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Blog: Six Wonderful Hours in Key West, Florida

June 20, 2025 by Selby Brown |
Hemmingway Kitty

If you’ve booked a Caribbean Cruise there’s a good chance that Key West, Florida may be on your itinerary. According to Cruise Dig, between January and June 2023, there will be over 100 arrivals into the Port of Key West, offering cruisers the opportunity to spend a day with this charming island community. Situated at the farthest west part of the Florida Keys archipelago, Key West is famous for its beaches, nightlife, water-sports, fishing, historic sites, and architecture. Discovered by Ponce de Leon in 1521, the island became part of  the United States in 1822 after Lt. Commander Walter Perry sailed his schooner the USS Shark to the island and planted the United States flag.

My adventure in Key West started post embarkation rush on the Celebrity Silhouette, as the previous evening I’d decided to take a relaxing breakfast in the dining room and enjoy a cappuccino on deck prior to the day beginning in earnest.  My agenda included walking to The Ernest Hemingway House and The Harry S. Truman Little White House, then lunch, and finally shopping.

Less than a mile from the Port of Key West, located at 907 Whitehead street, The Hemingway Home & Museum is open from 9:00a to 5:00p (check for updated hours) and offers cats, tours, and a shop. There are over +50 cats roaming the property grounds and are as much an attraction as are the house and its history. While cats normally have five front toes with four back, a vast majority of the Hemingway cats are six-toed. Decedents of a six-toed cat given to Ernest Hemingway by a ship’s captain, they are adorable, playful, everywhere, and lovingly cared for by the staff. The tour itself is guided  and interesting, starting on the lower level, then winding upstairs into Ernest’s bedroom. Along the way there are personal photos, movie posters, and other paraphernalia to be amused by. The tour ends with a look into the Hemingway writing studio. (The Hemingway Home & Museum, general admission $18, cash only)

A short walk away is the Harry S. Truman Little White House located at 111 Front Street. Remodeled in the 1940s, the house was built in 1890 as navel officer’s housing but later updated in 1911 to a single residence to house the base commander. While the house is best known as a reflection of Harry S. Truman, it has been used by other United States Presidents, namely William Howard Taft (1912), Dwight Eisenhower (1955-1956), John Kennedy (1961-1962), Jimmy Carter (1996, 2007), and Bill Clinton (2005).  Truman, over the course of his Presidency, spent a total of 175 days in the residence and visiting it today is like stepping back into the 1940s as the decor has purposely remained the same, even down to the wallpaper.  Decor aside, the residence’s history is palatable, decisions on the rebuilding of Europe after WWII, issues on Civil Rights, creation of the Department of Defense, changes to foreign policy, and the United States response to the Cold War were made within the building (Museum tour $24.67).

There are some great restaurants in Key West, for lunch I enjoyed the Conch Republic Seafood Company which offers dock-to-dish dishes, I had the Local Fresh Fish of The Day Sandwich (Mahi Mahi) with Swiss cheese and grilled onions. While seemingly a bit touristy, it was lively, excellent, and offered the Key West vibe I was looking for.  The restaurant is located within the old Singleton Fish House and Ice Plant, make sure you look around at salvaged items of historical importance within the restaurant.  After lunch make sure you stop for key lime pie at Kermit's Key West Key Lime Shoppe (335F Duval Street) offering pies, pie bars, juice, cookies, candy, and other items. Afterward, shop alongside the many quaint streets in town but buyer beware, retailers may markup the prices of goods to cover the transaction fees associated with credit card charges.

I’ve included additional pictures from this Day Trip on Facebook. Visit my page as I travel the world sharing experiences, providing travel insights, and opinions.

Fun facts about Key West you might not know: 1) During the mid-1800s, Key West was one of the richest cities in the United States per capita due to industries like wrecking, salving, and salt manufacturing, 2) Pan American Airways (PanAm) was founded here in 1927, 3) Key West closer to Havana, Cuba, than to Miami, 4) Key West's got a chicken problem (and I loved it!), they’re everywhere, if you're afraid of Chickens, don't go.

Happy trails and thank you. Selby
P: 619-846-7322 | E: SVBROWN@dreamvacations.com | Sign up for my Weekly Newsletter for a chance to win a free vacation