Happy 2025! Let’s Kick Off the New Year in Florida Keys Style 🎉🌴

Dear Road Trippers,

Welcome to 2025! 🌟 We hope your New Year’s celebrations were as magical as a sunset over Mallory Square. Whether you joined the party in the Florida Keys or toasted from afar, there’s no better time to reflect on unforgettable moments and look ahead to the adventures this year will bring.

Let’s start with a quick look back at the New Year’s Eve highlights and then dive into something special to kick off the new year.

1. New Year’s Eve Highlights in the Florida Keys

Key West is famous for its unique and colorful take on New Year’s Eve celebrations, and the island pulled out all the stops for 2025. From glamorous events to quirky traditions, here’s a closer look at the iconic drops that lit up the Keys this year:

🎉 Conch Shell Drop at Sloppy Joe’s Bar

Location: 201 Duval Street, Key West, FL
Website: sloppyjoes.com

For more than two decades, Sloppy Joe’s Bar has hosted the Conch Shell Drop, a quintessential Key West tradition that rivals Times Square’s famous ball drop. As thousands of revelers gathered on Duval Street, the 6-foot pink conch shell began its glowing descent at the stroke of midnight, accompanied by fireworks and live music.

What makes this drop special is the electric energy of the crowd—locals and visitors alike singing, dancing, and toasting to the New Year. Street performers and vendors lined the area, adding to the festive atmosphere. Pro tip for next year: Arrive early to secure your spot near the main stage!

👠 Red Shoe Drop at Bourbon Street Pub

Location: 724 Duval Street, Key West, FL
Website: bourbonstpub.com

The Red Shoe Drop has become one of the most celebrated LGBTQ+ events in the Keys, bringing a fabulous flair to New Year’s Eve. This year, the glamorous drag queen Sushi descended from a super-sized red stiletto as the crowd below erupted in cheers.

The spectacle began long before midnight, with live performances and a countdown hosted by a cast of local and national talent. Confetti rained down as Sushi landed gracefully, waving to fans and giving her signature sass.

This event, held at the Bourbon Street Pub, is free to attend, but VIP balcony seating sells out fast. Be sure to snag a ticket next year for an exclusive view of the drop!

🏴‍☠️ Pirate Wench Drop at Schooner Wharf Bar

Location: 202 William Street, Key West, FL
Website: schoonerwharf.com

Over at the historic Key West Seaport, the Pirate Wench Drop is a crowd favorite for those who prefer a swashbuckling celebration. At Schooner Wharf Bar, the pirate wench was lowered from the mast of the majestic Schooner America 2.0, surrounded by cannon fire, cheers, and the sounds of live music.

The party kicked off early with a lively atmosphere that included costumed pirates, flowing drinks, and plenty of party favors. As the wench descended, the crowd joined in singing sea shanties to ring in the New Year. This event has a family-friendly vibe earlier in the evening but transforms into a spirited adult celebration as midnight approaches.

🎩 Gatsby Gala and Plane Drop at First Flight Island Restaurant & Brewery

Location: 301 Whitehead Street, Key West, FL
Website: firstflightkw.com

The Gatsby Gala at First Flight Island Restaurant & Brewery transported attendees to the roaring 1920s with its elegant décor and live jazz music. Guests donned their finest Gatsby-inspired attire, enjoying champagne towers, chef-curated hors d'oeuvres, and a gourmet dining experience.

The highlight of the evening came at midnight with the Plane Drop. Paying homage to the building’s history as the birthplace of Pan American Airways, a vintage replica plane was "dropped" in the garden courtyard, complete with dazzling lights and cheers from the crowd. The garden’s lush tropical ambiance made it the perfect spot to toast to 2025 in style.

The Spirit of the Keys on New Year’s Eve

Each of these events captures the unique and diverse culture of the Keys, offering something for everyone—from lively street parties to sophisticated soirées. If you missed this year’s celebrations, start planning for next year—it’s never too early to join in the magic of ringing in the New Year in paradise!

2. January Sneak Peek: A Road Trip Through Island Flavors

This January, we’re diving into the rich culinary scene of the Florida Keys with a focus on hidden gems and iconic eats. Whether you’re a foodie on the hunt for fresh seafood or a traveler craving the Keys’ signature flavors, these stops are must-visits:

🍋 Key Lime Pie at Blue Heaven (Key West)

Location: 729 Thomas St, Key West, FL 33040
Website: blueheavenkw.com

Blue Heaven’s Key Lime Pie is legendary, with a towering meringue that defies gravity and a filling that strikes the perfect balance between tangy and sweet. Enjoy this iconic dessert in their colorful courtyard, surrounded by roosters and lush tropical foliage.

🍤 Conch Fritters at The Green Turtle Inn (Islamorada)

Location: 81219 Overseas Hwy, Islamorada, FL 33036
Website: greenturtleinn.com

A true Islamorada institution since the 1940s, The Green Turtle Inn is famous for its conch fritters—crispy on the outside, tender and flavorful on the inside, and paired with a tangy dipping sauce. The menu also features creative seafood dishes and a welcoming, retro vibe.

🦞 Lobster Reuben at Keys Fisheries (Marathon)

Location: 3502 Gulfview Ave, Marathon, FL 33050
Website: keysfisheries.com

This is not your average Reuben sandwich! The Lobster Reuben at Keys Fisheries replaces corned beef with fresh, juicy lobster, layered with Swiss cheese, sauerkraut, and Thousand Island dressing on rye bread. Grab a seat by the water and savor this unique twist on a deli classic.

🐠 Hogfish Sandwich at Hogfish Bar & Grill (Stock Island)

Location: 6810 Front St, Stock Island, FL 33040
Website: hogfishbar.com

Tucked away on Stock Island, this casual eatery is beloved for its Hogfish Sandwich—lightly grilled and served with onions, Swiss cheese, and mushrooms on fresh Cuban bread. Pair it with a cold beer and enjoy the rustic dockside atmosphere.

🍤 Shrimp Tacos at Garbo’s Grill (Key West)

Location: 409 Caroline St, Key West, FL 33040
Website: garbosgrillkw.com

This food truck is a local favorite for its inventive shrimp tacos, made with fresh, perfectly seasoned shrimp, cilantro, and creamy aioli. Enjoy your meal with a cold craft beer from the bar next door at Hank’s Hair of the Dog Saloon.

Sip Your Way Through the Keys

No Florida Keys culinary adventure is complete without indulging in a few signature drinks:

🍹 Rum Runners at Islamorada Brewery & Distillery

Location: 82229 Overseas Hwy, Islamorada, FL 33036
Website: islamoradabreweryanddistillery.com

Kick back with a classic Rum Runner at this local favorite spot, where craft cocktails are made with their in-house rums and spirits. The brewery also features a rotating selection of craft beers.

🍸 Key Lime Mojito at The Rum Bar (Key West)

Location: 1117 Duval St, Key West, FL 33040
Website: rumbarkeywest.com

This refreshing mojito combines the zesty tang of Key lime with the minty kick of a traditional mojito. The cozy Rum Bar is located inside the historic Speakeasy Inn and offers an extensive selection of fine rums.

These culinary stops offer a delicious way to kick off the New Year. Stay tuned for next week’s newsletter, where we’ll share even more insider tips for exploring the Florida Keys in 2025!

What’s your favorite dish or drink in the Keys? Reply to this email and let us know—we’d love to feature your recommendation in an upcoming edition!

Plan Ahead: January Events You Won’t Want to Miss

Mark your calendars for these upcoming Florida Keys happenings:

• Key West Literary Seminar (Jan. 11–14): A celebration of writers and readers featuring workshops, discussions, and readings.

• Uncorked: The Key Largo & Islamorada Food and Wine Festival (Jan. 9–18): Indulge in culinary delights, wine pairings, and beachfront dining at this multi-day event.

• Florida Keys Seafood Festival (Jan. 13–14): Head to Key West for fresh seafood, live music, and family-friendly fun.

Looking Ahead to 2025

This year, we’re thrilled to bring you even more insider tips, hidden gems, and must-visit spots to help you make the most of your Florida Keys adventures. Reply to this email and let us know what topics you’d love to see featured in our upcoming newsletters—we’re here to inspire your next trip!

Here’s to another year of sunshine, salty breezes, and unforgettable road trips,
Brian

Florida Keys Road Trip Team