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

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.

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.

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.

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.

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.

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.

Get planning your next trip to Florida Keys at fla-keys.com