If you’re headed to the Southernmost Point of the United States, you better get your list of restaurants ready. Key West might be a small town, but its food options are mighty. In Cayo Hueso, you’ll find only the freshest seafood, caught on the daily, authentic Cuban cuisine, flaky French pastries, raw oysters. and more. The good thing is, no matter the meal, you’ll never be underdressed; showing up for lunch in a bikini might sound questionable, but in the Keys, comfort takes precedent.
Hogfish Bar & Grill
Located on Stock Island at the Safe Harbor Marina, Hogfish Bar & Grill offers casual waterfront dining with all the views (whether you sit in or outdoors), live music on weekends and, of course, fresh, local seafood. Known as a locals spot, Hogfish serves up a Hogfish Sandwich on freshly-made Cuban bread, with Swiss cheese, mushrooms, and onions; tacos are on the menu here, too. If you spent the day out fishing, the restaurant will happily cook your catch for just $14.95 per pound, per person. They will serve it to you blackened or grilled, with rice or fries, and veggies.
This family-friendly Cuban restaurant serves up tradition on a plate and the best darn housemade sangria you’ve ever had. With two locations on the island (one on Catherine Street and one a little further north on Stock Island), you can always grab a meal here without having to go very far. Check out El Siboney’s daily specials, like chicken fricassee or oxtail; each comes with a choice of white or yellow rice, black beans or a soup of the day, and sweet plantains or cassava (a root vegetable commonly known as yuca).
This charming all-American spot in a 100-year-old building is perfect for breakfast, lunch or dinner, though it started as mainly a lunch place in 1992. Grab a table on the open-air patio and be prepared to share your space with the restaurant's chickens and kitties. Don’t worry; they’re friendly and add a little entertainment to your dining experience. The wait to be seated can be long here, but menu items like eggs benedict, pecan pancakes, and shrimp and grits make it all worth it. For dinner, try the Jamaican jerk chicken and don’t leave without dessert. Both the key lime pie and the banana heaven (Betty’s banana bread, banana flambe with rum and homemade vanilla ice cream) are solid choices.
Eaton Street Seafood Market & Restaurant
What can we say about Eaton Street Seafood that hasn’t already been said? This gas station-style seafood market is a dream come true. Step inside and place your order based on what’s available in the glass cases; everything is fished fresh daily. Once you’ve ordered, head outside and choose a spot at the outdoor picnic tables to devour your lobster roll, smoked fish dip and Cuban crackers, sizzling grouper sandwich or stone crabs. In the heart of historic Old Key West, Eaton Street is a precious gem that never fails a hungry person with good taste. Take some marinades and spices to go, or some ceviche for the road. You can’t go wrong here, no matter what you order.
Caribbean-American food and an ocean view? Sold. Louie’s Backyard has been open for nearly 50 years, and what started as just a 12-seater spot has expanded to a cafe-style restaurant serving local food by Chef Doug Shook, who’s been with the restaurant for more than 30 years now. The emphasis here is on “hooked” local fish, meaning it’s cooked and served right off the hook or shortly after being caught. You can try everything from snapper and swordfish to grouper and hogfish. Lobster is a must here, as are all the land dishes like heirloom pork, free-range chicken, and the double lamb chop. Fruits and vegetables are locally grown, as well, and include all the glorious tropical produce found on the island like mango, papaya, guava, starfruit, and lychee.
Nine One Five Restaurant & Bar
Smack in the middle of Duval Street and all the action, Nine One Five has Chef Brendan Orr at the helm, who combines New Island cuisine with fresh and authentic ingredients, Caribbean spices, Asian influences, and French technique. The restaurant specializes in dishes like peking duck confit, chipotle pork tacos, Florida Keys lobster ravioli, whole yellowtail snapper, and filet au poivre—an 8-ounce prime filet served with green peppercorn sauce, watercress salad, and fries. The restaurant is a sister spot to First Flight Island Restaurant & Brewery and Bagatelle, too, so before or after your decadent dining experience you might want to check out the group’s other restaurants for a glass of wine or a local brew.
Half Shell Raw Bar
There is so much to say about Half Shell, it’s hard to sum up in just a few sentences. This casual indoor/outdoor eatery combines just the perfect amount of crass and class. Decorated from top to bottom with dollar bills and license plates, it’s not uncommon to share your eating space here with pelicans, cats, and those who had a few too many drinks. Go for the raw oysters; stay for the ambiance, cocktails, music, and good time.
Frita's Cuban Burgers
Frita’s is basically a tiki hut with walls and we love its style and simplicity so, so much. Decorated with variations of Frida Kahlo and other mustached and unibrowed artworks, Frita’s serves up beef and pork burgers, arepas and fritas—a classic and super savory, Cuban sandwich. If you’ve never heard of a frita, you’re missing out. The beef and pork patty burger seasoned with Spanish spices is otherworldly and gets even better with garlic, onion, (secret) frita sauce, and house-made julienned potatoes. It’s served on a Cuban roll and the traditional version includes the option of American or Manchego cheese and an egg on top.