Best Cuban: Off the beaten path, this no-frills restaurant serves up generous portions of the best Cuban food on the island at reasonable prices. Mid-day the place is usually bustling with the local lunch break crowd mixed with a healthy dose of visitors in-the-know. The hodge-podge décor includes diner-style tables covered in a red pepper-patterned plastic table cloth, photos of Cuba and a life-size wooden Indian--a nod to the namesake Cuban tribe. A basket of fresh Cuban bread arrives at your table first with thick fluffy slices slathered in butter. Pair it with a pitcher of the house sangria. Follow up with your order of entrees like tender roast pork or perfectly-spiced picadillo (a ground beef entrée). The food comes quickly accompanied by a plate overflowing with fried plantains so sweet you may not even want dessert. Of course, you'll have a dessert. The rich creamy flan is too yummy to ignore.
Best Pizza: Hidden down a small walkway off Duval, you'll discover the enchanting garden of Onlywood Pizzeria Trattoria. Owners Davide Cremascoli and Alessandro Piazzo, who grew up in a small village in Napoletana Italy, are devoted to bringing you the most authentic Italian pizza possible. If you sit inside, you can watch your pizza being made from scratch and baked in the 2-ton wood-fired oven imported from Italy. With great attention to detail, they only use oak wood to maintain the proper temperature inside the oven. Their mozzarella is made fresh daily, and superfine flour makes for a very light thin crust. Pair your meal with a glass (or carafe) of their refreshing homemade sangria made with fresh mint.
Best Seafood: For a taste of a true local's joint just five minutes away from Old Town, follow the signs to the Hogfish Bar and Grill, located in Safe Harbor Marina on Stock Island. Try anything that's made with their namesake specialty like the "Killer" Hogfish Sandwich, which is smothered in Swiss cheese, onions and mushrooms on a fresh Cuban roll. The Hogfish Fingers or Fried Hogfish Tacos are also favorites or dig into a plate of "Peel 'n' Eat" Key West pink shrimp. All dishes call for an ice cold beer. This open-air, casual restaurant is a diamond-in-the-rough with live entertainment and a popular happy hour. The owners try to maintain that Old Key West vibe, and views of Key West's last working waterfront are a bonus.
Best Desserts: One of the most talked about culinary experiences in the Florida Keys, Better Than Sex dessert cafe wows with their sinful concoctions like Cookie Nookie Pie and Between My Red Velvet Sheets Cheesecake. Pair with their Choco-Cab, cabernet served in a chocolate-rimmed wine glass. It's so tasty you'll be licking the rim. The Kiss me, Carolyn, is a dessert in itself with Ayala champagne in a soft caramel dipped wine glass rimmed in bruleed raw sugar. Dark intimate lighting is offset by menus that light up and flashlights on the table. This romantic after-dinner stop certainly sets the mood for the rest of your evening.
Best Sunset: For upscale dining with a stellar view of the sunset, head to Hot Tin Roof at Ocean Key Resort and Spa located just off Mallory Square. You can dine alfresco on their patio with the sounds of Jimmy Buffett classics wafting up from the band on Sunset Pier, as boats ply the aquamarine waters in the harbor. The Pan-Latin menu offers small and large plates, so you can design your own meal, whether shared tapas-style or traditional entrees. Dishes like the Key lime fish ceviche, paella and caramelized grouper capitalize on the fresh local seafood. Finish with their delicious Key lime pie in a cashew graham cracker crust. You'll love the dusting of cinnamon in the shape of a palm tree on the plate. The understated elegance makes this a perfect spot for romantic couples. Note that the requested attire is resort casual. Average dinner prices range from $10 for small plates to $35 for entrees.
Best Budget: This seafood shack may look like it's barely standing, but the food certainly holds its own. What began as a makeshift food truck in the 70s, opened by local legend Buddy Owen, has become a staple in Key West. The fresh fish sandwiches are simple, yet the best in town. Bobby Flay and his Food Network camera crew even paid a visit for the cracked conch sandwich--tiny strips of fried conch stuffed between fresh Cuban bread and shot with Key Lime mayo. Conch fritters, salads, burgers, and hot dogs are equally tasty, and the anything-goes atmosphere sums up the entire town. The restaurant stays open until 9:30 p.m. on most nights (they'll close early if they aren't busy), and on Friday nights, you can enjoy an all-out musical jam session.
Best Brunch: In Key West, this restaurant needs little introduction. The private courtyard (once home to Hemingway's boxing matches) is filled with roaming chickens and lounging cats soaking in the sun. Grab a seat outdoors under the shaded canopy or indoors in the "tree house" or dining room. Southern and Caribbean fare is served for breakfast, lunch, and dinner, but breakfast is always jam-packed. Expect jerk chicken sandwiches and shrimp melts for lunch, pork tenderloin and snapper in a citrus sauce for dinner, and at breakfast, the lobster Benedict is the way to go. Their famed key lime pie has been featured on many a TV show and is country-star Kenny Chesney's favorite. Parking is extremely limited, so walking or biking is encouraged.
Best Vegetarian: This cozy restaurant on Southard Street has been redefining vegetarian cuisine for over 10 years. With a warm Bohemian décor, their menu offers a variety of options (all clearly marked if gluten-free), which means no one has to sacrifice to have a fab meal. Craft beer and homemade sangria, usually absent at "health food" restaurants, get the conversation flowing. Omnivores will appreciate the seafood dishes like blackened mahi-mahi and P.E.I. mussels. The falafel served with bean salad, cream of tomato soup and the sweet potato fries all get rave reviews. Finish with vegan Key lime cheesecake. Everything is made from scratch, so be sure to check out the nightly specials. As always, if you have a severe gluten allergy, let the kitchen know, so they can prepare your meal properly. Grab a comfy cushioned seat in front of the window and prepare for a delightful meal.
Best Lunch: Caroline's Cafe is a favorite among tourists and locals alike for their generous portions at reasonable prices and a prime view of Duval Street. At this casual American restaurant, you'll find one of the best hamburgers in town as well as an excellent shrimp and bacon club sandwich. They also have a full menu with dishes like shrimp po' boy, jambalaya and jerk chicken. If you just want a light bite, appetizers include conch fritters, dolphin fingers, fried shrimp and more. Its location along the main drag ensures that there's usually a crowd (and sometimes a wait), but the staff is friendly and efficient. Plus the people-watching is excellent entertainment. Look out for Abby the rooster, who serves as a welcoming committee.
Best Local's Pick: This cozy restaurant mixes simple wood furnishings with splashes of yellow and orange and has additional seating on their outside patio. Partners Scot Forste and Fred Isch meld gourmet and down-home cooking, focusing on fresh island ingredients. This makes their menu the perfect middle-ground for the foodie and non-foodie alike. As if hosting a party in their own home, Isch and Forste take turns cooking family recipes and charming diners with witty stories. Start your meal with the trio appetizer: smoky-sweet grilled Key West pink shrimp with lime chutney, Caprese salad and Florida lobster mac. For an entree try their house specialty--a light flaky pan-seared yellowtail snapper entree with fresh banana salsa. Finish with the Spicy Chocolate Quesadilla. White and dark chocolate is melted between two flour tortillas and drizzled with a pepper-infused chocolate sauce.