Your Cheat Sheet to the Top Destinations in the Florida Keys

The Florida Keys is a 125-mile archipelago consisting of around 1,700 islands, though less than 50 are connected and accessible by the famous Overseas Highway. As you drive from Key Largo to Key West, many of the smaller Keys (technically known as “cays”) pass by in the blink of an eye, while others make a living as full-blown destinations. The smaller Keys are often lumped in with their big brothers and sisters for ease. For further simplicity, the Keys are often divided and referred to as five different areas: Key Largo, Islamorada, Marathon, Big Pine Key (or the Lower Keys), and Key West. Though relatively close together and sporting similar surroundings, the Keys have remarkably different draws. The driving distance from top to bottom can clock in at over two hours, so it’s important to pick the right Key to use as a home base. This cheat sheet to the Florida Keys will help you choose the island that’s best for you, whether you’re looking to party or just chill at the beach.

1. Key Largo

Beach at Key Largo Bay Marriott Beach Resort

Beach at Key Largo Bay Marriott Beach Resort; Oyster

Key Largo may be the northernmost Key, but it’s the best place for folks who want to get below the water’s surface. For starters, it’s home to John Pennekamp Coral Reef State Park, a protected underwater marine park that includes one of the only two living reef systems in the U.S., underwater statues, and excellent snorkeling, scuba, and glass-bottom boat tours. Lines can be long, as this is one of the most popular state parks in Florida, but the warm water, colorful fish, and possible eagle ray sightings are well worth it. Diving enthusiasts can even check into the Jules’ Undersea Lodge, where you have to suit up and dive down to enter the guest rooms. There’s also plenty to see above the surface, with fishing charters, dolphin cruises, the Laura Quinn Wild Bird Sanctuary, great nature trails, and, of course, spectacular sunsets. 

Our Key Largo Hotel Pick: Kona Kai Resort, Gallery & Botanic Garden

2. Islamorada

Beach at Chesapeake Beach Resort

Beach at Chesapeake Beach Resort; Oyster

This laid-back, breezy Key may seem like a modest spot to lay your head, but it’s actually the fishing capital of the world. The diversity of fish available off the coast of Islamorada, which is located between the Florida Bay backwaters and the Atlantic Ocean, is practically unparalleled. The Atlantic waters are home to snapper, grouper, and swordfish, while the backwaters are brimming with tarpon, bonefish, and snook, making it a sport-fishing dream come true. It’s easy to see why new and professional anglers cast their lines into these waters.

As a bonus, this small village has a growing food scene, which means you can try all the catches of the day without lifting a fishing rod. Try the laid-back and casual Lorelei Restaurant & Cabana Bar as well as the upscale Chef Michael’s. Plus, you can taste local brews that pay homage to the Florida Keys at Florida Keys Brewing Company or Islamorada Beer Company. 

Our Islamorada Hotel Pick: Casa Morada

3. Marathon

Marina at Banana Bay Resort and Marina Marathon

Marina at Banana Bay Resort and Marina Marathon; Oyster

Overall, Marathon is the perfect home base for folks looking to explore the region to the fullest. The island is located smack in the middle of the Florida Keys, cutting down on drive times for anyone planning to visit a combination of spots in the Upper, Lower, and Middle Keys. Traveling by boat? Take advantage of Marathon’s many wet and dry slips. Boaters can dock directly into over 2,400 slips situated at Marathon’s marinas, restaurants, and hotels. However, if you are driving, be sure to take the scenic, historic route across Marathon’s famous Seven Mile Bridge, or just do as the locals do and cast a line off the side and fish for wild, wide-mouthed tarpon. 

Marathon is also a popular spot for families who prefer easy, low-key, and educational vacations that blend history, nature, activities, and good food. Top family-friendly activities include visiting the world’s only veterinary-certified turtle hospital, taking a SUP or kayak tour around mangroves, enjoying theater shows, checking out museum exhibitions, and eating at any of the tasty food festivals hosted on the island. Speaking of food, be sure to get your fill of locally-harvested fish, stone crabs, lobster, and of course, Key lime pie.

Pro tip: Marathon is also your spot if you’re looking for beautiful white-sand beaches, often a rarity in the Florida Keys. Sombrero Beach and Coco Plum Beach are both free and open to the public.

Our Marathon Hotel Pick: Tranquility Bay Beach House Resort

4. Big Pine and Lower Keys

Marina at Big Pine Key Fishing Lodge

Marina at Big Pine Key Fishing Lodge; Oyster

Much of what the Florida Keys offers is rooted in nature, both on land and sea, though Big Pine Key and its neighboring Lower Keys are where you want to be for the most memorable nature-filled adventures. In fact, these Lower Keys are nicknamed “the Natural Keys” because of their preserved beauty and access to natural areas. One of our favorite spots is the National Key Deer Refuge, where visitors have the chance to spot Key deer, a tiny white-tailed deer only found in the Florida Keys, and go for hikes through the refuge. There are also great places to go snorkeling along the reefs and opportunities to see manatees, Florida’s gentlest giants. 

Other great nature activities include kayaking through mangrove forests and over seagrass flats, bird-watching, observing herons on the shore at the Great White Heron National Wildlife Refuge, and seeing freshwater wildlife at the Blue Hole (keep your eyes peeled for alligators, turtles, and colorful birds). Looking for a less active natural experience? Head to Bahia Honda State Park for one of the Keys’ best beaches.

Our Big Pine Key Hotel Pick: Big Pine Key Fishing Lodge

5. Key West

Key West, Florida

Key West, Florida; Oyster

Key West has a long history of being the most popular and most-visited Key, even though it’s the farthest south. This city is proud of its quirkiness, and once staged a fake war against the United States using conch fritter bombs, threatening to become its own country. If you like irreverent fun, lively bars, souvenirs, and historic buildings, this is your spot. Key West has a more corporate lean, with Margaritaville and other chain restaurants, but it’s still loaded with hometown favorites like Blue Heaven and the Green Parrot dive bar. It’s also worth noting that cruise ship passengers, bachelor parties, and spring breakers often flock to the popular bar-lined Duval Street and Mallory Square’s waterfront restaurants.

Key West is split into two parts: Old Town and New Town. Old Town is full of history, bars, and much of what most visitors to Key West have been coming to see for years, while New Town highlights some of Key West’s fresher developments and spots that nod to the city’s history.

Smoke Cuban-inspired cigars and taste local rum cocktails at Rum Row, visit the cursed doll inside an old fort-turned-museum, charter a boat or hand-feed tarpon at Charter Boat Row, or soak up the sun on Smathers Beach, one of the only non-rocky beaches in Key West. The destination offers an eclectic mix of things to do, from visiting the clothing-optional bar of Garden of Eden to checking out Hemingway’s old house to jet-skiing over the water. 

Our Key West Hotel Pick: The Gates Hotel

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