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Christmas in Key West: A Tropical Holiday Road Trip From Miami

When most people think “Christmas,” they picture snowmen, iced-over windshields, and shoveling the driveway at sunrise. But down here? Nah. In South Florida we do Christmas with warm breezes, turquoise water, and palm trees wrapped in twinkling lights — and honestly, that’s the way Santa should’ve been doing it all along.

If you start your adventure in a shiny Mustang convertible or a Jeep Wrangler from Miami Convertibles Car Rental, the whole holiday vibe kicks up another level. Picture cruising US-1 with the top down, holiday playlists blasting, sun on your shoulders, and the Keys opening up like the world’s most festive postcard.

And once you roll into Key West? Whew. The island goes all in on Christmas.

Let’s dive into the best events, lights, and holiday magic waiting for you at the southernmost tip of the U.S.



🌟 Harbor Walk of Lights: Christmas by the Water

Down at the Historic Seaport, the Harbor Walk of Lights glows every night through the holidays — think thousands of lights reflected on the water, giant nautical trees made of lobster traps, and whole docks transformed into tropical Christmas wonderlands.

It’s the perfect spot to stretch your legs after the drive from Miami, grab a café con leche, and watch the sky turn pink before the lights flick on. Trust me, your convertible will look phenomenal parked nearby under the glow.


🚤 Schooner Wharf Lighted Boat Parade

December 13, 2025

This one is pure magic: dozens of boats — kayaks, yachts, sailboats — cruising through the seaport dressed to the nines in Christmas lights. It’s Key West’s version of a sleigh parade, just… saltier.

Locals line the docks, music everywhere, drinks flowing, and that warm holiday buzz in the air. If you’ve never seen a boat shaped like a giant glowing dolphin, this is your chance.


🎉 Hometown Holiday Parade

Key West knows how to throw a parade — it’s festive, tropical, quirky, and family-friendly. Floats roll down Truman and Duval with Caribbean colors, marching bands, tropical Santa hats, and all the island charm you expect.

If you’ve brought the family along for the Mustang Christmas adventure, they’ll love this one.


🚴 The BeLighted Bike Ride

Only in Key West will you find hundreds of people cruising around on bicycles covered in lights. Flamingos, dolphins, palm trees — every bike is a piece of holiday art. It feels like a moving Wynwood mural with Christmas spirit.


🚂 Holiday Lights Tours

Hop on the Old Town Trolley or Conch Train if you want a relaxing way to take in all the decorated homes. Key West locals go all-out — imagine Victorian houses with rainbow lights, giant inflatable flamingos wearing Santa hats, and yards full of tropical Christmas displays.

Perfect for a chill night after a long day exploring.


⛵ Cocoa & Carols Sails + Christmas Day Brunch Cruise

Key West never misses a chance to celebrate on the water. During December, you can jump on a Cocoa & Carols sunset sail — hot cocoa, holiday cookies, live music, and nothing but glowing harbor views.

On Christmas morning, the brunch cruise is a whole vibe: mimosas, sun-drenched decks, and views that beat any snow globe.


🎁 Key West Car Show & Toy Drive

For the car lovers (aka, our people), the annual holiday car show brings vintage rides, classics, Jeeps, Mustangs — everything decked out with tinsel and lights. Plus, it supports local toy drives, so you get your car fix and give back.


🎅 Why a Christmas Road Trip to Key West Just Hits Different

Here’s what makes Christmas in Key West so special — especially when you roll down from Miami in a Mustang convertible:

  • No snow, no stress — just sunshine, salt air, and that Keys freedom.

  • Holiday lights reflecting on water instead of ice.

  • Boats instead of reindeer.

  • Santa in board shorts.

  • And that US-1 road trip? Pure cinematic magic with the top down.

If you’re spending the holidays in South Florida or looking for a warm getaway, Key West is the perfect blend of festive and tropical. And honestly, the drive alone is worth it — there’s nothing like cruising the Seven Mile Bridge with Christmas music playing and island breezes flying through the cabin.


🚗 Start Your Holiday Road Trip With Miami Convertibles Car Rental

Whether you're grabbing a Mustang GT to feel like the star of your own Christmas movie, or a Jeep Wrangler for that open-air island vibe, we’ve got your perfect holiday ride.

Let’s make this Christmas the kind you’ll actually brag about.

📞 Contact Us — Let's Get You in the Driver’s Seat!

📱 Phone: (305) 799-7892

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🚗 Book Now: Reserve Your Convertible

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❓ Frequently Asked Questions About Christmas in Key West


1. Is Christmas a good time to visit Key West?

Absolutely — it’s one of the best times of the year. The weather is warm, the island is buzzing with holiday events, and the whole place lights up with tropical Christmas charm. Think sunny days, breezy nights, and zero chance of snow ruining your plans.


2. What are the top Christmas events in Key West?

The biggest hits are the Harbor Walk of Lights, the Schooner Wharf Lighted Boat Parade, the Hometown Holiday Parade, the BeLighted Bike Ride, and the festive Holiday Lights Trolley & Train Tours. There’s also a Cocoa & Carols Sail, Christmas brunch cruises, and even a holiday car show and toy drive.


3. How long is the drive from Miami to Key West?

Plan for about 3.5 to 4.5 hours, depending on traffic. But honestly? With the top down on a Mustang or Jeep from Miami Convertibles Car Rental, the drive becomes part of the magic. The Seven Mile Bridge, turquoise water on both sides… it’s a Christmas road trip you’ll remember forever.


4. Do I need to book holiday activities in advance?

For popular events like the Lighted Boat Parade, holiday sails, and Christmas brunch cruises, it’s a good idea to book early. Key West fills up fast in December — tropical Christmas is a hot commodity!


5. What should I bring for a Christmas trip to Key West?

Pack light, breathable clothes, comfy shoes, a Santa hat for photos, and sunscreen (trust me, Christmas sun is still real sun). If you’re renting a convertible, bring your playlist and sunglasses — the holiday breeze on US-1 is unbeatable.

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