Have all those margaritas in paradise left you with a hankering for Mexican food? Check out the small tortilla bar, Amigos, conveniently located caddy corner to the infamous Sloppy Joe's on Duval Street. You'll usually find the tiny place packed, but it's well worth the wait for their homemade square corn tortillas. You can pack more delicious fillings like chorizo, fish and shrimp into the folded square, and it's easier to hold. This equals less food spilling down the front of your shirt. Pile on their mouth-watering guacamole or chipotle corn salsa, which they make from scratch with no preservatives or chemicals. Turn up the heat with a variety of chilli/pepper sauces that range from mild to muy caliente. This open-air spot, which is open for breakfast lunch and dinner has seating right along the road--perfect for people watching.
Refuel for your night on the town at Sandy's Café, a small Cuban restaurant at the end of the M & M Laundry building on White Street. Yes, it's at a laundromat. Let this be your introduction to the funky synergy of Key West. Step up to the window and order a colada, an espresso-style brew to share, or a café con leche, a Latin latte with steamed milk. Try the Midnight (Medianoche) sandwich, which got its name from being a staple served in Havana's night clubs right around or after midnight. Similar to the traditional Cuban sandwich, roast pork, ham, mustard, Swiss cheese, and dill pickles are pressed between warm slices of soft, sweet egg dough bread similar to Challah.
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. It's called "a great place if you can find it" for a reason. Print out directions or use your GPS.
This award-winning 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 caramel-dipped wine glass dusted with 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. It's no surprise that they've been voted the top decadent dessert spot United States. Reservations are a must.
POINT5 is the kind of hidden gem you're most likely to find on a local's advice. To get there you have to climb a set of creaky stairs on the side of a repurposed Victorian home, which houses the restaurant Nine One Five below. You can jockey for one of the chairs at the small square bar or sit out on their wraparound patio watching the parade of people passing below on Duval Street. Being above the raucous masses allows you to kick back with a glass of vino and tapas until midnight. Their fusion menu roams the globe from Vietnamese Chicken Rolls to a Mezze Plate with tzatziki and stuffed grape leaves. Thin crust pizzas come with inventive toppings like duck confit or ham and eggs. DJ George spins an eclectic mix of funk and soul during Destination Boogie until 2:00 a.m. on Saturday nights.
Tucked behind La Trattoria restaurant, Virgilio's (named after the founder of the restaurant) is an elegant indoor/outdoor cocktail bar popular with the swanky over 30 crowd. Perfectly mixed martinis are the house specialty in yummy flavors like mint chocolate chip and Key lime pie. If you have trouble choosing from their extensive selection, the bartenders can help you find the right drink to fit your mood. Kick back either on the outside patio or at the second bar under the roof. Every night people hit the dance floor for live music, usually jazz, blues or Latin. If you're feeling peckish, you can order Italian fare from a limited menu by La Trattoria. Don't miss Martini Mondays when all their martinis are just $5.
Located in the heart of the action on Duval, Fogarty's is a one-stop spot for people-watching, scrumptious frozen drinks and a diverse menu. Expanding beyond the typical bar fare, they offer a diverse selection of appetizers and entrees highlighting the local seafood at reasonable prices. Start with the Key West Crab Cakes appetizer made with lump blue crab and their homemade remoulade sauce. Move on to the Pecan Encrusted Mahi-Mahi, a fresh filet brushed with honey, coated in pecans, deglazed with chardonnay and a Key West Sunset Sauce. If you've had your fill of seafood, go for the blackened rib eye or filet mignon. Enjoy the open-air patio or seek sanctuary inside the air conditioned dining room. At their Flying Monkeys Saloon, they have all the standard frozen cocktails, as well as a few originals like the Dirty Monkey--a Banana Breeze (vodka, vanilla ice cream and bananas) mixed with Chocohol.
Popular for their raw bar and must-have souvenir t-shirts, Hog's Breath has earned its share of die-hard fans over the past 20 plus years. Live music is on tap three times a day with performers who engage the crowd with witty banter and sing-alongs. Even Kenny Chesney has been known to pop in for an impromptu concert. Pick between the tropical patio or the indoor air conditioned dining room to nosh on a variety of dishes that are a step above your normal fried bar food. Try some island favorites like traditional Bahamian conch chowder or fish tacos with seasoned grilled mahi-mahi. In a nod to their name, you can also find roast pork dishes like the mini pork shank Hog Legs. This lively bar is known for loud music and raucous fun, so chase your meal with a Key Lime Shooter instead of pie.
The go-to bar for sports fans, Jack Flats has all the top games on one of their 19 big screen TVs. It's also a popular lunch spot for locals who appreciate the generous portions of home-style favorites like pot roast and meatloaf at reasonable prices. Their shrimp and bacon club and monster hamburgers also draw ardent fans. On game-day, order the pretzel bread appetizer with gooey cheese followed by the mahi sliders for the table to share. Wash it all down with beer from their extensive selection. Note that this is not the spot for a quiet meal, as the crowd can get rowdy, but good eats after midnight are hard to find. Plus your server can bring you a sound box to the table, so you can hear the game that you are watching above the din.
Pizza is the epitome of post-drinking foods, and Mr. Z's is the best spot to stop for a quick slice on the way home. Starting at $2.50 per slice, it's probably the cheapest meal you'll have during your entire vacation. Open to 4:00 a.m. this New York style pizza joint usually has a line out the door after midnight. The owners are from Philly, so you'll also find authentic cheesesteak sandwiches, served with their "Famous" American Cheese Sauce. Watching the cooks whip up the sandwiches is half the fun. Other popular hot sandwiches include the Roast Pork Italiano (a whopping $7) with spicy broccoli rabe and sharp provolone. While the interior is bare-bones, most of their business is take-out and delivery. During the day, it's a great pit stop for a grab-and-go snack in between sightseeing.