Best Historic Sites in Key West

Best Historic Sites and Cultural Attractions in Key West

For such a tiny U.S. island, Key West has a rich history and has played an important role during numerous events of the Civil War. Its strategic location as the southernmost city in the United States, meant that naval forces and vessels spent significant time docked on the island, while three forts were erected to help protect the U.S. from invasion. On the Dry Tortugas, Fort Jefferson remains the largest masonry structure in the Western Hemisphere while Fort Zachary Taylor and East Martello Museum are also fascinating in their own right. There are many other museums for those interested in history, including the San Carlos Institute which showcases Key West's Cuban heritage, the Earnest Hemingway Home for information about the literary legend, and the Key West Lighthouse and Keepers' Quarters.

For a bite to eat while exploring the past, the Key West Historic Seaport has some of the best happy hour food and drink specials in Florida, plus numerous shops, sailing cruises, and snorkeling tours. Divers can hop on a scuba diving adventure to the Cayman Salvage Master, or visit several other wrecks that met their end in the waters surrounding the island. Back on land, a tour of the Key West Cemetery reveals some interesting characters who once lived on the island, and the Truman Little White House offers an important piece of national history. Here are Key West's 10 best historic sites.


A common misconception travelers have when planning a trip to Key West is that there will be sparkling white-sand beaches - when in fact they are few and far between. Fort Zachary Taylor is one of the exceptions and is blessed with a well-maintained, soft-sand beach with chairs, umbrellas, and water sports equipment for rent. Completed in 1866, the fort played important roles in the Civil War and Spanish-American War and visitors can tour the National Historic Landmark at 11 a.m. daily. This 54-acre state park is also home to several nature trails, a stunning coral reef for snorkelers, picnic tables, and a beachfront café.

Recommended for Historic Sites because: You get a bit of history and fun in the sun when visiting Fort Zachary Taylor.

Local Expert tip: Six days a week you can join in some morning yoga on the beach to start the day off right.

Read more about Fort Zachary Taylor State Park →

Divers will appreciate the 187-foot Cayman Salvage Master, which lies in 70 to 95 of water. In the late '70s and early '80s, the steel-hulled vessel played an important role transporting Cuban refugees during the Mariel boat lift and was later seized by the U.S. government while transporting drugs. She was towed out to sea in 1985 to become a sport fishing attraction when the line snapped prematurely. She sank to the bottom on her side, only to be lifted upright following a hurricane. The wreck is full of marine life including Nassau grouper, reef octopus, hawksbill turtles, and goliath grouper, bar jacks, and silversides.

Recommended for Historic Sites because: Not all historic attractions are above ground! This is one of many underwater treasures surrounding Key West.

Local Expert tip: You'll need an intermediate-level diving certification for this one, Open Water ratings do not permit divers to go this deep.

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Key West has served as a presidential retreat since 1880 when Ulysses S. Grant visited the island. This house belonged to Harry Truman and his wife Bess. Truman reportedly despised living in Washington and viewed this as his sanctuary. Truman spent 175 days of his presidency here from 1946 through 1952, a stressful time where he faced post-World War II reconstruction, and the beginning of the Cold War. High-ranking officials met with Truman here to discuss significant legislation such as the Marshall Plan and his fifth Civil Rights Executive Order. The house has been impeccably restored and is open to the public for tours and special events.

Recommended for Historic Sites because: The home is just as much of an important piece of national history as the monuments in Washington D.C..

Local Expert tip: The presidential bedroom can even be rented for overnight stays.

Read more about Harry S. Truman Little White House →


Just three weeks after arriving in Key West, Ernest Hemingway finished "A Farewell to Arms" and he and his wife fell in love with the island. They built their home in 1851 and it is now a National Historic Landmark. Beautiful gardens blooming with hibiscus and water lilies surround the property, along with a 60-foot swimming pool in the thick of it that is an architectural wonder in itself. The house was the first on the island to have a swimming pool and indoor plumbing. Tours take one half hour and include many anecdotes about the writer and his life on the island. To top it off, numerous cats roam the property - some of which still have the unusual six-toes like Hemingway's original feline friend.

Recommended for Historic Sites because: Although touristy, literary buffs and writers may find a little inspiration in this beautiful home, just like Hemingway did.

Local Expert tip: Take the guided tour which is included in the ticket price. You'll get more out of your experience. Cash only.

Read more about The Ernest Hemingway Home & Museum →

Key West Lighthouse Museum
Photo courtesy of Amber Nolan

Key West's iconic lighthouse was built in 1847 and originally powered by 15 oil lamps that helped guide sailors to the island. Although it no longer serves as a functioning lighthouse, visitors can climb the 88 winding steps to the top for 360-degree views of the city and the ocean. Admission includes entrance to the museum (the former keeper's quarters), where audio and visual recordings are available as well as glass display cases of the previous owner's possessions. Photographs and quotes from lighthouse keepers and their families show ensure that the now obsolete way of life will never be forgotten.

Recommended for Historic Sites because: While many lighthouses in the U.S. are not open to the public, Key West's tower invites visitors to explore and learn about the past.

Local Expert tip: Note that it closes at 4:30p.m., so don't try to wait for the sunset.

Read more about Key West Lighthouse Museum →

About 70 miles from Key West lie the Dry Tortugas National Park, seven islands that straddle the Gulf of Mexico, Caribbean Sea, and Atlantic Ocean. Shallow waters surrounding the islands are the resting place of numerous shipwrecks. The challenge is getting there. Most tourists take the seaplane or ferry across - and they aren't cheap. A half-day trip by plane runs $329 per adult, but offers a bird's eye view of the stunning islands. The Yankee Freedom II is only ferry to the park, starting from $175, which covers entrance, meals, snorkeling, and tour of Fort Jefferson. The Fort itself held numerous Civil War prisoners, including Samuel Mudd - the doctor who assisted John Wilkes Booth after his injury.

Recommended for Historic Sites because: A lesser-know historical wonder, Fort Jefferson is the largest masonry structure in the Americas.

Local Expert tip: Visit the Dry Tortugas Park website for rules, regulations, and what to bring.

Read more about Dry Tortugas National Park →

Nowhere is Key West's lively spirit more evident than in the city's cemetery. Cheeky epitaphs like "I Told You I Was Sick" and "At Least I Know Where He's Sleeping Tonight" cover the gravestones.The tombs are stacked above ground since the rocky soil made digging down impossible. Explore and see what you uncover. The main entrance offers a map that details some of the more interesting plots, and an unusual amount of the tomb stones detail information about the deceased life. Go early in the morning or you'll be facing the scorching southern sun "dead on" in the afternoon. Online brochures are also available for those interested in planning ahead. Avoid at night.

Recommended for Historic Sites because: Numerous stones date back to the 1800s and showcase Key West's melting pot of cultures and quirky residents.

Local Expert tip: Grab-rubbing normally makes for great souvenirs, but it is a hefty $500 fine in Key West.

Read more about Key West Cemetery →

Back in the late 1700s, the Key West Historic Seaport had a safe anchorage and stocks of drinkable water at primitive wells ashore. Settlers of the island relied heavily on marine life as an integral part of the economy, including fisheries for sea turtles, sponges, and shrimp to supply local and distant markets. Today, the only turtles you'll see on land are at the Turtle Kraals restaurant, where visitors can witness the turtle races on Mondays and Friday evenings. The rest of the harbor is lined with shops, bars, fishing and sailing vessels, dive boats, and traditional schooners that offer sunset cruises.

Recommended for Historic Sites because: The seaport remains an authentic slice of "Old Key West."

Local Expert tip: There are some excellent Happy Hour spots along the seaport for those dining on a budget.

Read more about Historic Seaport at Key West Bight →

This structure was constructed in 1862 to protect Fort Zachary Taylor from confederate attack. Now it is an eclectic museum that houses various artifacts from Keys life and history. See found art sculptures by Stanley Papio, woodcarvings by Cuban folk artist Mario Sanchez, a Cuban refugee raft and books by the seven Pulitzer Prize-winning authors that have lived in Key West. Be sure to take in the panoramic view from the tower. The legendary Robert the Doll is also on display at the museum, a real life "Chucky" doll that is said to have a life force of its own.

Recommended for Historic Sites because: Fort East Martello offers a glimpse into the Civil War era when many citizens sided with the Confederacy.

Local Expert tip: You can visit the spooky fort after dark to see Robert at night!

Read more about East Martello Museum and Gallery →

The San Carlos Institute was founded in 1871 by Cuban exiles of Key West as an educational, civic, and patriotic center, and now serves as a museum, library, art gallery, theater, and school. The museum played in important role in Cuba's history when, in 1892, legendary patriot José Martí addressed gathering at San Carlos and announced that a united front would be established to lead the effort for Cuba's independence. Exhibits include the life of Marti, a collection of postcards from Cuba, a study on their aviation history, presidents, and more. A small theater also showcases musicians and actors from the Waterfront Playhouse. Be sure to check out the events schedule.

Recommended for Historic Sites because: Cuba has played an important role in Key West's history and this is one place where visitors can learn about it.

Local Expert tip: It is free to enter but they are closed on Monday.

Read more about San Carlos Institute →


Meet Amber Nolan

Originally from upstate New York, this restless traveler has a knack for befriending interesting characters. You can usually find her just about anywhere that has a hammock. Amber's favorite...  More About Amber