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Ahhh, the Florida Keys. They’re relaxing, they’re surrounded by water on all sides, and if you don’t have a rum runner in your hand at all times when you’re there, you’re doing it wrong. They’re divided into the Upper, Middle and Lower Keys, and together, this palm-fringed archipelago spans 113 miles, all connected by only one road: The gorgeous U.S. 1-Overseas Highway. What most people don’t know, however, is that, while it only takes three hours to drive from one end to the other, The Keys are actually made up of 1,000-plus islands. To find out which ones are for you, checkout our guide to our favorite keys below (and stop in every other key in between).

RELATED: How to island hop the Keys by seaplane

From north to south, here’s where to go when…

You just want to escape the city: Key Largo

The unofficial “grand entrance” to the Florida Keys, Key Largo is just an hour south of Miami—but when you get there, you feel like you’re in a whole other world. In quiet Key Largo, life is all about the water. It’s bordered by Florida Bay and the Atlantic Ocean, and it’s home to John Pennekamp Coral Reef State Park, which is a part of the Florida Keys National Marine Sanctuary and home to the oldest underwater preserve in the U.S. It’s both the longest key and a hub for South Florida water sports, so go here for scuba diving, snorkeling, sport fishing, kayaking, paddle boarding, boating and more.

Where to stay: Get comfy at Playa Largo, a luxury Autograph Collection hotel at Mile Marker 97 that fuses the modern conveniences of the Magic City with that “je ne sais quoi” about the serene Florida Keys. As soon as you walk in, the valet attendant will hand you one of the hotel’s signature pineapple mojitos. From then on, trust us: You’re in paradise.

…you don’t want to drive all the way to Key West: Islamorada

Halfway between Key Largo and Key West, Islamorada, or “Purple Island,” is among the archipelago’s most popular key. Just a 90-minute drive from Miami, it’s also a perfect stopping point on the way down. When you’re on this key, go bike riding, take an eco-tour, or go sportfishing; Islamorada is considered the “sportfishing capital of the world,” after all! If you like history, hop on a boat and visit Indian Key and Lignumvitae Key, where you’ll find early Indian settlements and one of Florida’s only tropical hardwood hammocks. On Purple Island, there are endless bars and restaurants, from casual to trendy, as well as a range of no-name to luxurious hotels.

Where to stay: Of all the hotels, there’s one boutique, beach-chic getaway that’s not to be missed: Amara Cay Hotel. It’s right on the Atlantic side of the key, is home to Sparrows Rum Bar, and has hanging chairs in the lobby that practically beg you to swing.

…you feel like exploring: Marathon

Marathon is a mini archipelago of its own. Marathon is actually made up of East and West Sister’s Island, as well as a collection of smaller keys, like Boot, Knights, Hog, Vaca, Stirrup, Crawl, Little Crawl, Deer, Fat Deer, Long Pine and Grassy Key. Touted as being the busiest and most family-friendly parts of the archipelago, it’s filled with everything from golf, scuba diving, and snorkeling, to boating, kayaking, SUP paddling, and more. If you’re there in the spring, don’t miss the annual seafood festival in March, or the tarpon tournaments starting in April. Sombrero Beach sits right on the Atlantic Ocean, and is a good place to go for a picnic, play volleyball, find loggerhead turtles, or just to spend the day basking in the sun. Crane Point has nature trails and hardwood hammocks, while old-fashioned Key Colony Beachcalled “the gem of the Florida Keys”has adorable local shopping and tasty restaurants, like the waterfront Sparky’s Landing, where the motto is: “Eat, drink, and be merry, for tomorrow you may work.” (Valid.)

Where to stay: The name says it all at Tranquility Bay Beachfront Hotel & Resort. Located right next to the turtle hospital, the resort literally puts the ocean at your front door with a private beach, plus a restaurant and bar.

ALSO: What’s the Key to racking up travel rewards quickly? It’s Orbitz Rewards!

…you’re obsessed with nature: Big Pine Key

Floating at the west end of the Keys’ famed “Seven Mile Bridge,” Big Pine Key is where you go for a low-key (get it?) vacation. Dubbed one of the “Natural Keys,” Big Pine was practically made with nature lovers in mind. It’s entirely overgrown; just five nautical miles from Looe Key, a National Marine Sanctuary; and is home to the adorably-native Key deer, a subspecies of the white tail deer. These friendly, dog-sized creatures are so popular that one of the hottest hotels on Big Pine, Deer Run Bed & Breakfast, is named after them.

Where to stay: Get charmed at Deer Run Bed & Breakfast, a charming four-room eco-friendly haunt that’s all vegan, boasts direct ocean views, and even has an honor-system refrigerator with wine coolers in the cozy common area.

…your idea of a “hotel” is camping: Bahia Honda

When Henry Flagler built the railroad from Jacksonville to Key West in 1912, every key in between became a place worth discovering. Nowhere is that more true than Bahia Honda! Once just a remote island, today, all of Bahia Honda Key is an award-winning, 500-acre state park. Go here for picnicking, swimming, boating, kayaking, snorkeling, coral reefs, bird watching, and even to wander through the park’s onsite Sand and Sea Nature Center.

Where to stay: At Bahia Honda State Park, you can reserve a cabin or bring your tent—there aren’t any hotels here, but camping is huge.

…you think you deserve a fancy weekend: Little Torch Key

Named after the torchwood tree, lush Little Torch Key was once a frequent fishing destination for President Harry S. Truman. Still a popular fishing and kayaking destination today, its backcountry feel is all part of Little Torch Key’s charm. Perfect for exploring the colorful corals of the Looe Key National Marine Sanctuary, this key floats just 29 miles north of Key West, making it a popular place to stay for day trips to its more lively neighbor.

Where to stay: And speaking of sleeping, when it comes to hotels, bring your S.O. and go off the map for a weekend steeped in romance. From this key, you can hop on a 15-minute ferry ride to Little Palm Island, an exclusive private island resort with 30 oceanfront bungalows, romantic canopy beds, little cell service, outdoor showers, personal hammocks, a torch-lit restaurant in the sand, massage beds that are actually in the ocean, and friendly Key deer who will eat and drink right out of your hands.

you want to blow off steam: Key West

Unless you’ve been living under a rock, you’ve already heard of famed Key West. The final key in Florida, this party-all-night island has made its mark as both America’s southernmost city and (especially important in South Florida) the part of the U.S. that’s closest to Cuba. Packed with history, it’s where you’ll find Ernest Hemingway’s house and the Mel Fisher Maritime Heritage Society Museum, which has a rare collection of gold and silver treasures found in 17th-century shipwrecks off the coast of Florida. Everything in Key West is colorful, from the lush tropical gardens, pastel-colored homes, and architecturally-rich inns and hotels, to the “Conchs,” as the locals themselves, many of whom have lived here since birth. A cultural town before anything else, Key West is stocked full of local bookstores, art galleries, eclectic restaurants and even local theaters. No matter what you do during the day, at sunset, the only place to be is Mallory Square. Every night, musicians, jugglers, mimes, fire eaters, and food vendors gather here to dance and celebrate the sun setting over the water… which is a must-do when you catch those views.

Where to stay: Spend your nights at The Perry Hotel Key West, a brand new hotel featuring a marina, an outdoor pool, and free area shuttle to help you bar hop carefree.


Tagged: Florida

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Jennifer Agress

Jennifer Agress

Jennifer is a Miami-based writer and editor who loves good food, a better martini and traveling every chance she gets. She writes about luxury travel, dining and lifestyle for Travel Weekly, Private Air Luxury Homes, Preferred Travel, Modern Luxury Weddings, INDULGE Miami, Thrillist, NUVO Magazine and more. When she’s not on a plane, she’s likely plotting her next adventure—follow @JenniferAgress on Instagram to see where she lands.

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