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The Ultimate Florida Keys Vacation Guide

Thinking about traveling to the Florida Keys? We don’t blame you! This string of tropical islands just off the southernmost tip of the Sunshine State is a haven for boating, fishing, snorkeling, scuba diving, and so much more. Vibrant art and culture scene? Check. World-class dining? Done. Great nightlife? You bet. 

Now, before you pack your bags and slather on the sunscreen, let’s make sure you’re ready to take advantage of everything this stunning archipelago has to offer. Our handy guide to Florida Keys travel covers the best spots to eat and activities to enjoy, plus the perfect places to stay while you’re there. With ideas for Key West, the Middle Keys, and Islamorada, we’ve done the legwork for you so you can enjoy every minute in this sun-seekers paradise.

Ready to suit up and go? Keep reading to get our expert picks on all things Florida Keys.


biking in Key West

KEY WEST

What to Do

Key West offers that perfect combination of adventure and relaxation—with a distinctly tropical flavor. Start your day with a snorkeling or scuba expedition and witness a kaleidoscope of colors beneath the crystal-clear waters of the Gulf of Mexico. Rent a bike—or make like a local and rent a golf cart—for a leisurely afternoon exploring the historic part of town, especially Duval Street’s quaint boutiques, lively bars, and inviting restaurants. Take a tour of Ernest Hemingway’s home, or for something a bit more active, try a kayak trip through the mangroves. Afterward, kick back on a stretch of pristine sandy beach or set sail on a sunset cruise, where you can savor the magic as the sky ignites with vivid hues.

Key West from overhead

Where to Indulge

For a true taste of the island, head to Key West Legal Rum. Here, on the site of a former Coke bottling facility, longtime Key West resident Paul Menta runs the area’s first legal rum distillery. Part chef and part distiller, Menta has wowed locals and visitors alike with his expertly crafted Cuban mojitos that pair perfectly with the cuisine of South Florida.

Key West Legal Rum owner Paul Menta with his signature Cuban mojito

And it wouldn’t be a trip to Key West without sampling the island’s namesake dessert, key lime pie. We recommend trying the frozen, chocolate-covered variation from Kermit’s Key Lime Shoppe.

Where to Stay

Sunset Key Cottages is a private island resort located off the west coast of Key West, which you can access via ferry. With 40 guest cottages, a luxe spa and an award-winning restaurant, it’s the perfect spot for relaxing on the beach, taking a hammock nap, or sipping on a cocktail at Latitudes while you watch the sunset.


family at Bahia Honda State Park in the Florida Keys

THE MIDDLE KEYS: SUGARLOAF KEY, BAHIA HONDA & MARATHON

What to Do

Whether you’re traveling solo or with family, there’s no better spot for a beach day than Bahia Honda State Park. Situated alongside the iconic railroad bridge built by Henry Flagler, Bahia Honda is recognized as one of the Keys’ best beaches. Here, you can easily spend a full day snorkeling, swimming, building sandcastles, and catching some rays.

In Marathon, get back to nature with a kayaking excursion through the mangroves off Sombrero Beach. Fun fact: Sombrero Beach is a nesting beach for loggerhead turtles, who come to lay their eggs at night from April through October. 

Where to Indulge

Just south of the Seven Mile Bridge in Sugarloaf Key, you’ll find chef Paul Kapsalis and a restaurant with an unforgettable moniker: South of the Seven. Here, Kapsalis curates a delectable menu of fresh local seafood accompanied by tropical fruits and unexpected touches, like fresh bao buns.

South of the Seven restaurant in the Florida Keys

Where to Stay

If you’re celebrating a special occasion—or just want to make it an unforgettable trip to the Florida Keys, Little Palm Island is one of those bucket-list experiences you have to see to believe. Located on Little Torch Key, the adults-only resort is accessible by boat or seaplane and is limited to 60 guests. Make the most of your stay with an over-the-water massage, dinner served on one of the island’s sandbars, or an ultra-romantic turndown service. A hot-drawn bath for two with rose petals? Yes, please.


Islamorada's turquoise waters from overhead

ISLAMORADA

What to Do

Surrounded by breathtaking turquoise waters and pristine white sandy beaches, Islamorada offers a myriad of unforgettable experiences for every traveler. Dive into the vibrant underwater world of the Florida Reef, the only living coral barrier reef in the U.S., and explore its mesmerizing marine life on a snorkeling or scuba diving trip. Embark on a thrilling fishing expedition and see why Islamorada is considered the Sportfishing Capital of the World. Who knows—maybe you’ll reel in the catch of a lifetime! For a taste of local culture, visit the History of Diving Museum. Then head to Robbie’s Marina, where you can charter a boat for snorkeling and exploring the sandbars. Bonus: You can feed the tarpons from the marina, too, which is a hit with young travelers.

Where to Indulge

Islamorada is home to Florida Keys Brewing Co. and Islamorada Brewery & Distillery, two spots where you’ll find plenty of options to cool you down after a long day of fun in the sun. From craft beers to cocktails made from spirits distilled on-site, the menus at both cover all your favorites so you can kick back and enjoy island time.

Where to Stay

The colorful beachfront casitas and stunning villas at La Siesta Resort are an ideal home base for your Islamorada adventures. With private walk-in beaches and plenty of pools to choose from, you’re guaranteed to find a perfect spot to splash and sunbathe. Take a bike ride, curl up in a hammock with a book, or explore the bars and restaurants at La Siesta and its three sister resorts just down the road. 


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