The Sunny Escape You're Dreaming of This Holiday Season | Florida Keys

Can’t stop fantasizing about mellow beach days during the cold holiday season? Seeking a cozy and relaxing-friendly destination? If you're all about sensational sunsets, unforgettable places & exquisite food, the perfect place for you to visit while on vacation will be our favorite hidden gem in Florida, the one and only Key West! *Spoiler alert: This blog post includes a free travel plan.*

Let’s be honest – who doesn’t dream of sunny beaches when you’re stuck inside during the winter (if you're from the north, you’ll know exactly what we're talking about). If you haven't tasted the Key West lifestyle just yet, you’ll be excited to know that it prides itself on carefree balmy weather during the winter, and the chance of rain is also lowest this time of the year. 

Once you're here, this tropical island is full of surprises. Picture coral reefs (some of the most iconic coral reefs in the world), festivals for the entire family, restaurants, museums, ghost tours, one-of-a-kind sailing, kayaking, and snorkel and scuba diving experiences. Here are 5 of our favorite warm weather experiences in Key West in Winter. Turn off the heater, and let's dive in!

Relax At the Beach

If you’ve been googling the best beach getaways this time of year, you can’t miss Key West. It’s home to secluded beaches offering peace and serenity to visitors from all over the world. Sunbathing, reading, tanning, eating delicious seafood, and taking advantage of colorful sunsets from the comfort of your backyard, Key West might just be the ideal vacation. 
Smathers Beach is one of the best beaches in Key West! A famous public beach with plenty of open space to sunbathe or have a kick about. If you're looking for a beach spot that feels even more secluded, here's our top list of 5 hidden beaches through The Keys.

Enjoy Top-Rated Water Activities

Water activities in Key West are also a perfect way to get out and away from it all. Whether you prefer to kayak, jet ski, para-sail, or paddleboard, you'll have an opportunity to see marine life, aquatic birds, and tropical habitats. 

If you're looking for something more private & relaxing, Barefoot Billy can get you set up with everything from catamaran cruises to private charters around Key West. Take a look at our provider's list here.

Bike Through The Island Like a Local 

Biking is one of the best ways to get around the island! You can cover more ground on a bike than walking while still enjoying Key West's iconic architecture, attractions, tropical streets, and more. You can rent a bike or go on a bike tour with local companies. If you're riding on your own, follow the road rules to stay safe. Ask us about sweet deals on bike rentals.

If you’d rather experience Key West like a local, take a sneak peek at the non-touristy things to do while vacationing in the sun.

Spend Valentine's Day With Your Boo at Key West 

If you're looking for romantic activities to try with your significant other, Key West in February is perfect. The temperatures are warm, and there are plenty of things to do as a couple. 

From dinners overlooking stunning sunsets to exploring turquoise waters with your better half, the sky's the limit when it comes to romance in Key West. We've compiled a full day of cheesy things to do across the island with your boo.

Dive into Key West Holiday Events And Activities

Sip cider and indulge with holiday cookies at the Holiday Sights & Festive Nights; this list is another excellent way to get in the spirit of the holiday season:

  • Celebrate the Key West Holiday Season with tinsel & tunes at Truman Little White House.

  • Ride the Key West Historic Conch Tour Train, and enjoy the light display, cider & cookies. 

  • Be delighted by the Nutcracker ballet at Tennessee Williams Fine Arts Center.

  • Watch the panoramic views at the Lighted Boat Parade at Schooner Wharf. 

  • Be part of the Key West Holiday Parade the first week of December. 

  • Prepare for New Year’s at the Key West Eve Shoe Drop celebration on Duval Street.

We're putting together a broader snowbird itinerary just for you. Stay tuned for more info in our next blog post; in the meantime, subscribe to our monthly newsletter to keep you updated on the latest happenings through Key West. Subscribe below.

There’s no Place on Earth Quite Like Key West

While it may seem counterintuitive to head to a tropical locale to catch the holiday spirit, Key West during the Winter is a wonderland of festive surprises. While the weather gets milder from November through February, you'll still experience bright sunny days and refreshing ocean breezes. Fun activities and special winter events are not in short supply, that’s for sure. Locals and visitors from all over the world enjoy a bevy of merry events and attractions throughout the upcoming months.

There you have it, so if it is your first holiday season in Key West, be sure to reach out to us. We can offer everything from accommodation to must-see places. We can't wait to see you; book your free travel plan & ditch the cold this Winter.