Key West has a richness that becomes more apparent with each new exploration of the island. Taking the time to experience it is like savoring a plate of Cuban food — allowing yourself the chance to appreciate each dish’s individual flavors, textures and contrasts.
The places listed here are renowned for their atmosphere and attractions. Most likely, you won’t discover them by accident — yet seeking them out will add to your enjoyment of Key West whether your stay lasts a few days, a season, or a lifetime.
For example, if you’re looking for a great local bar, stop by the Schooner Wharf (www.schoonerwharf.com) at 202 William St. Located on the waterfront in the Historic Seaport, it’s the kind of funky open-air place where you can bring your dog, your girlfriend and half a dozen fishing buddies — and everyone will have a good time.
Schooner Wharf’s owners pay special attention to finding high-quality bands to grace the small stage. Despite their talent, it’s singer-songwriter Michael McCloud whose music defines the bar. Generally playing from noon to 5 p.m., McCloud is best when performing his original tunes spiced with island attitude and rueful humor.
About a block from the Schooner Wharf, at the colorful Kermit’s Key West Key Lime Shoppe (www.keylimeshop.com) at 200A Elizabeth St., you’ll find unique Keys gifts and decadent treats. This emporium is the home of everything Key lime — from bottles of the island’s signature Key lime juice to Key lime sauces, soap, candles, dressings, shampoo, jellies and more.
The biggest attractions, though, are slices of traditional Key lime pie and indescribably good chocolate-covered frozen Key lime pie on a stick — and exuberant shop owner Kermit Carpenter, who can often be seen standing outside the shop in his chef’s whites preparing to “throw” a Key lime pie at unwary passersby.
Across the island lies an upscale cocktail hideaway in a picturesque Key West setting: the Afterdeck at Louie’s Backyard (www.louiesbackyard.com), on the edge of the Atlantic Ocean at 700 Waddell Ave. Beloved by Key West literary legends, visiting celebrities, world-class fishing guides and savvy locals, the Afterdeck is a place to take someone special — whether the love of your life, a treasured friend or a visiting relative you want to impress.
One of Key West’s finest gourmet restaurants, Louie’s Backyard itself occupies a restored Victorian house with dining inside and on tiered decks leading down to the Afterdeck and the water. After dark, lights spill from the house and the decks to illuminate the bar, the stars above look practically close enough to touch, and the Atlantic unrolls seemingly halfway to Cuba.
Speaking of dining, eating Cuban food in Key West — whether you’re a first-time visitor or an aspiring local — is a necessity. It’s probably mandated in the city charter somewhere (and if it isn’t, it should be). There’s an ongoing controversy about which is the island’s best Cuban restaurant, but don’t get drawn into it. The clear winner is El Siboney (www.elsiboneyrestaurant.com), an out-of-the-way spot tucked into a quiet residential neighborhood.
Located at the corner of Catherine and Margaret streets, El Siboney is an inexpensive family-friendly eatery that serves some of the best roast chicken anywhere (and the largest portions). Accompanied by black beans and yellow rice, Cuban bread and sweet plantains, the perfectly-seasoned chicken is so tender it practically falls off the bone.
Of course El Siboney also offers other Cuban specialties: traditional ropa vieja and picadillo, savory roast pork and dishes marinated in a garlicky sauce called mojo criollo.
From its Cuban restaurants to waterfront watering holes, Key West is just waiting to be explored. Use the suggestions here as a beginning, and start compiling your own list of favorite places.