The Florida Keys are an island chain in the southernmost part of the United States. Each island has its own distinct personality, but the most popular for visitors are Key Largo, Islamorada, Marathon, and Key West. It takes around 2.5 hours to drive from the top of the islands to the bottom, via Henry Flagler’s bridges.
Visit during the area’s festivals, like the Humphrey Bogart Film Festival, which honors the legacy of the Key Largo star and the area. There’s also the Key West Food and Wine Festival, Conch Republic Independence Celebration and the Hemingway Days Festival, among many others.
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What to Do
John Pennekamp State Park– This park offers snorkeling and diving to the famous “Christ of the Abyss” underwater statue. It’s made up of over 70 nautical miles including mangroves and hammock trees. 102601 Overseas Highway, Key Largo
Laura Quinn Wild Bird Sanctuary– What started as a rescue operation is now an attraction that houses birds that can no longer be released into the wild. Some are tropical species like parrots while others are native to the Keys. 93600 Overseas Highway, Tavernier
The Turtle Hospital– Another wildlife-related attraction is the nation’s foremost hospital and rehabilitation facilities for turtles. They offer tours of the hospital as well as the tanks where the non-releasable turtles live. 2396 Overseas Highway, Marathon
National Key Deer National Wildlife Refuge– See the unique Key Deer, a small species that is native only to the islands. They’re protected in the refuge. A visitor’s center educates on these and other unique animals that live here. 28950 Watson Boulevard, Big Pine Key
Bahia Honda State Park– This park has scenic viewpoints, beaches, campsites, birdwatching, and boat ramps as well as gear rentals. It costs $8 to enter the park but is worth it. 36850 Overseas Highway, Big Pine Key
Ernest Hemingway Home & Museum– Tour the home where Hemingway lived with his family in the 1930s. Meet the current residents, a gang of polydactyl cats that the writer named after Hollywood legends. 907 Whitehead Street, Key West
Truman Little White House– Harry Truman spent time in this former Naval base in Key West after his decision to drop the atomic bomb. The house features artifacts from his life and career. Get your tickets here. 111 Front Street, Key West
Classic Harbor Line– Take a sunset cruise aboard the Yacht Beacon, a 1920s style boat. The two-hour cruise includes appetizers and a cash bar as you look for dolphins and watch the sunset. 202 William Street, Key West
Dry Tortugas National Park– Take the ferry to Dry Tortugas National Park from Key West for a day of snorkeling, laying on the beach and exploring Fort Jefferson. You can also skip the ferry and go by catamaran tour. Key West Ferry Terminal, 100 Grinnell Street, Key West
Southernmost Food Tasting & Cultural Walking Tour– Taste some of Key West’s best dishes including Key Lime pie and conch fritters from a local expert. The tour stops at six different restaurants around the island.
Key West Mangrove Kayak Eco Tour– Take a kayak through the “backcountry” surrounding Key West through the mangrove trees. There are countless opportunities to spot wildlife along the way. Morning and afternoon tours are available.
Key West Hop-On Hop-Off Trolley Tour– The “Conch Train,” as this green and orange trolley is known, is the best way to see the island and learn about its history in a hurry. It’s especially popular with cruise passengers since Key West is a cruise terminal for Caribbean-bound boats.
Scuba diving- Diving in the Florida Keys is some of the best in the world. You can find dive companies on every island, but I chose Rainbow Reef in Key Largo and had a great time. Lost Reef Adventures runs from Key West. Get your dive certification here and give back by volunteering in coral reef restoration.
Deep sea fishing– Islamorada is similarly known for its fishing. There are a number of half or full day fishing charters throughout the Florida Keys for mahi mahi, tuna, sailfish, and marlin.
Where to Eat
Key Largo Conch House– As the name implies, this restaurant is known for its conch fritters. But they also serve incredible key lime pie, fish tacos, and lobster bisque. They’ve been featured on Man vs. Food and also serve breakfast. 100211 Overseas Highway, Key Largo, (305) 453-4844
Sundowners– Open since 1985, this is the perfect place to watch the sunset over a local beer and fresh local seafood. Enjoy the hogfish in a spicy sauce or local seafood topped in a key lime and Tabasco butter sauce. 103900 Overseas Highway, Key Largo, (305) 451-4502
Mrs. Mac’s Kitchen II– The former diner serves the best key lime pie in Key Largo along with seafood hoagies and burgers. Wash it all down with a “Famous Key Lime Freeze,” a milkshake-type lime beverage. 99020 Overseas Highway, Key Largo, (305) 451-3722
Chef Michael’s– This Islamorada fine dining restaurant is known for its steaks and fresh local seafood. Choose your fish, which can be prepared in a number of ways. Pair with one of the many wines available. 81671 Overseas Highway, Islamorada, (305) 664-0640
Castaway Waterfront Restaurant- This longtime dockside restaurant was the first in the United States to serve the invasive lionfish. They have seafood in a variety of ways, but it’s their sushi that is the most unique. 1406 Ocean View Avenue, Marathon, (305) 743-6247
The Stoned Crab– Sustainable seafood is the draw at this waterfront restaurant. As the name implies, they offer stone crab when available and diners can feed the sharks while they wait for their meals. They also have a “green” cocktail menu. 3101 N. Roosevelt Boulevard, Key West, (305) 294-4350
Blue Heaven– If you only go to one restaurant, make it this one but go early. The former house and grounds now serve dishes like lobster benedict, banana bread, and whole fried yellowtail snapper. 729 Thomas Street, Key West, (305) 296-8666
Garbo’s Grill– I didn’t expect to find food trucks in Key West, but this taco truck serves up delicious and spicy varieties within walking distance of the historic district. Try the fish tacos, Korean barbecue tacos and Jerk chicken quesadillas at this lunchtime-only joint. 409 Caroline Street, Key West, (305) 304-3004
Harpoon Harrys– This offbeat diner and tavern is well located in Key West and has open mic nights and a full bar. They put a tropical spin on typical diner fare and the Reuben is tasty, but bring cash. 832 Caroline Street, Key West, (305) 294-8744
Where to Stay
Baker’s Cay Resort– Set on 13 waterfront acres, this eco-friendly resort has two restaurants and bars, two pools, nature trails, and a salon. Rooms have balconies overlooking the ocean where guests can borrow paddleboards and kayaks. Read our review here. 9700 South Overseas Highway, Key Largo
Jules Undersea Lodge– This is the most unique stay on the island and the “world’s only underwater hotel.” They offer scuba diving certification, rooms only accessible by water, and even have food delivered! 51 Shoreland Drive, Key Largo
Amy Slate’s Amoray Dive Resort– This resort is another favorite for diving and staying with rooms and suites. All have microwaves, televisions, and coffee makers. They also offer snorkeling and other activities. 104250 Overseas Highway, Key Largo
Hawk’s Cay Resort– One of the best for family activities, Hawk’s Cay has countless things to do from scuba diving to fishing to kids camps. They also have rooms, suites, and villas depending on your group size. 61 Hawks Cay Boulevard, Duck Key
Cheeca Lodge & Spa– Sport fishermen love this 200-room resort for its pier and marina, but they also have a spa, golf course, three restaurants, and activities like snorkeling and cycling. 81801 Overseas Highway, Islamorada
Postcard Inn Beach Resort & Marina– This retro-style resort has funky decor, WiFi, and flat-screen televisions. They have rooms and cottages as well as a marina with a tackle shop, a pool, and restaurants. 84001 Overseas Highway, Islamorada
Parrot Key Resort– Located just outside the main area of Key West, guests have access to their own porch, multiple pools, and a bar and restaurant. The hotel also has a shuttle to Duval Street and onsite parking. 2801 N. Roosevelt Boulevard, Key West
Seashell Motel and International Hostel– As one of the few hostels south of Miami, the Seashell welcomes budget travelers. There are both dorms and private rooms, along with a kitchen and easy access to Duval Street. 718 South Street, Key West
Coconut Mallory Resort and Marina– The Diamond Resorts property near the bridge to the island has everything you need, including two pools, a playground, bike and other equipment rentals, and a marina with boat slips. 1445 South Roosevelt Boulevard, Key West
Camping- Check out the state parks like Bahia Honda and John Pennekamp as well as privately owned campgrounds like Riptide RV Resort and Motel in Key Largo and Geiger Key Marina in Key West. Both tent and RV sites are available.
Rentals- Rent a waterfront house in one of the upper Keys or one of the quaint Victorian homes in Key West on Airbnb, especially if you’re traveling with a group. Ocean Pointe Suites at Key Largo is a Diamond Resorts rental property.