This 125-mile Florida Island Chain Has Gorgeous Beaches, Fresh Seafood, and Stunning Hotels

The Florida Keys are like a coral kingdom: a 125-mile chain of islands flung south from the tip of Florida with the ultimate island — Key West — resting just 90 miles from the shores of Cuba. And with one narrow road (and 42 bridges) connecting the isles, just to travel the Florida Keys is to feel on a magical, water-surrounded journey.

“There are a variety of reasons to choose the destination, including a wide range of accommodations to meet every style; fresh, local cuisine with a Caribbean flair; water-based activities like sailing and kayaking or paddleboarding; and the best part is access to a world of adventure and romance without needing a passport,” Stacey Mitchell, director of the Florida Keys & Key West tourism board, told Travel + Leisure. She noted that a trip to the Florida Keys “rivals even the most popular island destinations.”

While it's possible to hop in a car in Miami and make it to Key West (and the southernmost point in the continental United States) in less than four hours (traffic willing), that defeats the charm and richness of the Florida Keys. Every few miles there's a discovery to be had: a tiki bar, a seafood joint, a beachy resort or boutique hotel, a gorgeous nature preserve, or just a thrilling turquoise vista across the famed saltwater flats toward a blue horizon. 

So, make a trip of it — spend a few days in Key Largo or Islamorada near the upper end of the archipelago, dally on Marathon or Big Pine Key, and then settle in for some serious quirky culture, history, and bohemia in Key West. Take time to snorkel, dive, and fish, walk the beach, and eat lots and lots of seafood and Key lime pie. And don't worry if you don't get to everything that there is to love and explore in the Florida Keys — you'll be back.

To help guide you on your journey, Mitchell recommended “the Florida Keys and Key West travel app which has several great suggestions for places to stop along the Overseas Highway and also gives a guided historical overview.”

Best Hotels & Resorts

Key Largo

The Bungalows Key Largo: A former trailer park on a stunning stretch of shoreline with a sandy beach has been converted to a lush enclave of small cottages with big luxuries, including private verandas with plunge tubs and outdoor showers. At The Bungalows, there are six restaurants and bars on the property — including a toes-in-the-sand Mexican cantina and a savvy bar with a Hemingway vibe — and a top-notch spa. A panoply of water activities including catamaran excursions make it easy to stay put. Adults only, all-inclusive, and all just 63 miles from Miami International Airport.

Islamorada

The Moorings Village: This former coconut plantation re-emerged in the 1960s as a small resort. Today, its aqua-shuttered estate house and sugary stretch of white sand — famously peppered with a grove of listing palms — are straight-up cinematic, and its collection of luxury cottages make for an Old Florida idyll.

Marathon

Isla Bella Beach Resort: This luxury resort on Marathon Key is a game-changer, with ocean views from every room and suite and a high-design feel. The property is set on a mile-long stretch of private beach and surrounded by more than a thousand palms. Five pools, exceptional dining, and an open-air bar with a killer sunset view complete the fantasy.

Big Pine and Lower Keys

Little Palm Island Resort & Spa: The only private island resort in the United States is hidden away in the Lower Keys. The adults-only enclave is accessible by boat and seaplane and features just 30 thatched-roof bungalows with updated interiors (including floor-to-ceiling glass doors and outdoor copper soaking tubs). To round out the offerings there is a world-class spa with a two-story atrium, private poolside cabanas, and some of the best cuisine in the Keys.

Key West

Parrot Key Hotel & Villas: Parrot Key Hotel & Villas may be the ultimate Key West hideaway. The property is hidden off a main drag and completely enveloped in five acres of tropical greenery with four swimming pools and a stretch of beach. The feel here is serene and sophisticated, but without airs.

Best Things to Do

Key West

John Pennekamp Coral Reef State Park: This state park is a must for snorkelers and divers alike (and if you don't swim, there are always the glass-bottom boat tours). The park’s 70 nautical square miles form the first undersea park in the U.S. and while the upland areas sport mangrove swamps and tropical hammocks, it's the coral reefs that are worth suiting up for (and don't forget, the waters of the Keys are always warm, even in the depths of winter). Join a snorkeling or scuba tour or rent a kayak, paddleboard, or canoe.

Marathon

Turtle Hospital: Leave the old-school petting aquariums behind and fall in love with the residents in rehabilitation here at the first state-licensed veterinary hospital devoted solely to the treatment of endangered sea turtles in the world. The tours are excellent and well worth booking in advance.

Big Pine Key

National Key Deer Refuge: They're tiny, adorable, and unique to the Florida Keys. And now these miniature Key deer are protected, having been saved from the brink of extinction. Start at the visitor and nature center for more on the Key deer, including where to see one and how to explore the refuge's preserved forest, tropical hardwood hammocks, freshwater and salt marsh wetlands, and mangrove forests.

Key West

Honest Eco Sustainable Nature Tours: Key West is full of cruise charters, but this progressive tour company is head and shoulders above the rest for its commitment to sustainability and environmental education. Owned and operated by biologist Billy Litmer, Honest Eco operates out of the Historic Seaport and features SQUID, Key West's first electric power charter boat. Schedule a dolphin watch and snorkel or an “All the Above” trip, which also includes kayaking and organic vegetarian lunch.

Key West Pro Guides: Ready to live that sportfishing dream? The team at Key West Pro Guides can help even a fishing novice get the Hemingway experience on the water — and they're ready to help experts land that trophy fish. “Without a doubt when someone comes to the Florida Keys for the first time, they should get out on the water whether it’s via a fishing charter or snorkel excursion,” said Mitchell.

Best Shopping

Key Largo

Shell World: Kitschy and over the top, this is a classic Florida Keys tourist stop, but it's truly worth it. Take in the splendor, pick up a souvenir, and know that you're part of a great tradition of roadside attractions.

Islamorada

Village Square at the Trading Post: A charming collection of pastel cottages is home to an equally charming collection of shopping and snacking: You'll find some beachy boho fashion, home décor, plants and other botanicals, art, burritos, and coffee.

Key West

Books & Books: This lovely indie bookstore — and nonprofit and community center for readers and writers — was co-founded by beloved author (and Key West resident) Judy Blume and is ground zero for Key West's literary scene.

Gallery on Greene: For collectors and oglers, Nance Frank's gallery with a deep bench of Key West artists (including a stellar roster of Cuban artists) is a must-visit.

KINO Sandals: It's rare that a souvenir is truly a local favorite as well, but you won't find a Conch (Key Wester) who doesn't have a perfectly broken-in pair of these leather sandals. Hit the landmark shop founded by Cuban immigrant Roberto "Kino" Lopez in 1966 and gape at the 17 designs and myriad shades (you can also watch them being made).

Best Restaurants

Key Largo

Key Largo Conch House: Let this family-owned institution be your introduction to the conch fritter, a Florida Keys specialty. And if you're in a breakfast mood, tuck into a stack of Key lime pancakes.The Conch House was one of the first restaurants recommended by Mitchell, who noted that the spot is a local favorite.

Islamorada

Lorelei Restaurant & Cabana Bar: It's all about catching the sunset and some live music at this toes-in-the-sand favorite, reveling in local delicacies like the house-smoked fish dip and Key lime peppercorn snapper. The "Frozen" Key Lime Pie on the dessert menu is renowned.

Marathon

Keys Fisheries: There's nothing better than a seafood dive that’s next door to one of the coast's largest fish exporters, and this salty classic is pure Keys fun (get the stone crabs when they're in season). The Lobster Reuben and Key lime pie are famous (and rightly so), so bring your appetite.

Big Pine and Lower Keys

South of the Seven: If you're wondering, the name means you're south of the Seven Mile Bridge that marks the Lower Keys. Feel like an insider? Now it's time to celebrate with big picture window views of the water and the Mediterranean-inspired menu in this go-to spot inside the landmark Sugarloaf Lodge. Mitchell calls South of the Seven one of the Keys’ “off-the-beaten-path hidden gems.”

Key West

Blue Heaven: With its dense foliage and quirky décor, this Key West landmark is the bohemian hangout of choice, whether hitting the little stand-up bar for happy hour or taking a table for a whole blissful brunch, lunch, or dinner. Yes, the rooms upstairs were once a bordello, and yes, Hemingway refereed boxing matches here, and yes, the Key lime pie is the tallest (and most delicious) you've ever seen.

Best Time to Visit

The climate in the Florida Keys is subtropical, and the proximity to the Gulf Stream and Gulf of Mexico means that the average summer and winter temperatures rarely differ more than 10 degrees. The result is a year-round paradise — except for hurricane season which typically starts in early June and ends in late November. 

“The winter and spring seasons are among the best times to visit as the weather is cooler and the water temperatures are delightful,” said Mitchell, who noted that “even when the weather is hottest in South Florida, the air in the Keys is still a few degrees cooler.”

Most tourists visit between late December and May. During this time it almost never rains, and even if clouds do push through with some showers, they're gone that day. 

How to Get There

Most out-of-state travelers get to the Keys by flying into Miami International Airport (MIA) and then hopping in a Florida Key-bound shuttle or taxi. But, the Keys are also home to two international airports of their own: Key West International Airport (EYW) and Florida Keys/Marathon International Airport (MTH). 

It’s worth checking all three airports when pricing out your flights.

Islands to Visit

The Keys are divided into five regions: Key Largo, Islamorada, Marathon, Big Pine and Lower Keys, and Key West.

Key Largo: This island is known as “the dive capital of the world” and is home to John Pennekamp Coral Reef State Park, the first underwater preserve in the U.S.

Islamorada: Islamorada is famous for its backcountry sport fishing and saltwater fly fishing. The Seven Mile Bridge at Marathon is one of the longest segmented bridges in the world.

Big Pine and Lower Keys: Big Pine Key is home to a national refuge that protects the miniature endangered Key deer, which has made an astonishing comeback from near extinction.

Key West: This island is famous for the writers who once lived there — most notably, Ernest Hemingway and Tennessee Williams — and the warm and welcoming LGBTQIA+ scene. Key West is closer to Cuba (90 miles) than it is to Miami (159 miles) and is home to a vibrant historic district, an international airport, and marks the southernmost point in the continental United States.

How to Get Around

Renting a car in the Key can be convenient — until it’s not. Traffic and hard-to-find parking are two very real factors to consider. If you can avoid renting a car, you should. Here’s how:

Shuttles: Keys Shuttle and Florida Keys Express Shuttle offer door-to-door shuttle services to the Keys from Miami International Airport.

Bus: The Greyhound Keys Shuttle connects various stations in Miami with the Keys — all the way down to Key West. On Key West, the Duvall Loop is a free bus service with 18 stops in Old Town.

Taxis: Local cab companies generally service their island area — inquire locally for taxis. A cab stand services passengers arriving at Key West International Airport (EYW) and Freebee in Islamorada has a fleet of on-call electric vehicles.

Ridesharing: Uber and Lyft both operate in the Florida Keys.