Best Restaurants in the Old Town District of Key West



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 a 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 newcomer 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.

Two other newcomers have quickly shown that they are rising stars: Santiago's Bodega, which offers mouthwatering tapas, and 2 Cents, a gastropub that attracts visitors with "free bacon" and an eclectic menu.

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



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This flirtatious dessert shop is proof that New Year's resolutions do come true! When husband-and-wife team Dani and Len decided that they would open a restaurant, little did they know just five months later it was on its way to becoming one of the most talked about places in the Keys for its decadent pastries, chocolate-covered wine glasses, and sensual atmosphere. Dimly-lit tables set the mood, with flashlights on the tables for guests to read the "suggestive" menu items like "Between My Red Velvet Sheets" cheesecake, and "The Missionary" apple crisp. It makes a great romantic, after dinner stop that will set the mood.


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From the outside, Santiago's Bodega looks like an old home that displays a weathered wooden sign above the entrance with a name implying it's a corner store. The interior is romantic, yet casual with mixed-matched furniture, chestnut-shaded wood floors, and dimmed lighting fixtures. The menu, which consists of tapas dishes, is equally as surprising. Start lunch or dinner off with their red sangria followed by soups, salads, and a selection of hot and cold tapas. Expect yellowfin tuna ceviche, beef Carpaccio with capers and truffle oil, lamp patties with thyme and sherry, and spanakopita (Greek spinach pie) - to name a few.


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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.


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This Mediterranean-inspired restaurant features a shaded terrace and trickling waterfall for outdoor dining, as well as comfortable indoor seating. AZUR serves breakfast, lunch, dinner, and Sunday brunch which includes items like Greek yogurt with tropical fruit and granola, Yellowtail snapper Benedict, hummus salad, and roasted pork sandwiches with fontina cheese. They also offer tantalizing daily specials like Key Lime stuffed French Toast: think thick slices of Texas toast that is topped with wild berry compote. Although a bit pricier than most brunch spots, Azur offers a unique menu and the Grinnell Street location it is refreshingly off-the-beaten path. Reservations are recommended during peak hours.


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Chef Michael Wilson and his wife Melanie add an island twist to Italian and American cuisine. Michaels' steaks are 100% prime beef, flown in from Allen Brothers of Chicago and the seafood selections change nightly. For a special treat, Michaels Restaurant offers fondue at the garden bar when include breads, fruits, vegetables, roasted shallots, and various meats for dipping. Dinner may include items like veal saltimbocca with cream sauce, stuffed chicken with prosciutto and sun-dried tomatoes, or seafood alfredo with pink shrimp, mahi mahi, and grouper. Large, shaded trees grow next to the tables in the outdoor courtyard, providing a romantic setting for a night out.


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This new venue won't be kept a secret for long! The friendly owners, Leonardo and Giancarlo, offer samples of their creamy gelato that is homemade using milk imported from Italy. Once you try their fantastic gelato, 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 pizzas stuffed with prosciutto, salami, olives, fresh tomatoes, anchovies and mozzarella cheese. The roast beef panini melts in your mouth, and if you still have room take one of their baked goods to go. With a location on Green Street, the crowds will find it soon!


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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 proscuitto 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.


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In Key West, this restaurant needs little introduction. Enter a private courtyard to find roaming chickens, lounging cats soaking in the sun, and live music lingering in the air. 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 citrus sauce for dinner, and at breakfast, the lobster Benedict is the way to go. Parking is extremely limited, so to be courteous to the neighbors walking or bike riding is encouraged.


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Indulge in a little luxury, as you and your honey escape to this private island for elegant toes-in-the-sand dining and panoramic Gulf views. After a quick ride on the ferry across the Key West Harbor 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 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, arrive a few minutes early for the ferry.


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Meet Amber Nolan

Originally from upstate New York, this restless traveler has a knack for befriending interesting characters. You can usually find her just about anywhere that has a hammock. Amber's favorite...  More About Amber

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