There’s a reason Jimmy Buffett was more than happy wasting away in Margaritaville for decades, content chasing that elusive shaker of salt from bar to bar in Key West. There’s a calm to be found in the sun-bleached beaches and laidback watering holes scattered among the seven small islands that form Florida’s southernmost city.

Buffett eventually capitalized on that beach bum vibe, founding what would become a chain of Margaritavilles and cashing in big on selling the simple life. But vestiges of the Key West that so entranced the singer when he arrived in the early ’70s remain rooted in the sand on Stock Island, an artsy enclave that welcomed its first hotel when the Oceans Edge Key West Hotel & Marina opened in January. Named for its location at the edge of the Atlantic and the Gulf of Mexico—a setting that affords ocean views to each of its 175 luxurious rooms—the sprawling 20-acre resort is the largest in Key West.

There are six swimming pools spaced out over the property, but the bathing is even better in the turquoise waters beyond the marina’s docks. Book a stand-up paddle boarding excursion with the watersports crew at the hotel and a pro will take you out into the Keys’ winding, peaceful inlets, where you can practice feats of nautical athleticism with a view of the great blue herons that graze serenely nearby. (Wildlife enthusiasts should book an Eco Paddle to meet some of the other fauna that call the Keys home.) After all that exercise, you can reward yourself with a cold beer from the BYOB cooler on the boat. Pro tip: The brave and/or very thirsty might ask the tanned and muscled deckhand about the “scuba funnel.” It’s like a beer bong. Through a snorkel mask.

Hogfish Tacos

You can regain your land legs at the hotel’s Yellowfin Bar & Grill, a serviceable upscale beach bar serving seafood staples like conch chowder and crabcake sandwiches. Those in search of a taste of old Key West, however, should wander outside the hotel’s impeccably manicured grounds, where there’s many a cheeseburger—or hogfish sandwich—to eat in paradise. The latter can be found at Hogfish Bar & Grill in Safe Harbor Marina. Named for the native fish that’s tastier than it is pretty (Google Image it after you eat it), the Hogfish boasts a no-shoes-no-shirt-no-problem vibe (but wear shoes just in case). It’s owned by a genial, Buffett-like local who makes the rounds, greeting patrons that include one of his most faithful customers—a scruffy street cat who’s been visiting the Hogfish for 16 years, usually sticking around after a meal to catnap in the sun.

After a late, leisurely lunch of hogfish tacos or conch fritters, visit COAST, a charmingly ramshackle artist collective and creative space housing painters, woodworkers, muralists and other artisans who work in “studios” that include a hollowed-out old VW bus. COAST was founded by Boston expat Billy Kearins, a former Gloucester boat-builder who now sells his hand-carved wooden skateboards along with flat-brimmed hats and screen-printed tees out of a small shop in one of COAST’s many nooks. He also books bands to play a makeshift stage where locals and out-of-towners alike have gathered for recent appearances by the likes of G. Love. Peruse the collective’s wares as the sun dips below the horizon, painting the sky with one of Key West’s vivid sunsets. Then head out on the town.

On the island of Key West, there are plenty of spring break-sanctioned bars—including the original Margaritaville—along famously rowdy Duval Street. Skip most of them, with the exception of the Other Side, located inside a house that was once home to Key West’s first native-born physician and named to the National Register of Historic Places in 1973, where you can sip on expertly crafted cocktails among discerning locals. Less discerning residents can be found at the Green Parrot, a lively “locals only” dive where perma-tanned regulars (and the errant frat boy who wandered too far off Duval Street) dance with abandon to the live bands who take the bar’s stage nightly.

Hotel Sunset

Another evening, you might skip the bustling bar scene (or pregame it) on a sunset sail aboard the Schooner Hindu. Another New England transplant, the 90-year-old ship was built in Boothbay, Maine, and spends its summers cruising Provincetown. In Key West, the Hindu offers chartered evening cruises, where guests are treated to both breathtaking sunsets (the lucky sunset peeper will experience Key West’s rare but famous “green flash”) and an assortment of cold craft beers, cider and red, white and sparkling wines. Cheese platters are proffered by the charming Lt. John, the Hindu’s preteen deckhand, who has the face of a cherub and the gravitas of a master sommelier. Don’t be too shy to take a picture of yourself “steering” the ship. It’s practically mandatory.

Wherever your Key West adventures take you, be sure to spend a few quiet moments taking in the view from your hotel room balcony with a margarita in hand. It would be a shame to waste it.

Traveler’s Checks      

– Out on the town with the munchies? Sidle up to the grilled cheese stand in locals-approved upscale dive Mary Ellen’s for gooey, crusty sandwiches and hand-cut fries.
– For a more refined dining experience, visit Thirsty Mermaid, a cozy but sleek seafood boîte boasting an excellent raw bar and an extensive wine list.

COAST; The Green Parrot; Hogfish Bar & Grill; Mary Ellen’s; Oceans Edge Key West Hotel & Marina; The Other Side; Schooner Hindu; Thirsty Mermaid

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