Chowing down in Old Town: 10Best restaurants in the Key West Historic District

Restaurants in Old Town, Key West aren't known for being cheap, but there are several that are well worth a splurge and others that offer great value for your dollar. Fresh seafood is on every menu, and there's a wide variety of international cuisines like Cuban, Italian, Spanish, Bahamian and more. 

For a romantic Italian establishment, La Trattoria offers a fine-dining atmosphere and excellent pasta dishes while Duetto's Pizza and Gelato offers take out and delivery. Michael's is a long-time favorite with several options, ranging from fresh pasta to strip steaks.

For fresh seafood dishes, Azur continues to deliver quality and service for a reasonable price and after dinner, you can stop by Better Than Sex for scandalously decadent desserts and fine wines.

Hit up El Siboney for a taste of the Cuban flavor that permeates the island. Make sure to have the super-leaded cafe con leche to keep you going.

Many tourists head to Blue Heaven for a laid-back breakfast or brunch. The wait will be long, but the restaurant lives up to the hype. No matter what type of restaurant you are looking for, our "Best of Old Town" selections will help you find a table.


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.

Recommended for Old Town's Best Restaurants 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: It's so scandalous that reservations are advised.

Read more about Better Than Sex →

Santiago's Bodega
Photo courtesy of Santiago's Bodega

A colorful walk through Bahama Village brings you to this bright cozy restaurant tucked away behind lovely landscaping. Their tasty Spanish tapas are the perfect size for a light lunch, and the indoor seating provides a welcome respite from the mid-day sun. In the evenings, this spot is packed, and reservations are a must. At lunch, things move a slower pace, and you should be able to saunter in on your own schedule. Order a pitcher of their sparkling sangria to beat the heat. At some restaurants, "tapas" equals painfully small plates, but at Santiago's, the portions are generous. Standout dishes include the Saganaki-halloumi cheese sprinkled with oregano flambeed with Brandy. Other faves have an equally artful presentation like the Fresh Yellowfin Ceviche, which is marinated in spicy citrus juice and served with fresh avocado, mango and cilantro. Finish with their homemade bread pudding with caramel bourbon sauce.

Recommended for Old Town's Best Restaurants because: Santiago's scrumptious tapas are perfect for sharing. Order several for the group and dig in. Pair with a few pitchers of sparkling sangria.

Claudia's expert tip: Santiago's happy hour (3-6 pm) is the perfect time to sample several varieties of tapas at $5 a pop. Pair with a discounted pitcher of sangria.

Read more about Santiago's Bodega →

A trip to Key West wouldn't be complete without sampling some authentic Cuban cuisine, and El Siboney's is the place to do it. Hidden in a residential area, from the outside this eatery is just an average, brick building. Don't be fooled by its simplicity; this restaurant is a local gem. Shrimp enchilado, roast pork, and two-person paella are just a few of the mouthwatering menu items, plus there are daily specials. Some of the wait staff speak very little English, but that's what menus are for. Prices are very reasonable and the restaurant is family-friendly, but as with many Key West restaurants, expect a wait during busy.

Recommended for Old Town's Best Restaurants because: This no-frills place serves Cuban food that's as close as you can get to being in Cuba, literally.

Claudia's expert tip: Watch the daily specials for some real treats like the white bean soup on Mondays and Oxtail on Saturdays.

Read more about El Siboney →


This Mediterranean-inspired restaurant serves breakfast, lunch and dinner, which means couples can steal away for a romantic meal no matter what time of day. It features a shaded terrace and trickling waterfall for outdoor dining, as well as comfortable indoor seating. A popular Sunday brunch destination, they offer items like Key Lime Stuffed French Toast, Yellowtail Snapper Benedict, hummus salad and roasted pork sandwiches with fontina cheese. The two chefs' European influences really shine on the dinner menu with tasting plates like the Walnut Filled Eggplant topped with a pomegranate reduction and entrees such as the homemade Ratatouille Gnocchi with manchego cheese. The Grinnell Street location is refreshingly off-the-beaten-path. Reservations are recommended during peak hours.

Recommended for Old Town's Best Restaurants because: This Mediterranean-inspired restaurant draws locals and visitors alike with creative brunch dishes like Gnocchi Fritattas and Yellowtail Snapper Benedict.

Claudia's expert tip: The house-made gnocchi is a must-try, cooked to perfection with four different options to choose from like wild mushroom or ratatouille.

Read more about AZUR →

At Duetto, the friendly owners, Leonardo and Giancarlo, offer samples of their homemade creamy gelato. With so many flavors to chose from, you'll be back for more!! Flavors include coconut, pistachio, hazelnut, and chocolate rum, all that pair perfectly with an espresso! The cafe also serves award-winning pizzas stuffed with prosciutto, salami, olives, fresh tomatoes, anchovies and mozzarella cheese. All of their pizzas are Italian style, thin crust, 16" pies with six slices. The roast beef panini melts in your mouth, and if you still have room take one of their baked goods to go. It's location on Greene Street, just around the corner from Sloppy Joe's, makes it perfect for carry-out.

Recommended for Old Town's Best Restaurants because: Duetto's serves real Italian pizza and gelato in Old Town that will have you coming back the next day!

Claudia's expert tip: Ask them to mix a flavor or two for you!

Read more about Duetto Pizza and Gelato →

Duval Street
La Trattoria

This spot has everything a high-end Italian restaurant should have: friendly staff, warm ambiance, excellent location and homemade pasta. Snack on bruschetta or prosciutto with melon while you read the menu. The penne Venezia is tossed with mushrooms, sun-dried tomatoes and crabmeat. The cannelloni is stuffed with veal and spinach. Or for something lighter, try the eggplant stuffed with ricotta and roasted peppers. The wait staff will help find a wine to pair with your entree, and homemade tiramisu is a dessert that properly tops off any meal. After dinner, stop by Virgilio's martini bar behind the restaurant for live jazz and artfully-crafted cocktails.

Recommended for Old Town's Best Restaurants because: For classic fine dining and Italian cuisine, you can't go wrong with La Trattoria.

Claudia's expert tip: On Mondays, the martinis are just $7.

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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.

Recommended for Old Town's Best Restaurants because: Slow down and enjoy your meal in their private courtyard where chickens roam, cats soak in the sun and live music lingers in the air.

Claudia's expert tip: Check out their Rooster Gallery next door, a cute little gift shop you'll love.

Read more about Blue Heaven →

Escape to this private island for elegant toes-in-the-sand dining and panoramic Gulf views. After a quick ride on the ferry from Old Town Key West to Sunset Key, settle in at Latitudes for dinner and a show, the stunning sunset. With sailboats gliding past, you'll feel like a VIP, as well-trained servers bring bring lobster stuffed crab cake, savory lobster bisque and pickled Key West Pink Shrimp to your table, and those are just the appetizers. Latitudes rounds out the seasonal menu with tantalizing selections like pan-roasted rosemary cobia, Wagyu beef skirt steak and seafood pasta. Make sure you save room for dessert. You'll want to relax on this slice of paradise as long as possible. Try the beignets, light puffs of doughy goodness so delicious you may not want to share. Have your camera ready as the sun drops from the heavens, you'll be hard-pressed to find a better perch. Reservations are required, so arrive a few minutes early for the ferry

Recommended for Old Town's Best Restaurants because: Indulge in a little luxury, as you escape to this private island for elegant toes-in-the-sand dining and panoramic Gulf views.

Claudia's expert tip: While the tables on the sand have the best ambiance, be prepared for full exposure to the warm rays at sunset.

Read more about Latitudes Sunset Key →

This cozy restaurant on Southard Street has been redefining vegetarian cuisine for over 10 years. With a warm Bohemian d├ęcor, 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.

Recommended for Old Town's Best Restaurants because: Redefining vegetarian cuisine for over 10 years, The Cafe offers creative dishes for all diets, ensuring all diners will have a fab meal.

Claudia's expert tip: Check out their nightly specials, which range from chickpea and squash tacos to vegan double chocolate chip cake.

Read more about The Cafe →

After 20 years of having a small, low-key bistro, Seven Fish upgraded to a spacious and airy restaurant on Truman Avenue. While the building may be new, the menu has stayed the same, featuring its simple, yet elegant approach to cuisine. Seven Fish mixes both fresh seafood and comfort foods like meatloaf on their menu. Start with the fish tacos or the wild mushroom quesadilla followed by the house specialty, Thai Curry Snapper. The type of fish offered each night varies according to the season and catch of the day. Tired of seafood? Try the Banana Chicken with caramelized walnuts. Since it's popular with tourists and locals alike, making a reservation well in advance is highly recommended. If you're feeling more spontaneous, sometimes you can score a seat at the bar last minute. Note: they are closed on Tuesdays and for several weeks in the fall.

Recommended for Old Town's Best Restaurants because: This neighborhood bistro is tops for their simple, yet elegant approach to fresh fish. Try it paired with the Thai curry cream sauce.

Claudia's expert tip: Don't miss their strawberry whipped cream pie with a chocolate graham cracker crust; it's a slice of heaven.

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Meet Claudia Miller

Claudia Miller has been writing about South Florida for over 17 years--seven from Key Largo. A budding photographer, she can usually be found stalking a sunset. Despite being a tad...  More About Claudia