601 Whitehead St, Key West, FL 33040, USA
Chances are that when you return home after your trip to Key West, someone will ask you if you went to the Green Parrot. It’s that kind of iconic bar, the kind your parents’ friends ended up at over spring break in college long ago. The bar started as a local grocery store about a hundred years ago; the building became the Brown Derby, a bar that was popular first with the submarine sailors from the naval base down the street. When the naval base closed in the ‘70s, the bar transitioned into a hangout for fishermen and local sailors and the hippies that began to drift into town. The Green Parrot still has the air of a honky-tonk, lit exclusively by spotlight and neon, with a roster of almost-nightly live music, mostly of the bluesy, rollicking sort.
8311, 111 Front St, Key West, FL 33040, USA
This wood house was originally intended as officers’ housing on the island’s naval base, but became famous as the Little White House when Harry S. Truman used it as a base of operations for several extended stays during his presidency. The house, now a museum, is dedicated to the history that took place here: Not just Truman, but Thomas Edison and presidents Taft, Eisenhower, Kennedy, Carter, and Clinton all spent time here, and several key summits took place here as well. As you walk through the house you’ll view all of the original furniture and historical elements—including Truman’s famous “The Buck Stops Here” desk sign—which have been maintained for generations. The beautiful tropical garden is surrounded by the original 1890 wrought-iron fence.
400 Front St, Key West, FL 33040, USA
The Hog’s Breath Saloon on the corner of Duval and Front Street in the heart of Old Key West has been in business since 1988. The Saloon was a hit from the day it opened. It’s a place to enjoy lunch or relax after a day of swimming, fishing, or sightseeing. The menu offers typical Key West fare: conch fritters, conch chowder, wings, salads, fresh fish, and raw bar. There is an Annual Hog’s Breath 5k Hog Trot. After the race, there’s an award ceremony at the Saloon.
601 Howard England Way
Yes, there is a fort here—a National Historic Landmark built in the mid-1800s to protect the country’s southernmost coastline—but locals know it for its excellent beach. A nice sandy expanse is a rarity in the Florida Keys—they’re surrounded by coral reefs, which make for primo fishing and diving but block the waves that are needed to produce a proper beach. But here, sand is trucked in to create a close facsimile—plus the water is wonderfully clear and calm, and there’s great snorkeling thanks to an offshore reef.
Set 110 kilometers (70 miles) south of Key West is a group of seven uninhabited islands known as the Dry Tortugas, which makes for one of the area’s top day trips. It is one of 11 national parks in Florida. Once there you can explore the historic Fort Jefferson, an enormous military facility that was under construction for 30 years (1846–1875) but never completed. The isles are surrounded by coral reefs with great snorkeling in the crystal clear blue waters, and you can also see birdlife galore. Most visitors arrive by ferry, which takes about three hours each way and includes a four-hour stay on the islands, but you can also charter a seaplane for a hefty price.
729 Thomas St, Key West, FL 33040, USA
Blue Heaven is a favorite in Key West—Jimmy Buffett even mentioned it in one of his famous beach tunes. The whimsical courtyard is filled with brightly colored tables and chairs, twinkly lights, foliage, and stray animals. The bar and restaurant is owned and operated by a husband and wife whose creative backgrounds in art and literature inspired the space. There’s a mini art gallery, a sandwich shop, and roaming roosters on the grounds. Once a boxing ring (with Ernest Hemingway as referee), the spot now pays tribute to the Caribbean, with bright accents and Cajun seasonings on the menu. Menu highlights include the scallops, which are locally celebrated, served with white wine and lemon butter with tomatoes, onions, mushrooms, and lots of garlic. Locals say the Key lime pie is one of the best in town.