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.
Recommended for Late Night because: Get your Mexican fix until midnight with their signature square tortillas packed with refreshing slaws and mouth-scorching sauces.
Claudia's expert tip: Vegetarians rejoice! You can order any of their items sans meat. Plus everything on their menu is 95% gluten free.
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.
Recommended for Late Night because: Open 24 hours, this Cuban walk-up window provides the high-octane coffee and aptly-named Midnight sandwich guaranteed to keep you partying until dawn.
Claudia's expert tip: Sandy's only accepts cash.
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.
Recommended for Late Night because: Kick back local's style til midnight at this open-air eatery known for its Old Key West vibe and killer hogfish sandwich.
Claudia's expert tip: Local musicians turn it up a notch with live performances on the weekends.
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.
Recommended for Late Night because: It's never too late for dessert at Better Than Sex, where you can indulge in decadent treats with scandalous names until midnight.
Claudia's expert tip: Portions are generous, so you may want to share.
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.
Recommended for Late Night because: Those in-the-know climb above the restaurant to POINT5 for European-inspired tapas and pizzas until midnight, while people-watching from the outdoor patio.
Claudia's expert tip: For chilling with friends under the stars, they also have a back deck with comfy chairs and a lounge vibe.
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 full menu until 10:30pm, and from a limited menu until close. Don't miss Martini Mondays when all their martinis are just $5.
Recommended for Late Night because: With it's sexy speakeasy vibe, Virgilio's pairs Italian paninis and appetizers with perfectly mixed martinis until 4:00 a.m. on weekends.
Claudia's expert tip: Dress to impress and wear your dancing shoes. They have live music seven nights a week.
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.
Recommended for Late Night because: Fogarty's showcases the fresh local seafood with generous portions at reasonable prices well into the night. Their delicious frozen drinks double as desserts.
Claudia's expert tip: If you fall in love with their frozen drinks, spring for their squeeze bottles for $10, and refills will only cost you $7.
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.
Recommended for Late Night because: With its famous raw bar and well-rounded menu, Hog's Breath offers a step above your standard bar fare until the wee hours.
Claudia's expert tip: Check the entertainment schedule on their website to see which bands are playing; they have three different ones each day.
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.
Recommended for Late Night because: Sports fans love the 19 big screen TVs and a menu that pairs home-style faves and monster hamburgers with shrimp clubs and mahi sliders.
Claudia's expert tip: At first glance, Jack Flats may look small and crowded. Just keep walking towards the back where a long bar runs the length of the building.
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.
Recommended for Late Night because: Mr. Z's is the best spot to stop for a quick slice until 4:00 a.m., and the authentic Philly cheesesteak sandwiches are a bonus.
Claudia's expert tip: Their stromboli is homemade and baked to order, which takes about 25 minutes. Either be prepared to wait or call ahead.