Places to Visit on a Road Trip from Miami to Key West

Key West Road Trip: Six Sites Worth a Pit Stop

• Stiltsville

  These “floating houses,” situated in Miami’s Biscayne Bay on the northernmost reaches of the Keys, first popped up in the 1930’s. They’ve served as everything from fishing campouts to illegal bars to uninhabited relics, but have retained a mysterious allure from the beginning. Nowadays, you need a permit to visit (the place is a protected area), but they can still be seen at a distance if you’re sailing by.

• Ernest Hemingway House

  Key West’s Ernest Hemingway House is arguably South Florida’s most famous dwelling. It was built in1851 by the architect Asa Tift, and Hemingway moved there in 1931after purchasing the estate for a grand total of $8,000. Some oddball facts about the place: several descendants of Hemingway’s cats still live here, many with extra-toes (polydactyls). Also, a James Bond movie, License to Kill, was filmed here in the 1980’s.

• Lorelei Restaurant

  OK, this isn’t a home, but it is a classic Keys institution. Stop in for some fish dip, a strong drink, and some conch fritters. (Also, fans of Netflix’s Bloodline will appreciate that much of the series is filmed in the restaurant’s town, Islamorada. Lorelei even makes a cameo.)

• Ballast Key

  This private island—currently for sale for around $15,000,000—is the southernmost point in the United States. It boasts 26 acres, including two homes, and is marketed with the catchphrase “your closest neighbor is eight miles away.” (Also, back in the day, Tennessee Williams and Truman Capote were frequent visitors.)

• The Moorings Hotel

  Also located in Islamorada, The Moorings Hotel is, perhaps, the most luxurious property in the Florida Keys. Set on 18 acres, the lodge has a main building along with 14 additional cottages. And, to the previous point about Bloodline, is the focal point of the show. If you like sport fishing of any kind, Islamorada is the place to be—and The Moorings the place to stay.

• Pigeon Key

  Pigeon Key is a tiny island located in Marathon beneath the old Seven Mile Bridge that now serves as a marine research facility. You can take a tour of the place, but hanging out on the ramp and watching the eagle rays glide by below is just as enjoyable.