Flip-Flops, Boat Parades, and Santa in Shades: It’s a Keys Christmas!

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🌴 Trading Snowflakes for Seabreeze

I used to think Christmas had to smell like pine and sound like Bing Crosby on loop. Then I spent one December in the Florida Keys. Now? Give me sunburned Santas, boat parades, and enough Key lime pie to make a reindeer blush.

This week, I’m sharing what’s still on the calendar — because while most folks are scraping ice off windshields, you could be watching a lobster trap Christmas tree light up a marina.

So here’s how to unwrap the best of the Keys between now and the big day…

Key West: Holiday Hijinks in Flip-Flops

I arrived in Key West expecting quirky. I got full-blown Christmas fever, island-style.

🛥️ Lighted Boat Parade – Dec 13
Forget reindeer — in Key West, Santa sails. Picture schooners decked out in LED lights, snowmen on paddleboards, and the kind of crowd that cheers with conch shells. Best watched with a drink from Schooner Wharf Bar in hand. Bonus points if it’s got a candy cane garnish.

☕ Cocoa & Carols Cruise – Dec 19–24
Board the Schooner America 2.0 for an evening cruise where carolers sing, cocoa flows, and the sun dips behind Mallory Square like it's on cue. It’s part Hallmark movie, part Jimmy Buffett soundtrack.

🚗 Holiday Classic Car Show – Dec 21
It’s not Christmas in the Keys until someone decorates a vintage Mustang with tinsel and a blow-up flamingo. That’s the vibe at the annual car show in the Conch Republic Seafood Co. parking lot.

Marathon: Christmas, Easy-Breezy

Some places do the holidays loud. Marathon does it laid-back, like a hammock under a palm tree.

🛳️ Key Colony Beach Boat Parade – Dec 14
Small boats, big lights. The kind of neighborhood parade that makes you feel like a local even if you rolled in from I‑95 that morning.

🌲 Crane Point Winter Wonderland – All Month
Snow machines. Santa in shades. Tropical trees wrapped in lights. It’s the only time I’ve ever seen a heron and a snowflake in the same photo. Bring the kids — or just the kid in you.

🍹 Upper Keys Cheer: Islamorada & Key Largo

The Upper Keys might be quieter, but they know how to throw a party — especially when boats and twinkle lights are involved.

🛥️ Key Largo Lighted Boat Parade – Dec 13
Find your spot at Sundowners or Caribbean Club, grab something grilled, and enjoy another round of floating holiday magic. More mellow than Key West, but just as sparkly.

Only-in-the-Keys Christmas

🎄 Dive the Christmas Tree Cave
At French Reef, there’s a coral cave crawling with Christmas tree worms — yes, real animals, not decorations. They puff up like tiny party favors when you swim by. It’s a holiday dive that’s more “Finding Nemo” than Frosty the Snowman.

🍾 Christmas Morning Brunch Sail – Dec 25
No ovens. No in-laws. Just a boat, bottomless mimosas, and salty air. I boarded thinking I’d miss home. I disembarked wondering how to make this a yearly tradition.

🧳 Before You Go

• Weather forecast? High 70s, light breeze, zero chance of snow.

• Crowd level? Rising. Book now if you want that front-row seat or waterfront table.

• Packing tip? Leave the sweater. Bring the SPF 50 and something with flamingos on it.

🎁 Final Word from the Road
Christmas in the Keys doesn’t just feel different — it is different. It’s about joy without the stress, light shows on the water, and new traditions you never saw coming.

From me to you: Merry Keys‑mas. May your days be merry and sun-drenched.
– Your road trip guide, weathered by salt but warmed by rum,

🐚 — FloridaKeysRoadTrip.com

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