Key West, Florida: History, Hemingway Cats, and Gorgeous Water Views

Brian was in Miami for a business trip in 2018, and we decided that was a perfectly good reason to drive all the way down through the Florida Keys to Key West. The drive became part of the fun. Water kept appearing beside us, the islands grew smaller, and the whole trip felt more relaxed with every mile south.

We also tried to see whether we could reenact the bridge scene from True Lies. Unfortunately, the old bridge still had its famous gap. So much for that plan! The movie connection gave us something to laugh about on the drive, but the Overseas Highway really does deserve time of its own. I would not treat it as a transfer to rush through.

Once we reached Key West, our stops were a very us combination: presidential history for both of us, another literary house for me, a famous photo marker, gorgeous water views, and enough food and entertainment choices to make us wonder whether we should have stayed closer to Duval Street.

The Truman Little White House Was an Unexpected Highlight

The Harry S. Truman Little White House was unexpectedly nice. I knew the presidential history would be interesting, but the guided tour was better than I expected, and the tropical grounds made the whole stop feel calm rather than formal or stuffy.

This was Truman’s working retreat in Key West, not simply a vacation house with a famous name attached to it. The tour connected the rooms to the decisions, meetings, and people that passed through them, which made the history feel much more immediate. I would recommend it even to someone who does not normally build a trip around presidential sites.

Current tours take visitors through the former presidential residence in Old Town. Hours, tour formats, and ticket availability can change, so I would check the museum directly before choosing a time.

Hemingway, History, and Six-Toed Cats

The Ernest Hemingway Home and Museum was another one of my literary stops, as Brian would say. I am always interested in the places where writers lived and worked, and this house gave me both the literary history and one of Key West’s most memorable details: the cats.

The six-toed cats were fascinating. They wandered around the property as if they were the true owners of the house, which perhaps they are at this point. The museum says Hemingway was given a white six-toed cat named Snow White and that some of the cats now living on the grounds are her descendants.

Even if the cats get most of the attention, I would still make time for the house itself. Seeing the rooms, gardens, and writing environment together gives the visit much more meaning than simply stopping for a cat photo.

The Southernmost Point, Rain and All

We stopped for the classic photo at the Southernmost Point marker. It was raining, our jackets were on, and the ground was soaked, but that almost makes me like the photo more. It looks like our real trip instead of a perfectly staged Key West advertisement.

This is a quick stop rather than a major experience, and a line can form when Key West is busy. If the photo matters to you, go with patience and do not let a passing shower ruin it. The marker is close enough to the Hemingway Home that the two stops can fit naturally into the same part of the day.

Fort Zachary Taylor Had the Views We Came to Key West For

The views from Fort Zachary Taylor Historic State Park were gorgeous. The water had that clear blue-green color I wanted from Key West, and the palms, rocks, boats, and wide horizon made the park feel like a true break from the busier streets.

The park is not only a beach stop. Fort Taylor predates the Civil War, remained under Union control during the war, and now preserves an important collection of Civil War-era seacoast cannons. That combination worked especially well for us: Brian and I could explore the history, then step outside to some of the most beautiful coastal views of the trip.

Current park information lists swimming, snorkeling, picnicking, fishing, paddling, and fort tours among the options. The fort closes earlier than the wider park, so check the official hours and fees before building the day around it.

Duval Street Gave Us Choices, and Tropic Cinema Gave Us a Break

We walked along Duval Street and had no shortage of food choices. It is lively, colorful, and full of places to eat, drink, shop, and keep the evening going near the water. On another visit, I would seriously consider a hotel in or near this area if nightlife and the freedom to walk between restaurants and entertainment were the priority.

We also caught a movie at Tropic Cinema while we were there. It is not one of the major Key West attractions, and I left it off the map on purpose, but it belongs in our story. Sometimes an air-conditioned movie and a little unscheduled downtime are exactly what a trip needs.

The Dry Tortugas Decision We Still Think About

We seriously considered taking the boat to Dry Tortugas National Park. At the time, the roughly two-hour ride each way made us reluctant, and we decided not to go. That is a substantial amount of boat time for one day, especially if anyone in the group is unsure about motion sickness or being committed to the schedule.

If we went back, we might make a different decision. Dry Tortugas sits about 70 miles west of Key West and is accessible only by boat or seaplane. The pictures of the water, islands, and Fort Jefferson look so serene that the journey now feels less like time lost and more like part of the experience.

I would treat it as its own major day, not something to squeeze around other Key West plans. Compare the ferry and seaplane experience, check the National Park Service guidance, and decide whether the travel time fits your group before committing.

How I Would Plan the Pace Next Time

If my dates were flexible, I would first look for a day when a large cruise ship was not scheduled to be in port. Key West will never be empty, but removing one major source of same-day visitors can make the most popular streets and photo stops feel less congested.

I also like the idea of mixing two different versions of the Keys. One option is to stay near Duval Street for the nightlife, restaurants, and the ability to walk back to the hotel. The other is to choose a much slower-paced hotel farther up the Keys, enjoy the relaxing water views there, and drive down to Key West during the day for the larger range of history, food, and entertainment.

That split would give me what I liked best about this trip: the energy and variety of Key West without giving up the calmer feeling that made the drive through the Keys so appealing in the first place.