By day, folks on bicycles lazily push past roaming roosters; by night, watering holes reverberate with raucous good times. Welcome to Key West’s Old Town, where the rowdy meets the refined.

By Cricket Desmarais | Photos © Rob O’Neal

From above, we must’ve looked like fish ourselves. Eyes glassy, heads hung back, and mouths agape as my visiting friends and I hurled quarters up to the sky. Several years ago, we had stood in front of Key West’s infamous Captain Tony’s Saloon, a smoky Old Town bar whose decor includes barstools painted with the names of famous patrons, including Ernest Hemingway, Truman Capote, even John F. Kennedy. Our hopes were that the great stuffed grouper pitching out from the side of the building would swallow up our “catch” and return our rum-imbibed wishes.

A silly tradition at best, it’s a side of the Old Town Key West experience I love to share – a loose vibe and an anything-can-happen attitude. But as a 15-year local now, I know that there are actually two sides to this district, which covers nearly a square mile of the westernmost portion of the island. Duval Street may be the most obvious of Old Town’s offerings, thumping with an eclectic mix of bars, boutiques, and eateries, but lateral streets like Greene, Caroline, Eaton, Southard, and Fleming bisect on either side and offer more charming, antiquated perspectives.

Which brings me back to Captain Tony’s Saloon, a prime example of the edgy and daring. As Florida’s oldest bar (according to the sign on the storefront), it’s where Jimmy Buffet got his start playing in trade for six-packs. I once interviewed the owner, the late Captain Tony Tarracino (he passed in 2008). Then age 90 and the father of 13 kids, Captain Tony was, at first, somewhat crude and irreverent, meeting me in his house slippers and a cigarette in his mouth. Visitors were undeniably drawn to him, roaring with laughter after hearing one of his famous stories – like how he hitchhiked to Key West in 1948, how he ran for mayor five times (he was finally elected in 1989), and how he had married at least three times. His wild flair for dramatics could be intriguing to visitors – it certainly made him one of the island’s most beloved citizens.

But, like I said, Old Town and a Florida Keys vacation aren’t all rum and feathers. Mornings in Old Town are exceptional. There is a sense of calm that pervades in the earlier hours before the hustle of business begins. Frangipani, bougainvillea, orchids, and a variety of palms line those aforementioned side streets that are dominated with a mixture of architecture styles – a mishmash of Bahamian “conch homes,” Victorian mansions, and simple cottages reminiscent of New England. It’s relaxing, reserved, and even a bit dignified.

The neighborhood is also quite the shopping mecca. My personal favorite is Local Color, outside of the Bahama Village on Margaret Street. The store is stocked with breezy linens, unusual gems set in handcrafted silver, and a full line of my favorite yoga wear. And while it is based in the part of the district that was famous for a past when pirates, wreckers, bootleggers, and fishermen once plundered, the owners, Lilian and Jack Anderson, are glamorous in a John and Jackie Kennedy way – sailing here aboard their own sloop three decades ago from France. They’re hardly anything like Captain Tony.

But I think I developed something of a soft spot for him. During that interview, he offered this piece of info: “My secret is – I’m confessing now – if I can make people laugh, if I can make them smile, if I can make them feel good about themselves, I don’t want nothing [in return].” Edgy, sometimes crude, yet charming. Kind of like Old Town itself.

Where to Stay Margaritaville Key West Resort & Marina | Sunset Key Cottages