From Hemingway to Key Lime Pie: Soaking Up Key West

In September 2023, we finally made our way down to the southernmost point of the continental United States for a much-needed getaway to Key West. We hopped on a Southwest flight, and as soon as we stepped off the plane, I knew we weren’t in Kansas anymore. The airport was tiny—like something out of a small mountain town—but instead of pine trees, there was turquoise water just beyond the runway. Right away, Key West had a way of saying, “slow down, you’re on island time now.”

We checked into the Heron House, a charming little inn with porch swings, palm trees, and the constant buzz of scooters zipping by. It was the perfect base to explore the island.

We went full tourist mode right away: the Ernest Hemingway House, where we met his famous six-toed cats and pictured him hammering out novels on that old typewriter, the Truman Little White House, where history somehow felt casual, and the Mel Fisher Maritime Museum, where treasure—literal gold and emeralds—sat in glass cases like it was no big deal. We also wandered through the Key West Museum of Art and History, which filled in the colorful backstory of the island’s characters.

And because a vacation without rum isn’t a vacation, we toured the Key West Distillery and sampled their small-batch spirits. Smooth, tropical, dangerously easy to drink—it was like sunshine in a glass. Fun fact we picked up along the way: all of Key West’s fresh drinking water is piped in from southern Florida. On a tiny island, even the basics are an adventure.

Speaking of drinks—wow. Every bar, from Sloppy Joe’s to the quirky No Name Pub to the countless stops along Duval Street, served cocktails that were both strong and delicious. Combine that with live music, rainbow flags, drag shows, and street performers, and Duval felt like a block-by-block festival of Key West’s diversity and wild spirit.

One unexpected moment of nostalgia came when I spotted an old number sign that I hadn’t seen since I was a kid eating at Country Cook’n restaurant in Harrisonburg, Virginia. I had to stop and snap a photo. At first, I couldn’t place why it felt so familiar, but then the memory clicked—and suddenly I was ten years old again, sitting at a booth with family. It’s funny how travel has a way of pulling memories out of hiding.

The sign from Country Cook'n

We tried (and failed) to get a table at the cheeky dessert spot Better Than Sex, but the attempt was half the fun. We made up for it with key lime pie—and let me say, it was as good as pie gets. Tart, creamy, and unforgettable.

Not every highlight was in town. We drove out to see the tiny, endangered Key deer, which honestly looked like something out of a storybook. And while we wanted to visit Dry Tortugas National Park, we learned those tours book out six months in advance—so that’s officially on our “next time” list.

We wrapped up with a classic sunset at Mallory Square, surrounded by performers and travelers cheering as the sun melted into the Gulf of Mexico. Of course, we grabbed our obligatory photo at the Southernmost Point buoy.

All in all, Key West was everything you’d expect and more—quirky, historic, a little wild, and full of surprises. Between the six-toed cats, treasure hunts, rum tastings, strong drinks, pie, sunsets, and even a childhood memory from Harrisonburg resurfacing, it’s the kind of place that leaves you smiling and already plotting a return.

Go in the fall, outside of the heat and hurricane season.

For more inspiration and insider recommendations, visit our Key West page.