Oldest Restaurants in Key West

You can’t talk about things to do in Key West without discussing the many terrific restaurants you’ll find there. Mixed in with fast food and trendy new hot spots, you will find some of the oldest restaurants that offer the best dining experiences around. These well-loved eateries have atmosphere and style that you won’t find in the contemporary world.

Pepe’s Café and Steakhouse

Pepe’s is the oldest restaurant in the Florida Keys. Established in 1909, it can be found on Caroline Street along the old commercial waterfront. Each day starts with a hardy breakfast of traditional favorites and home-made sweet breads. At lunch, this is a great spot to grab a sandwich, soup, or chili at the outdoor seating. Dinner is when this place takes center stage with its customer favorite, the 15 ounce New York Strip “Dinner for Two” served in the rustic indoor dining area. Top it off with homemade dessert or a drink during the daily happy hour.

Blue Heaven

Here you’ll feel like you’re stepping back in time to a perfect outdoor Caribbean dive. One hundred years ago, this place started out selling spirits to the area residents. Today the rustic charm adds to the appeal as chickens run about and cats cozy up to the guests. Sit down to a table of miss matched furniture to enjoy traditional Key West dishes. Their shrimp melt is a must have. This “days gone by” spot can be found on Thomas Street.

El Siboney Restaurant

This authentic Cuban spot is found on Catherine Street in Old Town. It is a true hidden treasure that sits a bit back from the bigger crowds of tourists. Once you find El Siboney, you’re rewarded with great dishes like the sliced roast pork with onions and rice. Along with affordable prices, the beer and house made Sangria are favorites among tourists and locals alike.

Seven Fish

A corner fish bistro, the Seven Fish is the place that serves up all your seaside favorite dishes. Try the sea scallops over mashed potatoes with spinach and pea puree for a true Key West treat. The restaurant includes a full bar that has become one of the best things to do in Key West. Its tight quarters inside, so be sure to make a reservation well ahead of time. This comfortable and casual eatery is just off of Duval Street.

Hogfish Bar and Grill

This restaurant is a bit out of the way in Stock Island’s Safe Harbor, but it is well worth the trip. Here you’ll experience how the Florida Keys used to be. It’s a favorite for seafood among the locals. Enjoy the seaside setting along with great dishes like the Hogfish sandwich on Cuban bread. If you bring your own fresh catch, the kitchen will gladly prepare it for you and serve it with fries, rice, and vegetables. You’ll find the Hogfish Bar and Grill on Front Street.

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