Everyone who visits Key West knows about Duval Street. In addition to all of the ever changing shops that line Duval Street, it is home to bars like Sloppy Joe’s, restaurants like Banana Cafe, museums like the Oldest House, and art galleries like Wyland. But, the iconic yet lesser known Caroline Street also houses many gems as well.
Caroline Street, situated on the northwestern side of Key West, runs perpendicular to Duval Street, and is one of the oldest roads on the island. It was part of the original layout when mapped our by William Whitehead, who is also immortalized by an island street bearing his name. This street is named for one of his siblings.
At one end of Caroline Street, Dante’s Bar & Restaurant can be found. At the other, Truman Annex, a gorgeous neighborhood on what was once Navy property. In between, one can find many other treasures. Restaurants, bars, places to stay, museums, island stores and even parking areas line this street! Many old “conch” houses, some of which have belonged to famous persons, also line this street’s residential section.
Dante’s – 951 Caroline Street is home to this restaurant known not only for its food, but also for its pool open to the public.
Prime – 951 Caroline Street is where you can find Key West’s premier steakhouse.
Off the Hook – Located at 920 Caroline Street is a favorite of ours. This American bistro style eatery serves locally sourced seafood, pizza and more. Plus they have amazing music and happy hour specials.
Onlywood – At 725 Caroline Street you will find this wood fire pizzeria and restaurant serving up some good Italian food in a trendy atmosphere.
BO’s – Located at 801 Caroline Street, this driftwood shack has been serving fried fish, conch fritters, and sandwiches for decades.
Harpoon Harry’s – Found at 832 Caroline Street, this quirky cash only diner where you can get a delicious breakfast, lunch or dinner at a reasonable price.
Pepe’s – Located at 806 Caroline Street, this laid back restaurant has been serving up delicious fare in Key West since 1909.
The Bull & Whistle Bar – Located at 437 Caroline Street, this is really three bars. The Bull is open air and features live music nightly. On the second floor, the Whistle houses pool tables, games and a balcony overlooking Duval Street. On the roof is another bar Known as the Garden of Eden, a clothing optional bar.
Fast Buck Freddie’s – After thirty-seven years on Duval Street, the store closed due to sky high rents. Fast Bucks at Home, located at 726 Caroline, has a great selection of furniture, gifts, accessories and select imports. Always something fun to find here.
Key West Marine Hardware – Located at 818 Caroline Street. Also known as Los Cubanitos, a staple store for marine supplies and fishing tackle in Key West for many years.
Museums / Historic Homes
Flagler Station – Located at 901 Caroline Street. The Sails to Rails Museum teaches visitors about a time when tall ships ruled the waters and railroads opened the frontiers. And, a time when Key West was the richest city per capita in the country.
Capt. George Carey House – Located at 410 Caroline Street, this house was built in 1834 by Captain George Carey. In 1934, the house was purchased and restored by Jesse Porter who lived there until her death in 1979. She hosted many famous visitors including Ernest Hemingway. And, the small cottage located to the right of the house is named for the poet Robert Frost. He spent sixteen winters there as a guest, writing some of his most famous works.
Richard Kemp House (Kimpton’s Ridley House) – Located at 601 Caroline Street. Formerly the Cypress House B&B, industrialist Richard Kemp built Ridley House in the late 1800s. Kimpton refined the historic building with contemporary touches. And, with a pool and tropical foliage, the grounds are a tropical paradise for vacationers.
Curry Mansion Inn – Located at 511 Caroline Street. William Curry, considered to be the first self-made millionaire in the State of Florida, built his home in 1869. In 1901, his son Milton demolished almost all but the cook house to construct the elaborate Georgian Revival mansion that stands today. The house was turned into a bed and breakfast in 1988 and has been operating continuously since. It is also open daily for tours.
More About Key West
Island Genn – Key West Concierge