Walking down Whitehead Street, one comes to the attractive Monroe County courthouse, the famous Green Parrot Bar and then the end of the road, literally. The street actually continues to the northwest, but a sign is there to tell you that Highway 1 ends right in front of the courthouse. It’s no big deal for locals, but of course tourists often want their picture taken at the “END” sign.
To the southwest of Duval Street is Key West’s Black community, known as the Bahamian Village, presumably because many of the city’s Black residents came from the Bahamas. The area is rich with architectural history, and worth a visit, despite being under attack from military base expansion at one end, and creeping gentrification at the other. Among the things worth seeing are the historic Key West Lighthouse, several old church buildings, the historic former Douglass High School, now used as a community center, and the Bahamian Market on Petronia Street, which sadly was closed in the evening when I walked past it. There are also several modern restaurants, a few boutiques, and a bed and breakfast called the Caribbean House. Although it’s a bit away from the usual tourist areas, the Bahamian Village is not to be missed.
The “Southernmost” Point of the continental United States isn’t, as a quick look at a Key West map will tell you. There is a point further south on the island, but it is behind the gates of the US Navy’s Truman Annex, and thus inaccessible to the public. So it’s more correct to say that it is the southernmost point of the continental United States that isn’t on a military base. There! How’s that for accuracy?
If the northwestern end of Key West’s Duval Street is mostly restaurants and bars, the southeastern half of the street is largely given over to exquisite and interesting shops, including an upscale streetwear boutique called Evolution, a reggae shop called Island Mystique, a gelato bar, a shop of Cuban goods and the occasional restaurant or boutique hotel.
Anyone familiar with Ernest Hemingway is likely familiar with his love of Key West, and probably also with his love for Sloppy Joe’s Bar. But Sloppy Joe’s in his day was not where it is now, but rather at what is today the location of Captain Tony’s Saloon on Greene Street south of Duval. Of course you can pretty well get liquor in either one, but for those inclined to history, Captain Tony’s is the actual location where Hemingway got hammered.
At the foot of Duval Street next to the Ocean Key and Pier House resorts is Sunset Pier, a pier and bar that is popular in the afternoons and evenings because of its tropical ambiance and beautiful views of the gulf and of nearby Sunset Key. There is a small stage, and in the evenings there is occasionally live music on the pier.
Key West’s Front Street is the street nearest the water in the city’s entertainment district. It runs from the A & B Marina along the waterfront to the Pier House and Ocean Key resorts, and it is lined with several shops and restaurants.
The Overseas Highway ends at Key West,a charming resort town with a colorful past. The center of its vibrant nightlife is Duval Street, lined with an amazing variety of restaurants, bars, lounges and the occasional hotel, most located in historic old houses and buildings whose architecture resembles that of New Orleans. The most famous night spot is Sloppy Joe’s Bar, which was Ernest Hemingway’s favorite drinking establishment, although it wasn’t located on Duval in his day, but rather to the south on Greene Street, where there is another bar nowadays. The area of the city known as the “Old Town” is easily walkable, but watch out for the feral roosters, who roam the streets and yards at will. They are said to be descended from those brought to the island by Cuban exiles fleeing Castro in the late 1950’s and early 1960’s.
The one exception to the rule about the Keys not being known for beach activities is the lovely Bahia Honda State Park, which has been voted one of the best beaches in America for several years. Being a state park has prevented development, so, aside from pavilions, picnic tables and restrooms, there is nothing but sand, sea, palm trees and wilderness, and it is stunningly beautiful. At the southern end of the park are ruins of the old railroad and Overseas Highway bridge. Bahia Honda State Park has an admission charge which varies by the type of vehicle and the number of people in it. Still, it’s worth the price of admission to see one of America’s best beaches.