May in the Keys: Sun, Sips & Celebrations from Mile Marker 106 to 0

Dear Road Trippers,

May has officially arrived in the Florida Keys—and with it comes that sweet, sunny shift into early summer. The water gets warmer, the sunsets burn a little brighter, and every island from Key Largo to Key West feels like it’s waking up with a cocktail in hand. 🍹

This week, we’re giving you everything you need to kick off the season—Cinco de Mayo fiestas, waterfront adventures, live music, and ice-cold drinks all wrapped in island charm.

Ready to coast into summer? Let’s ride.

🎉 Where to Celebrate Cinco de Mayo in the Florida Keys

Tacos 🌮. Tequila 🍸. Turquoise water 🌊.
If you're spending May 5 anywhere along the Overseas Highway, here's where to turn your road trip into a full-blown fiesta:

🏖️ 1. Bungalows Key Largo – All-Inclusive Fiesta Paradise

📍 99010 Overseas Hwy, Key Largo

Escape to one of the most luxurious resorts in the Upper Keys and enjoy a day-long Cinco de Mayo celebration filled with tropical indulgence. Start with sunrise yoga to get your zen on, then turn up the energy with stand-up paddleboard races, margarita bar takeovers, live mariachi, and a Casa Dragones tequila ice luge (yes, really). Finish the night with a themed dinner at Sea Señor.

🕒 All-day event
🔗 See the full schedule

🎸 2. Caribbean Club, Key Largo – Classic Keys Celebration

📍 104080 Overseas Hwy, Key Largo

This legendary waterfront dive bar (you might recognize it from the movie Key Largo) is hosting a no-frills, high-vibes party featuring live music by A Couple of Wanders, a Taco Truck takeover, and frozen mezcal margaritas that pack a punch.

🕓 11 a.m. – 9 p.m.
🔗 More info here

🍻 3. Florida Keys Brewing Co. – Island-Style Bash

📍 81611 Old Hwy, Islamorada

Belly up to the bar in the colorful beer garden for a celebration full of small-batch brews and local flavor. The Taco Jalisco food truck will be serving up spicy bites to pair with over 20 beers on tap. Expect festive music, chill vibes, and maybe even a beer pong challenge or two.

🕛 All day
🔗 Event calendar

🍹 4. Hog Heaven Bar & Grill – Waterfront Fiesta

📍 85361 Overseas Hwy, Islamorada

Known for its rowdy nights and stunning bay views, Hog Heaven is going full send this Cinco with drink specials, a lively outdoor patio, and maybe even a surprise live band to keep the crowd buzzing long after sundown.

🕓 Starting 11 a.m.
🔗 Party details

⛵ 5. Fury Water Adventures – Cinco Sunset Sail

📍 631 Greene St, Key West (departure)

Hop aboard a catamaran and let the ocean breeze set the mood. Fury’s sunset sails are legendary, and on May 5th, they’re adding Mexican snacks, margaritas, and a live DJ to their tropical cruise. Expect unforgettable views of the Gulf as the sky explodes into color.

🕗 Cruise times vary
🔗 Book here

🏊 6. The Marker Key West Pool Party – Battle of the Bars

📍 200 William St, Key West

This upscale poolside party kicks off at 3 p.m. with a Margarita Showdown featuring top local bartenders, Don Julio specials, and a live DJ spinning poolside hits. It's the ultimate mix of chill and fiesta.

🕒 Starts at 3 p.m.
🔗 Event info

🌞 7 Ways to Kick Off Summer Early in the Florida Keys

Cinco de Mayo might steal the spotlight, but the whole month of May is ripe for island adventure. Here’s how locals love to lean into the season:

🌅 1. Sip & Sway at Sunset Pier – Key West

Grab a drink, find a seat on the dock, and let the ocean do the rest. Sunset Pier offers nightly live music, an unbeatable view of Mallory Square, and some of the best rum drinks this side of the equator.

🔗 More on Sunset Pier

🛶 2. Paddle the Mangroves at Curry Hammock

Tucked between Marathon and Long Key, this peaceful park is a paddler’s paradise. Glide through mangrove tunnels and explore secret lagoons in pure silence.

🔗 Plan your visit

🍦 3. Cool Down with Key Lime Ice Cream – Flamingo Crossing

After a sunny stroll through Old Town, swing by this pastel-colored scoop shop. Their key lime pie ice cream is as creamy, tart, and dreamy as it gets.

🦩 4. See Flamingos at Crane Point – Marathon

A must-stop for nature lovers, Crane Point lets you explore historic homes, nature trails, and the occasional pink-feathered guest. Bring your binoculars!

🔗 Explore Crane Point

🧘 5. Salute the Sun at the Southernmost Point

Start your day with beachside yoga and gulf breezes that feel like a hug. Several local instructors host donation-based morning sessions with ocean views.

🎶 6. Bar-Hop with Live Music on Duval

End the night the right way—with a music crawl down Duval Street. Start at Sloppy Joe’s, slide into The Green Parrot, and end with a frozen colada at The Tiki House.

🍹 7. Plan Next Week’s Road Trip: Mile Marker Magic

Next week’s newsletter is packed with the quirkiest, must-see roadside stops from Miami to Key West—including a giant lobster, a tree on a bridge, and the world's smallest bar. Stay tuned!

Wishing you salty breezes, sizzling tacos, and a Cinco celebration for the books!
Catch you next week,
Brian

Florida Keys Road Trip Team

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