Why You Won’t Regret A Visit To Key West in the Winter

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Disclosure:  Hotels.com asked me to share my ideas on what to do in Key West in the winter.

If you do decide to travel at this time, we suggest that you take the following precautions: wear a face mask; bring hand sanitizer and wash your hands on a regular basis; check official websites for the latest updates; and book a hotel with free cancellation in case your plans need to change.

It’s amazing how a warm weather destination like Florida even for just a few days can chase away the winter blues and leave you energised until the return of spring. Thanks to the tropical weather, white-sand beaches, and an abundance of festive holiday events, Key West in the winter is one of the best places in Florida for a relaxing winter sun break. Here’s why you should consider enjoying a Key West winter by visiting Key West at Christmas for family-friendly fun. Throughout the month Christmas festivities are happening in Key West in December. Alternatively, visit Key West in January where you can ring in the new year with a raucous Key West New Year’s Eve. While we were visiting Key West for Christmas, we met one lucky family from Ireland who were staying at our resort for most of December and January.

Key West In Winter

Compared to other places in the United States, a Key West winter sees particularly warm weather. Although temperatures tend to be slightly lower than the summer months, it’s still the perfect weather for sightseeing, water sports, and even sunbathing.

Christmas decor on a house in Key West florida
Key West for Christmas brings out its holiday finery to celebrate the holiday season!

There is very little rain in Key West in the winter, which is ideal for travelers interested in spending the majority of their vacation outdoors. Despite what you may think from that classic movie, Key Largo (1948) with Humhrey Bogart and Lauren Bacall, December is also the start of the dry season in the Florida Keys and hurricane activity is low.

Key West in December

In Key West in December, the average daily temperatures hover around the mid to high 7os. The average lows in Key West in December tend to be in the mid-60’s as well. You can expect the average Key West temp in December to be perfect for outdoor activities.

Key West in January

In Key West in January the average daily temperature is in the mid 70s with average lows never dropping  below the mid 60’s.  It’s Caribbean weather really which makes sense considering Cuba lies only about 90 miles from Key West.

Southernmost Point marker, Key West, Florida, USA
No wonder Key West in January has balmy weather considering it’s so close to the Caribbean islands.

Sunny days and warm weather is what makes Key West in winter so special. Yet, it’s the Caribbean flavour without the need to get on a plane or use a different currency that keeps the visitors returning every winter to Key West.

Where To Stay in Key West with Kids

As a popular tourist destination, Key West Florida has a wide range of accommodation options. Lodging in Key West includes hotels, resorts and bed and breakfasts. As family travellers, we looked for where to stay in Key West with kids that had pool options. My kids are all about the pool(s) wherever they stay.

We are fans of the Hyatt Centric Key West Resort and Spa for its amenities and excellent location. Only a short distance to Mallory Square, we could watch the sunset celebration and the performers that would come out every evening. Note that Hyatt has several other options for Hyatt Residence Club members such as Hyatt Windward Pointe.

colorful cottages in Key West Florida
Key West in December has all the bright colors and warm weather of a vacation in the Caribbean without actually having to fly to the Caribbean

Casa Marina Resort (part of the Waldorf Astoria hotel chain) is also another good place to stay in Key West with kids because it has multiple pools and a private beach.

A more budget-friendly yet family-friendly option would be one of the two Marriott’s Fairfield Inn and Suites in Key West.

Near Key West, we have also stayed at the Hawks Cay Resort which is very family-friendly. You can stay at the hotel or rent a villa. We stayed at the hotel but the villa rental would have been better value. It’s on the island of Hawks Cay though and about a 1.5 hour drive away from Key West itself.

Key West at Christmas

If you’re looking for a unique way to spend your Christmas, look no further than beautiful Key West in December. Despite the warm temperatures, Key West for Christmas is one of the best places to feel that festive holiday cheer throughout the whole month of December.

Kick-off the holiday season with the Lighting of the Key West Harbor Walk of Lights. In late November, visitors and locals gather at the Harbor Walk to see the official lighting of the Fishing Buoy Tree marking the start of Christmas in Key West!

Residents of Key West also love to decorate their homes with Christmas lights. You can sign up for a Holiday Lights & Sights Tour with the Old Town Trolley to see all the brightly lit homes on the island (while cruising around in a light-up old fashioned trolley!). The Conch Tour Train Holiday Lights Tour is another classic tour option to see the lights around town.

Conch Train in Key West Florida
A Conch Train tour is a fun way to explore Key West with kids.

It’s not only homes that are decorated in Key West at Christmas. Stop by the historic seaport for the Annual Lighted Boat Parade which is a parade full of decorated sailboats, catamarans, and motorboats. You can watch the parade from the Key West Bight, or take part in the action by sailing on the Fury Catamaran parade tour.

The annual Key West Holiday Parade is a family-friendly event in Key West in December. This parade sees dozens of parade floats, marching bands, civic leaders, and local groups winding their way through the streets of downtown Key West. Of course, the parade ends at Eaton St with a special appearance by Santa Claus and Mrs. Claus on a decorated float!

NB!  AlthoughKey West has a reputation as a party place, Key West is also very family-friendly. During the day even crazy Duval Street is quiet and kid-friendly. There’s plenty for kids to do in Key West such as visit the cats at Hemingway’s House, check out Truman’s Little White House, or visit the Shipwreck Museum.

Key West New Year’s Eve

From glamorous dinners to once-in-a-lifetime parties, a Key West New Year’s Eve can ring in your new year in a special way.

Start the day with the annual Key West Dachshund Walk. This parade features hundreds of adorable dachshunds dressed up in cute costumes, festive attire, and sometimes outrageous get-up.

Partygoers are spoiled for choice when it comes to New Year’s Eve events. One of the night’s biggest events is the Conch Shell Drop at Sloppy Joe’s Bar on the corner of Greene and Duval Streets. This loud and boisterous event is guaranteed to be one of your favourite Key West New Year’s Eve memories

A Key West New Year’s wouldn’t be complete without paying homage to the city’s maritime heritage. The Schooner Wharf near the waterfront hosts a pirate-themed New Year’s Eve celebration; a pirate wench is dropped from the top of a bar with the sounds of cannons blasting in the background.

Lobster traps making up a Christmas tree in Key West Florida
Christmas in Key West marked with a lobster trap tree!

However, the most unique New Year’s event in Key West takes place at the Bourbon Street Pub. Once the clock strikes midnight, a local drag queen gets lowered from the pub’s balcony riding a giant high-heeled stiletto, with thousands of partygoers cheering around her. This event is televised worldwide and is one of the most beloved traditions in Key West for over 20 years.

Of course, there are dozens of other low-key events happening around Key West. Upscale dining experiences, champagne bashes, and live musical performances are all great alternatives to the lively and sometimes rowdy New Year’s Eve parties.

And, remember Key West being what it is, the party continues in Key West in January and beyond.

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Pinterest image with colorful cottages in Key West Florida with the text: “How To Spend New Year’s in Key West Florida"
Looking for ways to spend New Years in Key West? Key West Florida in December and January has great weather and a festive holiday feel. Check out our selection of things to do in Key West (incuding Key West for families) – one of our picks will ensure you usher in the New Year in style. New Years Eve in Key West can be as crazy or as low-key as you want it to be – either way you are guaranteed to love Key West in winter. It’s the travel aesthetic of the Caribbean without leaving the USA!

This article has been done in collaboration with Hotels.com. We have self-funded our travel to Key West, including any hotels mentioned herein. 

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