Road-Tripping From Miami to Key West: The 5 Best Stops Along the Way

Our pick of off-route diversions, including one of the best hotels in the country

April 14, 2023 7:00 am
Highway going across small strip of land on top of large blue body of water.
Sail, fish or stay in a fancy hotel at one of these five go-to places.
Andy Newman

The drive along Route 1 from Miami to Key West is an engineering marvel, a test of endurance and incomparably beautiful. It’s also made infinitely better by breaks, whether for top-notch sailing excursions or a stay at one of the country’s top (and most expensive) hotels. Whether you’re looking to cos-play Key Largo, sleep with the fishes or just book into a very fancy hotel, here’s how to break up the drive with five brilliant stops along the way.

View of a pink and orange sunset over the water through palm tree leaves.
Stop in Key Largo for the beachfront Caribbean Club bar, or sleep in an undersea lodge with the fishes.
Bob Krist/Florida Keys News Bure

Key Largo

“The First Key” is still famous for the Bogart and Bacall thriller Key Largo, making it worth a stop to check out the beachfront Caribbean Club bar, where parts of that classic were filmed. Open since 1938, the club has live music all weekend and pours their unique cocktail, the Key Lime Pie Rum Punch. Have a few of those and you’ll want to stay the night. 

For a distinctly odd sleeping situation, book into Jules’ Undersea Lodge, where you’ll literally sleep with the fishes inside an underwater bedroom reached by scuba diving down. (This is also where Dr. Joseph Dituri is trying to live underwater for 100 days.) You don’t need to be a certified diver to do the dive, and they even serve you a pizza feast for dinner under the sea.

And if Bogart is your favorite Hollywood hero, the actual “African Queen” steamboat used in the Bogart-Hepburn classic film is anchored in Key Largo’s Marina del Mar and offers 1.5-hour trips through the Port Largo Canals and out into the Atlantic Ocean, without any of the trials and tribulations the actors experienced while aboard in Uganda and the Congo. Check out the John Pennekamp Coral Reef State Park before you roll on south, as it is the first underwater preserve in the United States and also boasts beautiful nature trails and pretty beaches.

Highway going across small strip of land on top of large blue body of water.
Islamorada is known as a paradise for anglers.
Andy Newman


Hang out in Islamorada for a day or two if fishing floats your boat, as this “Village of Islands” made up of Plantation, Windley, Upper and Lower Matecumbe keys is known as a paradise for anglers. Catch a big-money tournament or go out yourself (you can rent everything from boat and guide to equipment here) to try for sailfish, marlin, tuna, tarpon, bonefish and more.

Classic spots like the Green Turtle Inn will cook your catch for you — or simply book into the luxe Cheeca Lodge and Spa, where an oceanfront suite leads to both boat charters and fishing off their 525-foot pier. Their posh (and award-winning) Atlantic’s Edge restaurant will cook up whatever you catch — fried, grilled or blackened.

Consider strapping on scuba diving tanks here, as there are numerous reefs nearby, as well as the Eagle, a deep wreck for experienced divers to explore at 70 to 100 feet, and a circa-1733 Spanish galleon that sits in the San Pedro Underwater Archaeological Preserve at about 15 feet, giving a view to snorkelers, too.

InsideCart: What Our Editors Bought in April
Including sunglasses, cookbooks and CBN gummies
Umbrella and lounge chairs lined up along a lagoon waterfront at sunset.
Visit Hawks Cay Resort, a Caribbean-style resort with private villas, dolphin encounters and water sports.

Duck Key

On Duck Key, a bit over halfway to Key West from Miami, discover Hawks Cay Resort, a place that may make you decide to just stop right there. Originally built in 1951 as the Indies Inn (about the same time Duck Key was connected to Route 1 via a wooden bridge), today the resort has weathered hurricanes and come back as a Caribbean-style resort with everything from private villas to dolphin encounters, water sports and fishing adventures. And pickleball, of course, complete with clinics to teach the finer points of the sport that has swept the nation. Hawks Cay Resort is pretty much the only game in town on bucolic Duck Key, so rent a golf cart for your stay and you can putter around the key to discover secluded spots with great views, gorgeous flowers and a seriously laid-back vibe.

A deer stopped in a field of grass and flowers.
Big Pine Key is a go-to spot for camping, RVing or renting an Airstream “hotel room.”
Rob O’Neal/Florida Keys News Bureau

Big Pine Key

Only 30 minutes from Key West, Big Pine Key has a completely different feel. Known for the natural beauty that makes up most of this island, it’s been a protected place for decades, with Big Pine and the nearby “Lower Keys” like Looe, Little, Middle and Big Torch keys serving as the home for two national wildlife refuges and a marine sanctuary. This is the place to be if camping, RVing or renting an Airstream “hotel room” is your jam. Here’s the spot known for its dark skies, where getting away from the big city (including Key West) means views of the Milky Way instead of neon lights. Big Pine Key Resort is one of the many camping/RVing places with bathrooms, hookups, ice and the other things you’ll need for having a camping adventure in the Keys.

A view from an airplane of the Florida Keys, overlooking a body of land and the ocean.
Relax at the Little Palm Island Resort and Spa for a remote, off-the-grid getaway.
Laurence Norah/Florida Keys News Bureau

Little Torch Key and Little Palm Island Resort

About as far from camping as you can get is the ultimate stop on our drive through the Keys. That’s Little Palm Island Resort and Spa, a tiny island at the outer end of Big Pine Key, but only accessible by boat or seaplane (catch those on Little Torch Key). That’s the place with a very big nightly price tag (think $3K) that allows adults only to escape from everything (no phones, no TVs). They are doing something right, having been repeatedly voted one of the world’s best by both Travel & Leisure and Conde Nast Traveler readers and many others. Getaway luxury, especially for couples, awaits at this little gem of the Florida Keys.


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