KeyWest Water Adventures

Walking Tours and Historic Sites

Old Town

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 Odditorium 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 White Head and South Street.