Caroline’s Cafe is located on part of the historic Dr. Joseph Y. Porter House. The house is believed to date to 1838 and to have been built by Judge James Webb, who was the first Federal Judge of the Southern District of the Florida Territory.
It is, however, better known as the birthplace and home of Dr. Joseph Yates Porter, II, who was Key West’s first native born physician and became one of the outstanding men in Florida’s medical history. The building was added to the U.S. National Register of Historic Places in 1973.
Opened in 1999, Caroline’s Cafe was the first of now five restaurants opened by Tropical Soup. Back then, it wasn’t uncommon to see our baby daughter, Sabrina, on someone’s hip at the hostess stand and around the restaurant. Nowadays, it’s more common to see Abby the Rooster.
The name “Caroline’s Cafe” is somewhat derived from the Jimmy Buffett Song “Woman Going Crazy on Caroline Street.” In fact, that song also gave the name to one of our signature beers from our newest restaurant, the Waterfront Brewery.
As for Caroline’s Other Side, our craft cocktail bar has been serving classic concoctions since 2014. We’re right next door to The Porch inside the historic building, easily accessed from the corner of Duval Street and Caroline Street. It’s connected to Caroline’s Cafe, too, but that winding path may feel like a journey to the other side…