During the week before Thanksgiving in 2024, my wife and I took a four-night vacation to Key West, Florida. Neither of us had ever visited the island, which holds an oversized place in the American cultural imagination. Key West has attracted a wide range of celebrities over the years like Ernest Hemingway, Jimmy Buffett, Tennessee Williams, John James Audubon, several U.S. Presidents, and countless movie stars and musicians. Harry S. Truman was so charmed by the place that he had a Little White House there, where he spent 175 days over eleven visits during his administration.
Most people believe that Key West is as far as you can go south and still be in the country, but the true southernmost point of the continental U.S. is Ballast Key located south and west of Key West. Nevertheless, Key West has adopted the “southernmost” tourism brand for itself, complete with a photo-op concrete buoy and numerous locations using the moniker. The southern tip of the island is a mere 81 nautical miles from the north coast of Cuba. We stayed at a lovely property called Southernmost Beach Resort with a balcony room on the third floor overlooking the ocean. The water was rough for our first two days, and it was wonderful listening to the waves crashing against the massive concrete sea wall just below our room.
Running four miles long and about two miles wide, Key West is a very walkable island. We walked the entire width, north on historic Duval Street, which carried us from our resort up to the marinas and cruise ship docks. We wandered around the tourist attractions in that area, including the shops at Mallory Square. We also spent some time strolling through the Old Town historic district, which is filled with beautifully restored 19th century homes, some of which are now bed and breakfast accommodations, although many are still private residences. The following is a list of highlights from our trip to this tropical paradise, which truly exceeded our expectations.
Duval Street: Named for the first territorial governor of Florida, William Pope Duval, this is Key West’s main drag and is filled with shops, restaurants, bars, and vintage hotels that are reminiscent of what I think of as “Old Florida” that flourished during the golden age of tourism in the 1950s and 60s. We walked up and down Duval numerous times for shopping, dining, and drinking (as the locals say, “It’s Key West”).
Hemingway Home and Museum: The author of classics such as The Old Man and the Sea and For Whom the Bell Tolls lived with his wife, Pauline Pfeiffer, in this two-story residence during the 1930s. After eight years of residing at the house, Hemingway moved to Cuba in 1939 and divorced Pauline the following year. Pauline lived in the house until her death in 1951. The only full-time residents now are the famous six-toed cats that lounge around the property, in and outside the house.
Mansion on the Sea: Built in 1897, the iconic Mansion on the Sea, was originally home to Judge Vining Harris and his wife Florida Curry, the youngest daughter of the state’s first millionaire, William Curry. Wanting only the best for his youngest daughter, Curry commissioned Thomas Edison to install the electricity in the one-bedroom home. Over the years, the Mansion evolved and took on many different purposes. During Prohibition (1919-1933) the Mansion served as a destination for many notorious gangsters and other famous travelers. Five U.S. Presidents, including, Harry S. Truman, Dwight D. Eisenhower, John F. Kennedy, Richard M. Nixon, and James E. Carter, Jr. were guests here. The Mansion is now a boutique inn. We had drinks and coconut shrimp at the outside bar the Mansion our first night on the island.
St. Paul’s Episcopal Church: This the fourth building on this site and houses the oldest church in the Florida Diocese. Established in 1832, this oldest U.S. congregation south of St. Augustine has been served by dozens of priests throughout almost two centuries. The church building and grounds at the corner of Duval and Eaton Streets are open daily for prayer, meditation, and visitation.
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