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Set on the southernmost point in the continental US, Key West looks and feels as though it should belong in the Bahamas. So you’d be forgiven if you thought you’d just stepped foot in the Caribbean!

A laid back place known for incredible cuisine, fishing, diving, and sunset cruises, Key West sits at the end of a much more colorful “red carpet” of coral keys or small islands that collectively form the Florida Keys.

While many may travel to down a margarita alongside a slice of delicious key lime pie under the shade of palm trees, Key West has an incredibly fascinating history; much of which you can still experience.

Though the island may be small at just around 7 square miles, it’s packed with luxurious hotels and resorts in Key West’s Historic District just steps from the world famous Duval Street.

Today we’ve partnered with Hotels.com to bring you this list of incredibly rich historic sites worth visiting!

Best Historic Sites in Key West

Getting to Key West

Key west RF

Key West’s enticing tropical climate is accessible via direct flights from many major U.S. cities including Dallas, New York, Atlanta, and most major Florida cities just to name a few.

Alternatively, it’s just a 3-hour drive from Miami or 3.5 hours by water if you choose to take the thrilling jet powered catamaran ferry known as the Key West Express which departs from Ft. Myers Beach and Marco Island Florida.

A drive along the beautiful Overseas Highway (US 1) leaving Miami will have you crossing over dozens of scenic bridges and islands until you eventually end your journey at Key West, the crown jewel of the Keys.

Traveling Safely and Responsibly

Whichever way you choose to travel, we urge you to travel safely and responsibly. Driving is the most ideal form of transport for socially distancing, and once you do arrive in Key West, remember to keep at least 6 feet of distance between you and others when exploring, wearing a face mask as much as possible.

We additionally recommend you travel with hand sanitizer and wash your hands on a regular basis, check official websites before your trip for the latest updates on policies, closures and status of local businesses, and it may also be worthwhile booking a hotel with free cancellation in case you need to change your plans at the last minute.

Ultimately, it comes down to keeping your safety and the safety of others in mind at all times. Travel today remains uncertain, but if you are comfortable traveling, please within regulation as any travel is at your own risk.

Brief History of Key West

Key West Pelican RF

Ownership of Florida has changed hands many times over the last several centuries and while a number of native peoples inhabited the mainland, there were few permanent inhabitants in the Florida Keys during this time.

Cubans and Bahamians would visit the Keys to fish, but it wasn’t until Key West was sold to the United States by the Spanish in 1822 that it would begin to become developed.

Once known as Cayo Hueso by the Spanish, Key West would quickly become the United States’ richest city per capita in the 1830s. It went on to become a naval base for the Union Army during the Civil War, and several impressive forts were built.

It wouldn’t be until the early 1900s that Key West was finally connected with mainland Florida. The connection started out as the Overseas Railway but when that was destroyed by a massive hurricane, it was rebuilt as a roadway to be an extension of US 1 in 1938.

When you’ve had enough diving in the Keys for fish and other sealife, dive into Key West’s rich history by checking out the island’s following fascinating historical places.

Old Town

Duval Street Key West RF

The Key West Historic District or Old Town, takes up much of the western side of Key West. The Old Town is home to nearly 200 historic buildings, many of which lie along or in very close proximity to Duval Street.

Six blocks of Duval Street are recognized by the National Register of Historic Places and in addition to the many Spanish styled Victorian mansions, it is also where you’ll find most of Key West’s top bars and restaurants.

Duval Street ends pretty much at Mallory Square, where crowds of people gather nightly to catch the sunset and enjoy delicious bites from street food vendors while watching street performers.

Old Town is littered with structures that date from the mid-1800s to the early 1900s, including the Ernest Hemingway House and Harry S. Truman Little White House which I will discuss more in detail below.

You can also pay a visit to Old Town’s Key West Cemetery where you’ll discover many eccentric tombstones that are often accompanied by comical inscriptions. The cemetery’s dead are joined by the island’s many living iguanas and chickens who roam the grounds.

Hemingway Home and Museum

Hemingway House Key West Florida

One of Key West’s most cherished historic homes is the one that housed legendary American author Ernest Hemingway for nearly 10 years. Built in 1851, it would be another 80 years before Ernest himself would move in after it was purchased by his father-in-law as a wedding gift.

I have always loved Hemingway’s work, so my own personal visit to the house was quite special. When I realized Hemingway had written his iconic short story The Snows of Kilimanjaro at the house, the visit became even more special due to the fact that is where my husband and I first met.

Hemingway’s love life would prove to be much more complicated than ours, having married four different women and enjoying the company of many mistresses during his lifetime.

The home now acts as a museum where visitors can tour the gardens and house which is filled with furnishings collected by Hemingway and his family including his personal library and a 17th century Spanish walnut chest.

The house was the first in Key West to have indoor plumbing and the first to have a pool. Oh, and did I mention the house is overrun with cats that have six toes on their feet?

Known as polydactyl cats, there are dozens of these adorable extra-toed cats roaming around which are descendants of Hemingway’s cats.

Image credit: h gruber (CC BY 2.0) via Flickr

Harry S. Truman Little White House

Harry S Truman Little White House

You’ll find it much easier to tour Key West’s Little White House than the actual White House in Washington D.C.

Offering numerous tours throughout the day, Key West’s Little White House became the winter retreat for U.S. President Harry S. Truman during his time in office. Prior to Truman, the house was visited by President William Howard Taft as well as the great Thomas Edison.

The Little White House was built in 1890 and initially acted as a naval station during several wars including the Spanish-American War and both World Wars. Truman would make roughly a dozen visits to the home to relax and many of his personal belongings are now on display.

After Truman, the house would be visited by other presidents including Dwight D. Eisenhower, John F. Kennedy, and the Clintons.

Image credit: R Boed (CC BY 2.0) via Flickr

Audubon House & Tropical Gardens

Audobon House Key West

This beautiful mid-19th century mansion is named after the great naturalist and painter John James Audubon who created The Birds of America which many claim to be the finest American ornithological works.

While Audubon himself never lived in the home that’s named after him, it is thought he visited the gardens that are part of the property during his visits to Key West.

Audubon is said to have painted more than a dozen new birds for his Birds of America collection while he was here and you can view more than two dozen first-edition Audubon bird paintings in the home during your tour.

The house offers daily tours and is located just a block from Duval Street in Old Town. It was built in the 1840s by Captain John Huling Geiger who was at the time one of the wealthiest men in the Florida Keys due to his very profitable ship wrecking industry.

Image credit: amanderson2 (CC BY 2.0) via Flickr

Key West Lighthouse and Keeper’s Quarters Museum

Key West lighthouse RF

Constructed in the mid-1800s, the Key West Lighthouse allows you to get a great elevated look out over Key West. Situated in Old Town just across from the Hemingway House, visitors can climb nearly 90 steps up the lighthouse to a viewing platform.

Down below, you can tour the old Lighthouse Keeper’s Quarters that have been restored and decked out with old photos and plenty of nautical artifacts.

You’ll learn all there is to know about the lighthouse, like the fact its first keeper was a woman. A female lighthouse keeper was almost unheard of during this period. The lighthouse was eventually decommissioned in 1969.

Fort Zachary Taylor Historic State Park

This historic fort dates back to 1845 and was named after U.S. President Zachary Taylor. The fort played a strategic role in both the Civil War and Spanish-American War.

Open to the public daily from 8AM to 5PM, you can tour the bricked fortress and witness its giant cannons. The fort is said to contain the largest collection of Civil War cannons in the U.S.

While tours of the Fort are only available until 5PM, the park itself remains open until sundown so visitors may catch the sunset. The state park covers over 50 acres and is noted as being the southernmost state park in the country.

The park is home to Key West’s best beach, where you can swim, snorkel, and even fish off the west rock jetty.

Discover Even More History

Fort Jefferson Florida Sunset RF

The places mentioned above are just some of the many historical sites located in Key West. You can also visit the island’s oldest standing house which dates back to 1829 as well as the Fort East Martello Museum which is filled with artifacts relating to the Civil War and early life in the Keys.

You can also arrange to catch the ferry that runs to Fort Jefferson which sits lonely in the Dry Tortugas. The fort is the largest brick masonry structure in the Americas and can be visited via day trips or an overnight camping adventure.

Further afield, there are many other historic sites and museums located on the other nearby Keys including Islamorada and its Keys History & Discovery Center which offers up permanent exhibits that explore the history of the Upper Keys. Islamorada is also home to  the family friendly History of Diving Museum.

When you’ve had enough history, make some of your own by visiting some of the other keys to try some Snuba and explore the underwater world of both John Pennekamp Coral Reef State Park and the Florida Keys National Marine Sanctuary.

Megan is an Australian Journalist and award-winning travel writer who has been blogging since 2007. Her husband Mike is the American naturalist and wildlife photographer behind Waking Up Wild; an online magazine dedicated to opening your eyes to the wonders of the wild & natural world.

Having visited 50+ countries across all seven continents, Megan’s travels focus on cultural immersion, authentic discovery and incredible journeys. She has a strong passion for ecotourism, and aims to promote responsible travel experiences.

    

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