Key West has a diverse history as the former home of Calusa Indians, Spanish explorers, English pirates and American presidents and writers; Hemingway wrote there and Audubon painted there. There are also great restaurants, shops, galleries and festivals. My top recommendations of the top things to do and explore include:
Explore the architecture: Key West has over 3,000 wood frame structures that survive from the 19th century and comprise a significant National Register Historic District. The houses in the old town are really outstanding. Today, former dwellings of Cuban cigarmakers and spongers, clapboarded, narrow and shuttered, stand next to more stately Classic Revival mansions. These antique dwellings mirror a multi-cultural legacy of Bahamian, New England, African, Creole and Victorian influences. I love the porches, the colors and the tropical vegetation and flowers. The concentration of historic, antique houses, Old Town’s narrow streets, tucked away lanes and dead-end alleys, the close knit neighbors and the pedestrian scale all remain largely unchanged.
Sunset at Mallory Square: The place to be at sunset with street performers, artists and craft vendors and many tourists in a nightly ritual.
Key West Art/Historical Society: 281 Front Street. Located in the old 1891 Custom House, I enjoyed seeing an exhibition by a local folk artist/carver and walking through the history of Key West on the second floor. The information on Henry Flagler and the building of the Florida East Coast Railroad was outstanding. They also run the Lighthouse and Keepers Quarters nearby and Fort East Martello, a Civil War fort and tower near the airport.
The Hemingway Home & Museum: At 907 Whitehead St., this is the home where Ernest Hemingway lived and wrote for 10 years. Seeing the property is a must when in Key West. You can walk through on your own or take a tour. The house is lovely as are the grounds. Make sure to see the famous six-toed cats that inhabit the house and grounds. The Key West Lighthouse, completed in 1825, is across the street.
Tennessee Williams Museum: In addition to Ernest Hemingway, famed playwright Tennessee Williams “visited and lived in Key West from 1941 until his death in 1983. It is believed that he wrote the final draft of Street Car Named Desire while staying at the La Concha Hotel in Key West in 1947. He established residence here in 1949 and in 1950 bought the house at 1431 Duncan Street that was his home for 34 years.” ” His works such as The Glass Menagerie, A Streetcar Named Desire and Cat on a Hot Tin Roof and many others are classics of the American stage which earned him two Pulitzer Prizes, Tony Awards, the Presidential Medal of Freedom, as well as many other literary awards.” You can visit this small museum at 513 Truman Ave. and “enjoy and learn about Williams’ literary accomplishments and life in Key West through an extensive collection of photographs, first edition plays and books, rare newspaper and magazine articles, videos, a typewriter used by the author while writing in Key West and other artifacts on display.”
Instituto San Carlos: At 516 Duval Street, this is the Cuban Cultural Center with museum, gallery, theater and library. It was founded in 1871 by Cuban exiles who came to Key West to plan the campaign for Cuba’s independence from Spain. This is well-worth a visit if you are a history buff. Cuba and Key West have been closely linked for over 175 years. Cigars were made there and Cuban cuisine had a major influence on local cuisine.
Mel Fisher Maritime Museum: Time permitting, you might enjoy this maritime history museum with featured displays on shipwrecks including the artifacts and treasures from Spanish galleons and the history of slave ships that were captured by the US Navy and brought to Key West.
Harry S. Truman Little White House: This was my favorite historic site in Key West. Beginning in 1946, this became the Winter White House for Truman. He would bring his military and political staff down for meetings and strategy sessions. Here he worked on the Marshall Plan and fired General Douglas MacArthur after WWII. Since I am from Missouri and met Truman when I was in my teens, I was so interested in his history here in Key West including his love of bourbon and playing cards. Following him, many other US Presidents have visited here; JFK had meetings here prior to the Bay of Pigs invasion in Cuba, while Eisenhower, Carter and Clinton have also visited. In 2001, it was the site of the international peace talks between the presidents of Armenia and Azerbaijan. The decor is exactly as Truman would have left it.
Key West Garden Club: The club maintains the gardens at the the West Martello Tower at 1100 Atlantic Boulevard on Higgs Beach. The gardens are scattered throughout the ruins of the old Fort. It is worth visiting to see the beautiful tropical flowers, if you have the time.
Other activities in Key West include snorkeling, sailing, boating, fishing and sunset cruises. You can rent bikes or walk the streets all day like I did in order to walk off the multiple key lime pies I tried!