Cigar Aficionado

The Florida Keys long ago evolved from a sleepy stretch of islands connected by the Overseas Highway into a magnet for snowbirds, weekend fishermen and cruise-ship tourists. As a result, those who go seeking the kind of total escape that Ernest Hemingway once found there—the writer spent much of the 1930s in Key West—are often disappointed. Hawks Cay is the exception.

Turning off U.S. 1 and onto the small bridge leading to Hawks Cay, my wife and I were pleased to discover that the resort is on an island all its own, one of five constituting the community of Duck Key. (The other four islands are strictly residential.) First designed by the celebrated architect Morris Lapidus­, Hawks Cay opened as the Indies Inn in 1960. Back then, bamboo accents and native masks were the defining motif.

Now owned by Northview Hotel Group, the 60-acre resort—which boasts more than 400 hotel rooms and villas—underwent a $35 million renovation in 2008 that upped the luxury quotient without sacrificing the tropical vibe. It still feels like an island retreat, albeit one with such modern amenities as marble showers, stainless-steel appliances, state-of-the-art fitness equipment and concierge service.

Our room was in the main building, conveniently overlooking the Tranquility Pool, a no-splash, adults-only zone perfect for lounging. (The property includes three other pools, and families with children tend to gravitate to the Lagoon, a man-made beach and saltwater oasis on the edge of the Atlantic Ocean, where kids can kayak and marvel at the small fish that wander in.)

Even while Hawks Cay offers almost every activity imaginable—fishing tennis, offshore, parasailing and more—my wife and I opted for a quieter, more romantic getaway. It included his-and-hers massages at the resort’s award-winning Calm Waters Spa, followed by a date with the dolphins at Dolphin Connection, where visitors can get right into the water with the animals and their handlers.

We wrapped up our two-day sojourn with cocktails and dinner at Alma, the resort’s signature restaurant. Sleek and upscale, Alma wouldn’t seem out of place in a chic nightlife district. A delectable dinner of pan-seared scallops, wagyu churrasco steak and the fresh catch of the day left no room for dessert nor regrets.

It was the kind of meal that begs to be topped off with a fine cigar. Here again, Hawks Cay accommodates. Not only does Alma offer a nice selection of sticks, but just beyond its doors is the resort’s famed fire pit, which is just what it sounds like. Around a roaring flame, under the night sky, guests can enjoy an after-dinner drink, live music and, if they so choose, a smoke.

“We have no brand affiliation, no standard other than Hawks Cay,” says managing director Sheldon Suga, explaining the resort’s independent, cigar-friendly philosophy. “With this much area, why shouldn’t people be allowed to smoke?” Somewhere, Hemingway’s ghost is smiling.