There are more than 1,700 islands in the Florida Keys, stretching some 125 miles south of Miami — and you can drive the whole distance across extended bridges. Despite not being far from a major city, the archipelago has a distinct relaxed flavor that separates it from the rest of Florida. Here, it’s all about a good time, both in the sea and on dry land.
And whether you’re embarking on a romantic getaway or an action-packed family vacation, there’s more than enough to fill your itinerary in the Florida Keys. While we’ve recommended a north-to-south trajectory, you could also take this trip in reverse, starting out with the long drive to the end before slowly working your way back to Miami.
As always, check for travel restrictions and closures before planning your trip.
Friday: Hit the Water in Key Largo
Welcome to Key Largo, the gateway to the Florida Keys. It may be a short drive from Miami to Key Largo, but exploring the northernmost key requires quite a bit of energy — you’ll be spending the majority of your day in and around the water.
As any road tripper knows, it’s important to keep both your car and your body fueled up, so dine at any of Key Largo’s classic breakfast joints, like Doc’s Diner (don’t miss the homemade pancakes and waffles) or Harriette’s Restaurant (the Key lime muffin is the stuff of legend).
Then, it’s off to John Pennekamp Coral Reef State Park, the first undersea park in the U.S.
If you have your scuba certification, this is one of the best places to dive in the country. If not, don’t sweat it — you can snorkel, too, or even take a glass-bottom boat tour. At more than 70 square miles, the park has more than you’ll be able to see in a morning, but try to pull yourself away — there’s still so much to do in Key Largo!
For lunch, you’d be doing yourself a disservice if you didn’t try some seafood. Hot spots include Key Largo Fisheries Backyard Café and Hobo’s Café for those partial to grilled fresh fish, shrimp, lobster and, of course, stone crab.
In the afternoon, it’s back to the water. Don your mask and dive down to Christ of the Abyss, an underwater art installation, or Spiegel Grove, an artificial reef created from a sunken ship.
If you’d prefer to stay dry, hop aboard the African Queen Canal Cruise to wend your way through the Port Largo Canals, or visit the Florida Keys Wild Bird Rehabilitation Center, where you can visit with dozens of feathered friends and even watch a pelican feeding.
When you get hungry again, go for pizza at C&C Wood Fired Eats if you’ve had enough seafood at lunch — or Key Largo Conch House if you haven’t. For dessert, it’s time for Key lime pie — you’re in the Keys, after all. Blond Giraffe Key Lime Pie Factory is a perennial favorite.
Saturday: Explore Beaches and Wildlife in Marathon
Marathon is not as sleepy as the other keys, nor is it a single landmass — there are 13 islands within the borders of this family-friendly city. There’s plenty to do here if you want to keep busy, but this is also a top beach destination in the Keys, so you can certainly keep things more low-key and just commit to a day of lazing in the sun.
Tuck into a casual brunch at Wooden Spoon (for a classic diner moment and killer sausage gravy) or Marathon Bagel Co. (run by a pair of New Jersey transplants, so it’s a real-deal bagelry) before heading to the beach.
Visit Sombrero Beach or Coco Plum Beach to take in the sun and the sand. Afterward, venture to the Turtle Hospital or the Dolphin Research Center to see some wildlife without having to hop back in the water. If you don’t mind getting wet, consider heading to Curry Hammock State Park, off of which is a great reef for snorkeling.
Break for lunch at Taqueria La Palapa for an excellent carnitas taco or Fish Tales Market & Eatery (because Florida Keys travelers can never have enough seafood), then make your way to Crane Point Hammock, a museum and nature park where you can learn even more about the wildlife and ecosystem of the Keys.
For dinner, we highly recommend Castaway Waterfront Restaurant & Sushi Bar, not just for its seafood, but also for its 52 beers on tap. Continue the evening with more drinks at one of the local bars, like JJ’s Dog House, Overseas Pub & Grill or the Brass Monkey.
Sunday: Sightseeing in Key West
Key West is arguably the most sightseeing-driven of the keys, especially for history buffs. But never go museum-hopping on an empty stomach.
Eat at one of the French breakfast spots for a departure from classic American breakfasts of bacon and eggs. Banana Café has a sunny decor scheme, creative combos and a breezy roof deck, while La Crêperie French Café Key West is traditional in the best way, right down to the Brittany-style buckwheat galettes.
Then, meet some of Key West’s famous former residents via their historic homes: Visit the Hemingway Home & Museum and Harry S. Truman Little White House. You can also take in historic Mallory Square, snap a photo at the buoy marking the southernmost point of the continental U.S. or delight in the butterflies at the Key West Butterfly & Nature Conservatory.
Lunch should be brief because there’s a treat in store for you this afternoon: One of the least-visited national parks in the country is located 70 miles off Key West.
Pick up a cubano sandwich and a café con leche at 5 Brothers, then walk over to the ferry terminal and catch a boat to Dry Tortugas National Park, a 100-square-mile area with seven small islands, one of which is home to the 19th-century Fort Jefferson. If you’re not waterlogged yet, you can dive back into the sea for some stellar snorkeling or diving. (Don’t miss the Windjammer Shipwreck!)
When you head back to Key West, finish your trip with the Asian-inflected tasting menu at stylish, upscale Little Pearl, then it’s time to enjoy the legendary nightlife on Duval Street — Flying Monkeys Saloon is a favorite — to conclude your Florida Keys odyssey.
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