Key West's Best Selections

At only 2 miles wide and 4 miles long, Key West confirms that good things come in small packages. The two good things in this case are Old Town, the area west of White Street to the Atlantic Ocean and Gulf of Mexico, and New Town, the land east of White Street to Cow Key Channel. 

It was along Old Town's waterfront that Key West sprang to life in the early 1800s as the treasures of the sea lured captains, merchants, and ship salvers. They built wharves, warehouses, stores, and fancy homes, many of which remain today, forming one of the largest collections of pre-Victorian and Victorian buildings in the country. 

Start your walking tour where it all began, at the waterfront. About 175 years ago Mallory square bustled with people conducting business in ticket offices of steamship lines, at wrecker auction warehouses, and with the Navy's anti-pirate unit. Today, the square at the foot of Duval Street is the ultimate place to people-watch. Each evening thousands gather for sunset in a celebration reminiscent of a seventies happening, with street performers, artisans, animals, skaters, bikers, and food vendors. Sharing the nearby waterfront are such attractions as the Key West Aquarium, Clinton Square Market, Sponge Market, Key West Shipwreck Historeum, and Custom House, as well as a stop for the Old Town Trolley and Conch Train. 

Walk down Duval Street, the mile-long pulse of Key West. Today lined with bars, T-shirt shops, dance clubs, restaurants, art galleries, and a parade of eager tourists, Duval Street seldom sleeps. Go back in time at #322, the oldest house in Key West, which is now the Wreckers' Museum. In the 500 block, stop to admire the architecture of the Strand Theatre, where Ripley's Auditorium is located, and the lovely tiles on the San Carlos Opera House. Setting itself apart from the rowdier lower end of Duval, Upper Duval Street, between South and Petronia streets, bills itself as the "Upscale End of Town," where the shopping, dining, and partying are said to be more tasteful. 

Thomas Street, parallel to and two blocks west of Duval, runs through the heart of Bahama Village. Historically inhabited by Bahamians and Cubans of African descent, it's beginning to feel the restoration efforts well underway in the rest of Old Town. Oft visited spots here are the Nelson English House, built in the mid-1800s, and Blue Heaven for breakfast, lunch, or dinner. Hemingway came here to dine, box, and gamble. His house is located one block east on Whitehead Street. 

Farther west, Front Street has President Truman's stately former residence. Now the Harry S. Truman Little White House Museum, it's located on the grounds of Truman Annex, a 103 acre former military parade grounds. 

At the westernmost end of the island, Fort Zachary Taylor, once a Civil War bulwark and now a state park and beach popular with locals, overlooks both the Atlantic Ocean and Gulf of Mexico. Enter through the Southard Street gate of Truman Annex.

East of Duval, tourists have returned to the historic waterfront along Land's End Marina and Key West Bight Marina, which has been revitalized with a food market, boardwalk, shops, bars, and restaurants. Favorites here include the rustic open-air Half Shell Raw Bar for dining, the Schooner Wharf Bar and the Turtle Kraals for dining and late-night carousing, and the Waterfront Market for deli foods, baked goods, and fresh produce. There's no shortage of restaurants in this area. Caroline Street, which runs along the waterfront, claims numerous eateries, including the funky Crab Shack; Pepe's, one of the oldest restaurants in Key West; and PT's Bar and Grill, where locals stop for a game of pool and late-night noshing.

Caroline Street is also home to many fine historic homes, including the Heritage House Museum at #410, once the home of a wealthy British businessman and later owned by a friend of poet Robert Frost, who often visited here; the Milton Curry House at #511, a 22-room mansion; and the Edward Arapian House at #529, the former brick home of a wealthy sponger

Two blocks south and parallel to Caroline Street, Fleming Street holds the moniker of "Guesthouse Row, "due to its numerous small accommodations, many of which are restored historical houses: #410, the Colours Guesthouse, the former home of a wealthy Cuban cigar manufacturer; #600, the elegant Marquesa Hotel, at different times a dry goods, drug, and grocery store; and #414, the Pilot House, built by an attorney who served as a customs inspector

On the southern shore, skimpily clad bodies line the beaches: Fort Taylor, Higgs, Monroe County, and South among them, and signs boast of being the southernmost house, restaurant, bar, store, or whatever. While they argue their claims, there's no mistaking the southernmost point in the Continental United States. It's the large painted concrete marker where tourists take turns having their photos snapped, at the corner of Whitehead and South streets.

Though New Town lacks the historical perspective of Old Town, it is, in true Key West tradition, making its own stories every day.

The Overseas Highway splits as it crosses Cow Key Channel and enters Key West , then continues as U.S. 1 or North Roosevelt Boulevard along the north shore, past the Key West Welcome Center, new shopping centers, chain hotels, fast food eateries, and Palm Avenue, which leads to Charter Boat Row and U.S. Navy facilities.

The southern fork becomes A-1-A or South Roosevelt Boulevard, skirting Houseboat Row, East Martello Tower, chain hotels, Key West International Airport, the salt ponds of Riggs Wildlife Refuge, and Smathers Beach before ending at White Street, at the edge of Old Town

Between the two Roosevelts is the former home of Tennessee Williams, at 1431 Duncan Street, and natural treasures like McCoy Indigenous Park at Atlantic Boulevard and White Street, a garden of native trees; Little Hamaca Park at Government Road off Flagler Avenue, where shallow tidal pools that were used to gather salt now attract birds and fish; and Bay view Park, land deeded by a wealthy Cuban cigar maker as a park with memorials to Jose Marti and soldiers of the Vietnam, Desert Storm, and Civil wars.

Several businesses offer excellent tours with lively narratives of Key West. The Old Town Trolley, (305) 296-6688, operates 90-minute tours in a trackless trolley. You can get on and off at 14 different stops. The Conch Tour Train, (305) 294-5161, offers 90-minute tours in an open-air train.

Sharon Wells of Island City Strolls, (305) 294-8380, publishes the free "Walking and Biking Guide to Historic Key West" and gives personalized walking and biking tours of the island's gardens, architecture, history, or whatever you're interested in. The Historic Florida Keys Preservation Board, (305) 292-6718, publishes a free pamphlet and map to several historic walking tours and leads tours of the cemetery Tuesday and Thursday at 9:30. Writers' Walk is a one-hour guided tour on weekends of the residences of prominent Key West authors, including Hemingway, Frost, and Williams. It's sponsored by the Key West Literary Seminar, (305) 293-9291). The Old Island Restoration Foundation publishes "Pelican Path," a free walking guide to Old Town's history and architecture.