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 8 spots that you might not see at first glance.
Bobby’s Monkey Bar (900 Simonton Street; 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, their selection of masks, headdress, costumes and numerous accessories cater to any preference. The staff will also help you with makeup tips.
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!
Bethel A.M.E. Church (223 Truman Avenue; 305-294-9951). Feeling guilty after too much drinking? Try a service at this African Methodist Episcopal Church or just stop by. It was established in part by a former slave, Sandy Cornish, who escaped to Key West and became a successful and wealthy farmer.
Key West Island Bookstore (513 Fleming Street; 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 Street; 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 Street; 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 wine glasses 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 Street; 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 along with dark chocolate covered banana bread for dessert. The Duck BLT pizza is also delicious. It’s a small space. n