The most traveled and visible street in Key West is only the beginning, the surface, of what the town has to offer. Ask the locals about their favorite spots, stroll through quiet neighborhoods or down alleyways off Duval and you’ll begin to dive deeper into the quieter, more diverse and less readily apparent offerings. Here are eight spots that you might not see at first glance.
¦ Bobby’s Monkey Bar (900 Simonton St.; (305) 294-2655) This locals’ dive has nightly karaoke that often includes more than your typical drunken yodeling. Drag queens on their night off and former Broadway performers have been known to carry a tune here as well.
¦ Leather Master of Key West (418 Applerouth Lane; (305) 292-5051) The guys who own this place hand-make many of the sexy leather products right here at their workshop. In business for more than 30 years, its selection of masks, headdress, costumes and numerous accessories caters to any preference. The staff will also help you with makeup tips.
¦ 2 Cents Restaurant & Pub (416 Applerouth Lane; (305) 414-8626); 2centskw.com) is right behind Leather Master and just off Duval, but it’s hard to find with little signage and inside feels like a world away. The nautical-themed bar is warm and homey. Small and large plates include items such as roasted bone marrow and yellowtail snapper and knowledgeable bartenders mix up craft cocktails such as Curse Like a Saler with gin, dolin blanc, agave, basil, mint and grapefruit. F***in brilliant!
¦ Cornish Memorial African Methodist Episcopal Zion Church, 702 Whitehead St. Established in 1864 by former slaves Sandy Cornish and his wife, Lillah, who escaped to Key West and later became some of the wealthiest residents of Key West. The current building was built in 1894.
¦ The Rev. Long organized the Bethel AME Church in 1870 at 712 Duval St. It was destroyed by a fire in 1922 and the congregation then moved to the corner of Thomas Street and Truman Avenue. The building features masonry walls, twin towers in front and pointed-arch windows reminiscent of the Gothic Revival Style.
¦ Key West Island Bookstore (513 Fleming St.; Keywestislandbooks.com; (305) 294-2904). This decades-old boutique bookstore offers a surprisingly varied wealth of current and used titles, from best-sellers to rare titles. Often open late, it’s an inviting place to browse among the crowded stacks.
¦ Cuban Coffee Queen (284 Margaret St.; (305) 292-4747; cubancoffeequeen.com). The strong Cuban coffee at this hole in the wall is also rich in Key West heritage. A Café Con Leche paired with a classic Cuban sandwich or some Havana rice and beans will keep you going long into a Key West night.
¦ Better than Sex (926 Simonton St.; (305) 296-8102; betterthansexkeywest.com). A great place for couples, swing by this dessert-only, adults-only restaurant late in the evening. Indulge your senses with chocolate-dipped wineglasses and cheeky, homemade desserts and beverages
such as an Ephemere Apple Spiced Ale in a tall beer glass with a signature caramel rim-job. Lick it good.
¦ Deuces “Off the Hook” Grill (728 Simonton St.; (305) 414-8428; offthehookkeywest.com). Tucked into a quiet neighborhood, Off the Hook serves breakfast and lunch, but the creative and well-executed dinner menu featuring fresh seafood is especially enticing. Grouper in a French bouillabaisse broth, fish and chips featuring mahi-mahi, and slow-roasted Jamaican jerk chicken thighs are recommended.
¦ La Rubia Fine Hats (510 Fleming St.; (305) 296-6059, larubiakeywest.com). The Florida Keys’ only importer of authentic Panama hats. The owners developed this boutique to carry on the centuries-old tradition of hand-weaving hats, which come from Ecuador. ¦