Insider’s Guide

How to enjoy Key West like a "conch."

Above: Key West is a place to slow down, unplug and enjoy the surroundings. “Look for the amazing glow that bathes everything in gold when the sun is setting,” Scott Valbert suggests.

Key West Glow
Couple reveals how to enjoy the Florida island like a ‘conch.’

Writer: Lisa Lavia Ryan

Scott Valbert and John Carstensen’s first taste of Key West didn’t exactly portend they’d end up living there one day—but it did leave the couple with a good feeling about the historic tourist destination.

“We were on a cruise and Key West was one of the stops, and we walked off the ship and into a bar with two-for-one beers and stayed there all night,” Valbert says with a laugh. “I remember we smiled at each other a lot and kept saying, ‘Oh, isn’t this great?’ But we never thought for a moment that we’d be moving there.”

That’s exactly what happened in late 2009, though, after a particularly harsh Iowa winter wore them down and an unforeseen job opportunity came up. Until they moved back to Des Moines in early 2012, Valbert, now a communications executive with Bankers Trust Co., and Carstensen, an internal medicine physician with UnityPoint Health, explored their new town, learning about the island as they hosted 65 houseguests and led them to typical tourist destinations as well as those off the beaten path. The result is their curated list of recommendations for enjoying Key West like a conch—the curious moniker by which native Key West dwellers refer to themselves.

The two still love Key West and visit at least twice a year. Their primary piece of advice for others who plan to travel there: “Slow down, get off your phone and look around,” Valbert says. “Look for the amazing glow that bathes everything in gold when the sun is setting. I remember a gift someone gave me once—a plaque or something—and it said, ‘If you’re lucky enough to live on an island, you’re lucky enough.’ I think of that, and in my mind I see that glow.”

Explore Old Town on two wheels. “Rent bikes immediately,” Valbert suggests.

The island’s historic district—once home to such notables as Ernest Hemingway, Tennessee Williams and President Harry Truman—teems with an architectural richness, Valbert says. “There are over 3,000 historic wooden homes, and the unique thing is you’ll see a little cigar maker’s cottage right next to a shipwrecker’s mansion. You’ll find many cool little neighborhoods to explore.”

Immerse yourself in art and literature—and say hi to Judy Blume. The best-selling author and National Book Foundation medalist owns, and often works at, Books & Books, part of a nonprofit arts organization called the Studios of Key West. There, you’ll also find art galleries, lecture halls, workshops and other ventures that contribute to the island’s robust fine-arts culture.

If you’re in the market for some additional art to take home, Valbert and Carstensen recommend Art@830, which sells everything from folk art to fine oils and watercolors; Gallery on Greene, which showcases award-winning artists; and Gingerbread Square Gallery, which offers smaller pieces, including many by local artists.

Take your appetite. “There’s no way we could have eaten everywhere in two years,” Valbert says, “but we tried!” A few favorites: Santiago’s Bodega, featuring small plates and sangria; Azur, a brunch spot known for its seafood; Old Town Bakery, famous for ham-and-cheese croissants, sticky pecan rolls and an unbelievable backstory (“Go there and ask!” Valbert says); and Moondog Cafe, which serves wood-fire pizzas and casual fare. Key West Cakes is another favorite sweet-tooth satisfier.

Other can’t-miss restaurants: Sandy’s Cafe, a Cuban sandwich shop housed in a launderette; Seven Fish, renowned for its seafood; and Cafe Marquesa, “the island’s only white-linen-table-cloth place,” Valbert says.


Shop, of course. Valbert and Carstensen are fond of the island’s “fun little stores,” beginning with the cluster of boutiques along Duval Street, the island’s 1.25-mile-long main drag. Off Duval, though, you’ll find some of their favorites, including Salt Gallery, which offers art, jewelry, pottery, wine, books, wild local honey and handcrafted sea salts. For authentic Key West flavor, stop by Rodriguez Cigar Factory, where you can immerse yourself in cigar history, sample the wares and roll your own.

Explore after dark. Key West is known for its nightlife, and Valbert and Carstensen’s list includes options ranging from loud to laid-back. Start with La Te Da on Duval Street, a bar, restaurant and cabaret known for its female impersonators. The Saint, another favorite, features “really hip furniture and lots of black and white,” Valbert says. “And the balcony bar area looks over Duval. Going there is something most people do at least once.” Other favorite nightspots: Nine One Five, Green Parrot, Irish Kevin’s, Sloppy Joe’s, Louie’s Backyard and Margaritaville.

Don’t miss the sunset celebration at Mallory Square, Valbert says. “Everyone gathers where the cruise ships come in to watch the sunset,” he explains. “Words can’t do justice to how beautiful the sunsets are there.”

Get out of town. Take a ferry to Sunset Key, an exclusive private island (but make sure to arrange your stay first; you can’t just show up) to see a spectacular sunset from a beachfront hotel. For something a little less exclusive, book a sunset cruise, either on a party boat or on a quiet sailboat.

If you’re in the mood for a day trip, head to Dry Tortugas National Park, about 50 miles from the Keys, for a dose of history. You’ll see Fort Jefferson, a massive coastal fortress that’s the largest brick masonry structure in the Americas. Other options for outdoor adventures: Rent some personal watercraft or paddleboards, go parasailing, or visit the Key West Butterfly and Nature Conservancy.

Locally owned boutiques offer one-of-a-kind goods.
Now a U.S. National Historic Landmark, this house was Ernest Hemingway’s home from 1931 to 1939.
Covering 16 acres, Fort Jefferson is an unfinished coastal fortress.

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