The Florida Keys have long been a magnet for adventure seekers, beach bums, artists, and history lovers alike — and nowhere encapsulates this sun-drenched magic better than Key West. If your idea of a perfect vacation includes learning something new while enjoying ocean breezes and cold drinks, then you’re in for a treat. From 19th-century forts to literary landmarks, Key West is packed with historic treasures waiting to be explored.
And let’s be clear: this isn’t your average dusty-museum kind of history. This is vibrant, eccentric, rum-soaked, and unapologetically oddball storytelling brought to life in pastel colors and tropical flair. While you’re hopping between historic stops, you’ll also want to experience the island’s famously fresh seafood and perhaps even cast a fishing line of your own.
Step into the Past at Fort Zachary Taylor
Let’s start with a heavy hitter: Fort Zachary Taylor Historic State Park, a Civil War-era fort built in the mid-1800s. This fortress of red bricks once protected the southern coastline and played a key role in both the Civil War and Spanish-American War. Wander through its winding corridors, climb up the old walls, and take in panoramic views of the turquoise waters below. Then walk down to the beach for a swim or a quiet nap under the pines. It’s a blend of history and nature you won’t want to miss.
Ernest Hemingway Home & Museum
No trip to Key West would be complete without a visit to the Ernest Hemingway Home and Museum. The legendary writer lived and wrote here during the 1930s, and the Spanish colonial house remains nearly unchanged. You’ll meet dozens of six-toed cats (descendants of Hemingway’s own pets), wander through his lush gardens, and step inside the writing studio where he crafted some of his most famous works. Whether you’re a fan of literature or just enjoy a good story, the Hemingway House is a Key West icon.
Harry S. Truman’s Little White House
Presidential history lovers, take note: Harry S. Truman’s Little White House served as the winter getaway for America’s 33rd president. It’s now a museum where visitors can see the rooms exactly as they were when Truman came down to escape D.C. winters. The site also hosted Eisenhower, Kennedy, and even Bill Clinton. Guided tours reveal not just the political backdrop, but also the personal quirks of a president who played poker and walked the streets like a local.
A Taste of the Sea at Eaton Street
Between historic landmarks, you’ll definitely work up an appetite — and there’s no better place to refuel than Eaton Street Seafood Market. Housed in a lovingly preserved Art Deco building just steps from the Seaport, this local favorite serves up grilled lobster tails, golden crab cakes, and their signature Key West pink shrimp.
Grab a spot at one of the shaded outdoor tables and watch the world go by as you dig into the freshest catch in town. Eaton Street’s seafood is so good, you’ll want to bring some home with you. You can check out their selection of shrimp and have it shipped anywhere in the continental U.S. — a perfect way to extend your island flavor long after your trip ends.
Dive into Local Lore at the Key West Cemetery
Now, this may sound morbid, but trust us: the Key West Cemetery is a must-see. Established in 1847, it’s full of quirky epitaphs, unique architecture, and some true Conch history. Notable residents include sailors, cigar makers, and even a legendary Bahamian voodoo priestess. Don’t miss the famous gravestone that reads, “I told you I was sick.” This is history with a side of island humor.
Custom Fishing Adventures with Seize the Day Charters
Looking to experience Key West the way early settlers and seafarers once did? Get out on the water with Seize the Day Charters. Captain Russ offers personalized fishing trips for all experience levels — from calm inshore waters to deep-sea excursions. You’ll not only enjoy the thrill of the catch, but you’ll also learn about the maritime history of the Keys from a true local expert. Read more about Seize the Day Charters and plan a trip that’s equal parts adventure and education.
Visit the Custom House and Mel Fisher Museum
For those who like their history with a touch of treasure, don’t miss the Mel Fisher Maritime Museum. This fascinating spot tells the story of Fisher’s discovery of the Spanish galleon Nuestra Señora de Atocha, which sank in 1622. The museum is home to gold bars, antique navigational tools, and actual artifacts pulled from the depths of the ocean.
Nearby, the Custom House Museum — with its towering red brick façade — offers rotating exhibits on Key West’s art, politics, and quirky past. Stand on the balcony and imagine the arrival of cigar ships from Cuba and the bustling port town Key West once was.
Soak It All In
What makes Key West special is its layered identity — equal parts paradise, pirate port, presidential retreat, and artist’s muse. Around every corner is a plaque, a statue, or an old building with a story that seems stranger and more delightful than the last. It’s the kind of place where history isn’t just preserved — it’s celebrated with a wink and a margarita.
Whether you’re exploring forts, fishing the reef, or enjoying a fresh seafood meal in a historic building, Key West offers a one-of-a-kind blend of the old and the unforgettable. So pack your sunscreen and your curiosity — and prepare to fall in love with a city where the past is never too far behind. Don’t forget to check out TripAdvisor to save and compare your travel accommodations!