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11/15/2024

Sun-Kissed Holidays: Your Ultimate Guide to Planning Winter Break and Christmas in Key West

Are you dreaming of trading in your snow boots for flip-flops this holiday season? Well, pack your Santa hat and sunscreen, because we're about to sleigh ride straight into paradise! Key West is calling, and it's time to answer with a jolly "Ho-Ho-Whoa!"

Picture this: while the rest of the world is shivering, you're sipping a frosty margarita on a sun-drenched beach, watching palm trees sway to the rhythm of "Jingle Bells." It's not a mirage, folks – it's just another day in our little slice of tropical heaven. So why not make your winter wonderland a little more wonderful (and a lot less winter) this year?

Holly Jolly Happenings, Traditions and Events

Let's dive into the holly jolly happenings that'll make all your Key West celebrations unforgettable:

  • Key West Holiday Parade

Imagine Santa trading his sleigh for a surfboard! Our early December parade is like Christmas and Mardi Gras had a baby – complete with twinkling floats, merry marching bands, and ol' St. Nick sporting his best Hawaiian shirt.

  • Lighting of the Harbor Walk of Lights

Who needs the Northern Lights when you've got the Harbor Walk of Lights? This dazzling display turns our Historic Seaport into a twinkling tropical fairyland. It's like someone sprinkled pixie dust all over the palm trees!

Join the Chabad of Key West for their annual Hannukah celebration. Witness the lighting of the Menorah ceremony and enjoy live music, dreidels, gelt, and donuts! 

Take a stroll through our decorated seaport, where the only thing more intoxicating than the holiday cheer is the rum in your eggnog. With festive tunes and mouthwatering treats, it's a feast for all your senses!

  • Historic Inn Tours

Mid-December brings a chance to peek into Key West's swankiest digs, all dolled up for the holidays. It's like MTV Cribs meets Miracle on 34th Street – with a dash of pirate treasure for good measure. Take the trolley to add nostalgia!

  • Holiday Concerts and Performances 

From the Key West Theater to St. Paul's Episcopal Church, our island is alive with the sound of music (and maybe a little off-key caroling after a few too many cocktails).

Our boats dress up fancier than a debutante at a Christmas ball. Watch these floating works of art light up the night as they cruise through Key West Bight and the Historic Seaport.

The historic home is decked out prettier than a Christmas tree. Even Papa's cats get into the holiday spirit, making it the purr-fect spot for some festive feline fun.

  • New Year's Eve Celebrations

Where else can you watch a giant conch shell, a drag queen in a red shoe, and a pirate wench all "drop" at midnight? Only in Key West, baby! It's the perfect way to say "see ya later" to the old year and "well, hello there" to the new one.

Now, imagine experiencing all this magic from the comfort of your own luxury beach house. No fighting for parking, no trudging through snow – just step out onto your private slice of paradise whenever the holiday spirit moves you. Wake up to the sound of waves instead of alarm clocks, and trade in your ugly Christmas sweater for festive holiday swimwear.

Key West Makes The Holidays Fun for Everyone

In our tropical paradise, there's room for everyone under the palm trees!  We're all about spreading the joy as wide as the ocean, no matter what you're celebrating.  Imagine Hanukkah menorahs glowing alongside twinkling palm trees, Kwanzaa candles casting a warm light on the sand, or even a Festivus-inspired "airing of grievances," so long as it’s island style – where the only complaint is that your glass is empty?

Remember, in our little slice of paradise, we're not just decking the halls – we're decking the beaches, the boats, and anything else that doesn't move fast enough! So whether you're spinning a dreidel, lighting a kinara, or leaving cookies for Santa, there's a spot for you on our sun-soaked shores.

Let's keep that laid-back, "no worries" vibe flowing like a gentle tide. After all, the beauty of our Key West getaway is that it's a melting pot of cultures, traditions, and holiday cheer – all served up with a little paper umbrella, of course!

There’s always fun to find in Key West

In Key West, you can hop on a holiday sunset cruise and toast to the most colorful sky you've ever seen. Kayak through mangroves dressed up in their holiday best, or take a culinary tour that'll make your taste buds think they've died and gone to flavor heaven.

So, what are you waiting for? Ditch the winter blues and come paint the town red (and green) with us at Margaritaville Beach House Key West. After all, in Margaritaville, every day is a holiday.

Happy Holidays, folks – in sun-kissed Key West style! 

Ready to reserve? Book your trip today.

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