Celebrate the Magic of the Florida Keys: A Guide to the Week Between Holidays 🌴🎉

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Dear Road Trippers,

As the year winds down, the Florida Keys come alive with festive energy and unique events that make the week between Christmas and New Year’s truly unforgettable. Whether you’re here to relax after the holiday hustle or dive headfirst into island adventures, there’s no better place to celebrate the season.

Here’s our guide to the best activities, events, and experiences to close out the year Florida Keys-style!

1. Stroll Through the Holiday Lights

The islands are still glowing with festive cheer! Be sure to check out these magical displays:

• Harbor Walk of Lights (Key West): Wander through the Key West Historic Seaport to see the famous lobster trap tree, buoy tree, and sparkling light displays.

• Holiday Boat Parade Winners (Marathon): The decorated boats from Marathon’s annual parade are often docked and lit up for viewing throughout the week.

• Key Largo Holiday Light Display: Stop by local marinas and neighborhoods to soak up the island's unique twist on holiday decor.

2. Countdown to the New Year with Unique Keys Traditions

Why settle for a traditional ball drop when you’re in the Keys? Here are some of the most anticipated New Year's Eve events:

Conch Shell Drop at Sloppy Joe’s Bar
Join the lively crowd on Duval Street for the annual "Conch Shell Drop," where a massive manmade conch shell descends to mark the New Year. The event features a rooftop host, dancing in the street, and a countdown displayed on a huge clock.

Red Shoe Drop at Bourbon Street Pub
Experience the famous "Red Shoe Drop" at the Bourbon Street Pub/New Orleans House, where local drag queen Sushi is lowered in a giant red high-heeled shoe. The streetside show begins at 9 p.m., featuring local and national performers, with the drop at midnight. The event is free, with VIP balcony viewing available for purchase.

Pirate Wench Drop at Schooner Wharf Bar
Celebrate at Schooner Wharf Bar with the "Lowering of the Pirate Wench" from the mast of the Schooner America 2.0. The party starts early with live music from local and national acts, party favors, and champagne. The wench is lowered at midnight, accompanied by cannon fire and a festive crowd.

Gatsby Gala and 'Plane Drop' at First Flight Island Restaurant & Brewery
Dress in your finest Gatsby-era attire and attend the New Year's Eve Gatsby Gala at First Flight Island Restaurant & Brewery. Enjoy live music, DJ tunes, heavy hors d'oeuvres, chef-manned food stations, and an open bar. At midnight, witness the "Plane Drop," where a replica of an old Pan American plane with a real-life stewardess takes flight in the garden.

Cuban Cigar Drop at El Meson de Pepe
For a unique twist, head to El Meson de Pepe in Mallory Square for their "Cuban Cigar Drop." Enjoy authentic Cuban fare and a lively atmosphere as you welcome the New Year with this distinctive celebration.

Pro Tips:

• Arrive Early: These events are wildly popular, so plan to arrive early to secure a good spot.

• Transportation: Consider using local transportation or walking, as parking can be challenging during these events.

• Dress Accordingly: While the Keys boast warm weather, evenings can be breezy. Dress comfortably and consider bringing a light jacket.

• Stay Hydrated: With all the excitement, it's easy to forget to drink water. Stay hydrated, especially if you're enjoying alcoholic beverages.

• Respect Local Regulations: Be aware of and adhere to any local guidelines or restrictions in place during the festivities.

3. Explore the Great Outdoors

After the holiday feasts, soak up some sun and take in the natural beauty of the Keys:

• Kayak Through Mangroves: Take a guided tour in Islamorada or Big Pine Key and explore the quiet, serene waterways.

• Visit Dry Tortugas National Park: Hop on the ferry from Key West for a day of snorkeling, history, and pristine beaches.

• Relax on Sombrero Beach: One of the most family-friendly beaches in Marathon, perfect for picnics or a casual beach day.

4. Don’t Miss the Local Festivities

The week between holidays is filled with fun local events:

• The Sunset Celebration (Mallory Square, Key West): Join street performers, artisans, and musicians to watch the final sunsets of the year.

• Live Music at Green Parrot Bar (Key West): Dance the night away with live performances at this legendary Key West venue.

• Florida Keys Craft Beer (Islamorada): Sample some of the best local brews while enjoying live music and island vibes.

5. Toast the New Year with Island Drinks

Ring in the New Year with these tropical cocktails:

• Rum Runner: A fruity mix of rum, banana liqueur, and blackberry brandy—a Keys classic.

• Key Lime Mojito: A refreshing twist on the traditional mojito with the zing of Key lime juice.

• Coconut Espresso Martini: Perfect for those who need a caffeine boost to dance till midnight!

Check out local bars like The Green Turtle Inn (Islamorada) or The Rum Bar (Key West) for specialty drinks. Also, make sure to visit our friends at Mixologist Master for innovative recipes to these famous drinks.

Plan Ahead for 2025

The Florida Keys are packed with amazing events to kick off the new year! Stay tuned for next week’s newsletter, where we highlight the best January festivals, top outdoor activities, and hidden gems to help you plan your next unforgettable road trip through the Florida Keys.

Have a favorite Florida Keys holiday memory? Reply to this email and share your story—we’d love to feature it in an upcoming edition!

Wishing you sandy toes, salty breezes, and a joyful New Year,
Brian

Florida Keys Road Trip Team