharf stage from 6 pm to 8 pm followed by more live music by Raven Cooper and Friends. Learn more here.

There are many reasons to spend the holidays in Key West. Here are a few of the most popular events and things to do.

Fury Water Adventures – A staple for outdoor activities in Key West for almost 30 years, the largest watersports company in South Florida hosts a variety of holiday-themed events during November and December. Offering special trips on Thanksgiving, Christmas, and New Year’s Eve as well as a unique Lighted Boat Parade viewing experience that is second to none. Check out their special events calendar for all the details.

Support Small Businesses – Key West has hundreds of small, locally owned shops with one-of-a-kind items for everyone on your nice list. Art galleries dot the seascape featuring local artists creating everything from glass jewelry to handmade pottery and dozens of clothing boutiques and gift shops offer up everything from hammocks and seashells to vintage beach photos and eco-friendly treasures. Make sure to add popular destinations like Clinton Square Market and Mallory Square Marketplace to your shopping itinerary.

Rest & Relaxation – Inspiring guests like Ernest Hemingway and Tennessee Williams since it opened in 1926, La Concha Hotel & Spa is a National Historic Landmark in the heart of the vibrant downtown historic district. Located on Duval Street, the hotel was designed with comfort in mind and features contemporary accommodations with colorful ceilings, dark wood plantation furnishings, and coastally inspired window shutters. Enjoy a cocktail by the pool, dine at 430 Duval, sip world-class wines at Wine-O or stop by La Concha’s full-service spa for signature treatments at their rooftop facilities. Learn more here. 

Historic Lodging – There is no shortage of beautiful inns, hotels and bed and breakfasts dotting the landscape of Key West’s downtown. Built in 1898, Key West Bed and Breakfast is located in the William Russell House and is listed on the National Register of Historic Places. Constructed by Bahamian shipbuilders, this three-story Victoria is located on a quiet, tree-shaded street in the heart of Old Town. With a short walk to the water and Caribbean-style guest rooms, you’ll find it easy to rest and relax at Key West Bed and Breakfast. Learn more here. 

There are many reasons to spend the holidays in Key West. Here are a few of the most popular events and things to do.

Read more on how to do the Holidays in Florida, specifically St. Augustine and Tampa.

Leave a Comment

Your email address will not be published. Required fields are marked *

This site uses Akismet to reduce spam. Learn how your comment data is processed.

Scroll to Top