In late February 2025, Chad and I set off for a long-awaited getaway to Key West — a trip tailor-made for two Hemingway fans who share a love of history, seafood, and the kind of offbeat adventures that always seem to find us.

We began by flying into Miami and renting a car so we could make the famous drive along the Overseas Highway — that mesmerizing “water highway” linking the Florida Keys by a ribbon of bridges over endless blue. The drive was pure joy: windows down, salt air whipping through, and the sea stretching out on both sides. Along the way, we stopped in Key Largo for lunch at Lorelei’s, a laid-back waterfront spot serving up seafood so fresh it practically winked at us. The view, the breeze, and a perfectly grilled mahi sandwich made it the ideal start to our adventure.

By the time we reached Key West, we were ready to slow down. We checked into The Duval House Bed & Breakfast, a cozy hideaway right on Duval Street but somehow worlds away once you stepped inside. The gardens were lush, the rooms charming, and the staff warm and welcoming. We soon discovered that we wouldn’t be needing our rental car again — everything in Key West was within easy walking distance, which suited us perfectly.

Naturally, our first stop was the Ernest Hemingway Home and Museum. Standing in Hemingway’s writing studio surrounded by his books, artifacts, and a few dozen famously six-toed cats, we felt like we’d stepped straight into his world. Right across the street stood the Key West Lighthouse, and while the climb to the top left me a bit dizzy with vertigo, the sweeping views of the island and ocean were unforgettable.

Our love of history also led us to Harry Truman’s Little White House, where we learned how Truman conducted affairs of state from this unassuming tropical retreat. It was fascinating to see how Key West’s tranquil charm coexisted with such pivotal moments in history.

For a bit of adventure, we booked a snorkeling excursion with Fury Water Adventures. The day was bright and breezy — maybe too breezy for Chad’s liking. After a few minutes in the choppy water, he decided his snorkeling experience was better continued from the boat deck, while I happily stayed in for nearly another hour, surrounded by colorful fish and coral!

Evenings in Key West were their own kind of magic. We spent several nights strolling along Duval Street, ducking into art galleries, quirky shops, and of course, a few of the legendary bars. Sloppy Joe’s, once Hemingway’s favorite watering hole, was a must-stop, as was The Green Parrot, where live music and laughter spilled out onto the street.

One night, we treated ourselves to a delicious seafood dinner at the Conch Republic Seafood Company, a lively harbor-front restaurant where the catch of the day came straight off the boats. The conch fritters and grilled grouper were fantastic, and the view of the marina at sunset couldn’t have been better.

Mornings in Key West were just as enjoyable. We had a leisurely breakfast at Banana Café, where the crepes were delightful and the wild roosters strutted around our table with their hens, completely unbothered by the diners. It was impossible not to laugh at their self-importance — a true Key West moment. Another morning, we discovered Sarabeth’s, a charming spot tucked in a quiet neighborhood, serving some of the best French toast and fresh-squeezed juice we’ve ever had.

On one of our final days, we took a peaceful walk through the Key West Cemetery — a surprisingly fascinating stop filled with quirky, humorous epitaphs like “I told you I was sick.” It was a reminder that the island’s famous sense of humor runs deep, even into eternity.

By the end of the week, we’d seen, tasted, and laughed our way through Key West — from the literary landmarks to the snorkeling reefs, from the bars of Duval to the roosters under the breakfast tables. It was the perfect mix of history, adventure, and relaxation, wrapped in the island’s unmistakable charm.

For two Hemingway fans seeking both stories and sunshine, Key West delivered all of it — and then some.