Looming over Mallory Square near the Margaritaville Resort & Marina, the Custom House is an iconic Key West institution. An imposing four-story, red brick structure built in 1891, it’s a sight easily recognizable from land and sea. Originally home to Key West’s post office and district courts, today the Custom House is a fascinating museum run by the Key West Art & Historical Society. Their mission is to preserve the culture of the Florida Keys through the exhibition of art, architecture and history to educate the community and visitors.
Many find Key West strange during the day; but after the sun goes down, the restless souls of the island’s frightful past begin to stir. You will hear their tales that have been all but forgotten as you travel the narrow, dark streets of Old Town – filled with 19th century wooden houses that hold on to the secrets of their former inhabitants. Stories so tragic, so chilling, you’ll see why Key West is one of the top ten most haunted cities in America.
This lovely Key West home is where legendary author Ernest Hemingway lived and worked for more than ten years. The home and gardens are visited by thousands of people each year, offering a glimpse into Hemingway’s life and a chance to meet some of the descendants of his beloved six-toed cat, Snowball.
This historic tower was built in 1862 during the Civil War and is one of three remaining Civil War era structures on the island. Although it was often used for target practice by the United States Navy, the fort was never actually involved in a battle. It is now home to the Key West Garden Club.
Key West’s historic seaport has long been a hub of activity on the island. Hundreds of years ago, sea captains found the area a useful and safe stopping point in their journeys. It was the epicenter for industries including sea turtle fisheries, shrimp and sponge fisheries. Today, the area has maintained its charm, with a lovely mix of old and new and offering visitors not only a scenic view but also a variety of unique attractions in the midst of restaurants, shops and activities.
As part of the San Carlos Institute, which was founded in 1871 to help the Cuban community in Key West, the San Carlos Theater offers a variety of entertaining productions throughout the year. It’s the first and oldest theater in Key West, and was once a home to touring ballets, opera and theater companies. Today the San Carlos Theater, after a magnificent restoration, offers concerts and other theatrical events.
The oldest house in South Florida was built in 1829 by Captain Francis Watlington who was, among other things, a wrecker. Watlington and his wife and their seven (of nine) surviving daughters lived in the house for many decades. A beautiful example of the kind of colonial architecture found in the Caribbean, the house is now a museum that welcomes visitors from around the world. Guests see gold that was salvaged from shipwrecks, paintings, model ships and a separate kitchen. Furnishings, carpets and the house décor all reflect the era of the wreckers and their success that made Key West the richest city in America at one time. There’s also a lovely garden with benches offering a shady spot to rest and relax. Learn a little history, admire the ancient architecture and more at the Oldest House Museum.
After seeing some of the city’s most colorful and quirky characters on Duval Street and in Mallory Square, take a moment to visit the Key West Cemetery, where it is said that close to 100,000 original Key Westers are buried. It’s an excursion that offers history, at the bast of lighthearted humor. Located on Solares Hill, which is the highest point of elevation on the island, the cemetery opened in 1847 after bodies from the original cemetery washed ashore during a storm. Stroll through the 19 acres and see if you can find the headstone that reads “I told you I was sick”, or “At least I know Where He’s Sleeping Tonight”.
Key West is famous for being the southernmost city in the continental United States. When you visit, it’s essential that you make it to the southernmost point on the island, found at the intersection of Whitehead Street and South Street. Here, you’ll see the landmark Southernmost Buoy (a required photo opp) and a whole host of other “southernmost” attractions that make for a fun Key West afternoon.
A lasting tribute to the most famous and influential residents of Key West, the Key West Historic Memorial Sculpture Garden is an oasis shared by all who live on the island. Featuring impressive bronze busts of Ernest Hemingway, Asa Tift, Harry S. Truman and others, the garden also includes a scenic walkway paved with memorial bricks that are purchased by local citizens then engraved with their names or the names of a loved one.
Remembering those who were lost to AIDS, the Key West AIDS Memorial is a touching tribute that makes a lasting impression on all who view it. The names of those who have died from AIDS are inscribed on flat granite which makes a walkway on the way to the White Street Pier. It was dedicated on World AIDS Day in December of 1997 and at that time 730 names were included. Sadly, today there are 1,000 names listed on the memorial – all people who lived, visited or worked in Key West. Each year new names will be engraved until the memorial capacity of 1,500 names is reached. The dedication of the new names occurs on World AIDS Day, which is December 1 of every year. A somber site, many come to remember their loved ones, family or friends.
Key West was never a slave port, but in 1860, 3 slave ships headed for Cuba were intercepted by the U.S. Navy. 1,432 slaves who survived the transoceanic voyage were brought to Key West for care. Despite the best attempts by the island’s residents, 295 are buried in shallow graves near the West Martello Fort.
The Audubon House marks the beginning of the restoration movement in Key West. Saved from being demolished in 1958, the 19th century Key West gem is a historic museum featuring the artwork of John James Audubon. Famous for his exquisite drawings of birds in their natural habitat, Audubon stayed in the home in 1832.
The East Martello Fort, complete with an eight-foot thick granite wall, was built during the Civil War Era to withstand any bombardment but was never completed and never saw any hostile action. The casemates, citadel and courtyard today make up the museum. Among its collection are Key West artifacts, historical records and military memorabilia. Also on display are the state’s largest collections of painted wood carvings and drawings by Mario Sanchez. In addition, the fort is also home to Robert the Doll, the most famous haunted plaything in the world.
For a bit of history and a look at how Key West got to where it is today, stop in at the Key West Museum of Art and History inside the Custom House. Built in 1891, the Custom House had many uses including a post office, court house and government center. Today, after a $9 million restoration, the beautiful red brick building is as glorious as it was back in the day and is home to moving works of art that portray the colorful past of Key West and historic national events.
A place where an array of leaders, legendary inventors, dignitaries, visionaries and many prestigious visitors were drawn to throughout its history, Key West’s Harry S. Truman Little White House holds a special place in the history of America. Constructed in 1890 to serve as the naval station’s command headquarters during the Spanish-American War, World War I and World War II, this historic site later became the second White House.
If you’re up for a climb, you’ll be rewarded with stunning views of Key West and the ocean. The Key West Lighthouse was built in 1825 to help the many ships entering the port avoid the hazardous reefs. Today, you can climb the 88 iron steps to the top of the tower for a scenic look at what the lighthouse keepers watched over for more than 120 years. Tour the grounds to see the Keeper’s Quarters which have been restored to their original charm and view the displays of nautical artifacts, antique furnishings, maps and vintage photos.