Key Largo to Key West: Island Hopping Like a Local in the Florida Keys

Kayaking is just one of the many ways to explore the tranquil waters of Florida Keys
Kayaking is just one of the many ways to explore the tranquil waters of Florida Keys | © Corey Rich / Getty Images
Jay Gentile

If you think the Florida Keys consist of little more than bleary-eyed Jimmy Buffett bars and fanny-pack-wielding crowds lining up for another helping of key lime pie, you might need a gentle reminder that Key West is not all there is to see here. With 1,700 islands, and endless opportunities for off-the-beaten-path exploration, you’d be wise to take a little extra time to see what else is out there on your next trip down the Overseas Highway. From lesser-known islands and beaches to friendly local bars and restaurants, here’s how to island-hop the Keys like a local.

Take a step back in time at the Caribbean Club

As the first island on the tourist trail from Miami, Key Largo often gets overlooked by busy travelers who can’t wait to get stuck in traffic outside Key West. But locals know Key Largo as an excellent setting in which to escape the tourist crowds and where better to do that than at legendary local hangouts such as the Caribbean Club. The oldest bar in the Upper Keys and one of the last holdouts of Old Key Largo, it can also be counted on for live music and killer sunsets. Just don’t spend all your time here, as the area also boasts some of the finest snorkeling in the Keys and you can explore areas like the John Pennekamp Coral Reef State Park.

Left: John Pennekamp Coral Reef State Park is the first underwater park in the US. Right: swing by the Caribbean Club for chilled vibes and live music

Eat like a local on Stock Island

Traditionally home to a more working-class scene, populated by local fishermen and tourism workers, Stock Island may be just over the highway from Key West, but it has a more down-to-earth feel. While developing quickly into a tourist attraction, it is still populated with local gems such as El Siboney, hidden in a cool residential area and a must-visit for fans of authentic Cuban cuisine. The Hogfish Bar & Grill is another fine local institution famous for its decadent hogfish sandwich, made with Cuban bread.

If you’re after seafood straight from the boat, with harbour views to boot, hit up Hogfish Bar & Grill

Fish like a local in the backcountry

The Keys – and especially the area around Islamorada – are home to some of the world’s finest sport fishing spots, and they are also home to groups of mangrove islands that local fishermen call the “backcountry”. Resembling a sort of back alley that can be found off the Overseas Highway tourist trail, this fishermen’s oasis is best explored with help from a local guide like Captain Rick Smith of Angling Adventures. You can also explore this peaceful area by kayak or canoe.

Left: the waters of Islamorada are home to some of the best fishing spots in the world. Right: kayaking or canoeing is one of the more peaceful ways to explore waters of Islamorada

Hit Bahia Honda and Sombrero Beach

Many of the beaches in the Florida Keys aren’t known for their scenic beauty, yet there are still a few gems to be found away from the crowds. Bahia Honda, in the Bahia Honda State Park between Marathon and Big Pine Key, is a truly special place – you can even camp here and spend the night in a tent or cabin. Be sure to also check out Sombrero Beach on Marathon Key; it is populated year-round and has a small-town feel, a far cry from the endless parade of cruise ships parking up on the shores of Key West.

Sombrero Beach is so quiet that, from April to October, loggerhead turtles come here to lay their eggs

Drink like a local at No Name Pub

While the tourist throngs pack Duval Street for yet another night of Bourbon Street-style debauchery, those looking for a more low-key experience in a lesser trafficked watering hole would be wise to check out the No Name Pub on Big Pine Key. With dollar bills plastered on the ceiling and (surprisingly) some of the best bar-room pizza in the state, it’s the perfect gateway to Big Pine Key itself, an oft-overlooked natural wonderland teeming with greenery and miniature key deer – and very few tourists.

This no-frills bar-restaurant is a top place to meet like-minded travelers

Get off Duval Street

Yes, Key West is crowded. Yes, Duval Street is insane. But just a few steps off the main drag you can find an entirely different experience. Instead of elbowing out tourists with selfie sticks for a snapshot in front of the southernmost point of the Continental USA Buoy, wander to the historic seaport district to find 90 Miles to Cuba, an oddball art gallery in a delightfully weathered shack. Check out the vibrant outdoor scene at the colorful Bahama Village Market and take in the nightly (touristy but still fun) Sunset Celebrations Arts Festival at Mallory Square. The Hemingway Museum can wait.

The Southernmost Point Buoy in Key West

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