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 just about every menu, and but there is a wide variety of international cuisines to choose from as well. As the name states, Colombian Grace serves homemade family recipes from Colombia, while El Siboney offers authentic Cuban dishes.

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.

10 Better Than Sex
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. ((305) 296-8102)

9 Santiago's Bodega
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. ((305) 296-7691)

8 El Siboney
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. (305-296-4184)

7 2 Cents
Who knew something as simple as "free bacon" would lure so many people to a restaurant? The new gastropub tucked away on Appelrouth Lane dangled that carrot is now witnessing the results. Foodies, bacon lovers, and their dogs have found a new safe haven at this pet-friendly restaurant, which opened in January 2012. Funky decor consisting of re-used "junk" material like discarded safety deposit boxes (which make the bench) and graffiti-painted walls add to the atmosphere, and the outdoor garden makes for a brunch oasis.Sunday brunch items are far from the ordinary French toast and omelets: expect poblano rellenos with olive oil poached tuna, Scotch eggs with IPA mustard sauce, and grilled turkey with fried green tomatoes. ((305) 414-8626)

6 Azur
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. (1-305-292-2987)

5 Colombian Grace
A new addition to the Bahama Village, the focus at Colombian Grace is fresh ingredients, and traditional family recipes. As the only Colombian restaurant in the Florida Keys, it is setting the standard with fresh squeezed orange, grapefruit, lulo, and pineapple juices, coffee from the family farm in Colombia, and local seafood "gracing" many of the dishes. Menu items range from "Mom's Casserole" with fresh grouper, fish broth, and mozzarella cheese, to the "Artisan Tamales" that are wrapped in banana leaves and broiled to order (and are well worth the 30 minute wait). Stop by on the weekends for a morning breakfast of fresh eggs, bacon, and chorizo, washed down with Grandma's hot chocolate. Specialty breakfast items include eggs over fried green plantains with melted cheese, or accompanied by roasted corn, red beans and white corn cakes. (305 240 1281)

4 Michaels Restaurant
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. (305-295-1300)

3 Duetto Pizza and Gelato
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! ((305) 848-4981)

2 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. (305-296-1075, 305-293-8169)

1 Blue Heaven
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. (305-296-8666)


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 places are Iceland for its remoteness; Panama for its parties; and Peru for its history. Her work can be found on MSNBC.com, Frommers, and Sherman’s Travel, where she served as the Cruise Editor and Senior Producer. She is currently working on a comic novel about her shoestring travels as she hitchhikes on airplanes across the country in an effort to visit all 50 states. See Jethiking.com.

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Maps and Directions

2
Santiago's Bodega 10Best List Arrow
Cuisine: European, Spanish
COST: $
3
El Siboney 10Best List Arrow
Cuisine: Cuban, European, Latin, Spanish
Dining Options: Family Friendly, Non-Smoking, Take Out
Neighborhood: Old Town
COST: $
4
2 Cents 10Best List Arrow
Cuisine: American
Neighborhood: Old Town
COST: $$
5
Azur 10Best List Arrow
Cuisine: American
Neighborhood: Old Town
COST: $$
7
Michaels Restaurant 10Best List Arrow
Cuisine: American, Steakhouse
Dining Options: Bar / Lounge, Bar Dining, Parties / Private Rooms, Smoking (bar only)
COST: $$$
8
Duetto Pizza and Gelato 10Best List Arrow
Cuisine: European, Italian
Neighborhood: Old Town
9
La Trattoria 10Best List Arrow
Cuisine: European, Italian
Dining Options: Family Friendly
COST: $$
10
Blue Heaven 10Best List Arrow
Cuisine: American, Vegetarian
Dining Options: Family Friendly
Neighborhood: Bahama Village
COST: $$