Best Key West Historic Sites You Must Visit on Vacation

Sitting just under our noses and the mainland United States is Key West, a town teeming with a rich history just waiting to be uncovered. Key West historic sites are some of the most overlooked and fascinating destinations in North America, delivering unique educational experiences to thousands upon thousands of visitors every year. Check out an array of Key West museums that will leave you in awe of your destination and happy you chose Key West history as the theme of your vacation. Eat, drink, let go and learn, all under the beaming Key West sun on your next island getaway.

Top 10 Key West Historic Sites

#1 Sails To Rails Museum

All about Key West history, this Key West museum tells the story of the island through the lens of the evolution of travel. Learn about stories of treacherous pirates in the age of sail as humanity moved forward with steam engines, and eventually the contributions of Henry Flagler and his ambitious overseas railway. The modes by which the American people have spread throughout the continent and the world have always majorly affected history, and Key West history is no exception. Sails To Rails is one of the truly unique historic Key West sites. Enjoy a self-guided tour that allows you to take all the fascinating exhibits in at your own pace.

#2 Ernest Hemingway House and Museum

A truly iconic historic Key West site, the Ernest Hemingway House and Museum is a grand memorial to the Nobel Prize-winning author. Roam the grounds and gaze out on the waters that inspired his masterpiece, The Old Man and the Sea, and pick up a copy in the gift shop. A fine piece of Key West history, the Ernest Hemingway House and Museum is an unparalleled glance into the mind of a literary genius of the 20th century. Count the cats running around the author’s house and take your guess as to which ones are descendants of Hemingway’s very own six-toed feline. “The Sun Also Rises” over historic Key West, and this Key West museum is a can’t miss site for American history and American literature buffs alike.

#3 Truman Little White House Museum

This historic presidential museum is a historic Key West site that played a major role throughout the political career of former president Harry S. Truman. From the G.I. Bill of 1944 to the establishment of NATO in 1949 and much more, the Truman Little White House museum covers it all. Guests of this Key West museum receive an inside look at the contributions of Key West history to events that created the world as we know it today. With multiple tiers of tours available at the Truman Little White House museum, guests can take a casual tour where they receive a fascinating history lesson surrounding the pivotal site, which hosted a number of important government meetings, or enhance the experience with the presidential treatment, including exclusive exhibits and a ride in the former president’s limousine. Book your tour today!

#4 The Key West Lighthouse

Shortly after the establishment of the U.S. naval base in 1823, this historic Key West site was erected to ensure the safe navigation of military and commercial vessels through South Florida’s reef-laden waters. Today, guests of this Key West museum can learn all about the renovations that have been made to the structure over the years and pay homage to the brave men and women who worked through dangerous times to keep the light burning. Walk the 88 steps to the top of this piece of Key West history, gaze out onto the turquoise waters off the Florida Keys and learn all about the lighthouse keeper way of life. All this and more at the Key West Lighthouse.

#5 Fort Zachary Taylor

A former military base that played major roles in the Civil War, the Spanish–American War, World War I, World War II and the Cuban Missile Crisis, Fort Zachary Taylor is a historic state park perfect for tourists seeking all kinds of entertainment. This historic Key West site tells a story of military history as well as architectural history through expert-guided tours of the pivotal structure, situated at the southernmost point of the continental United States. From a presidential namesake to history-altering war games, Fort Zachary Taylor is a piece of Key West history with a fascinating story waiting to be told.

#6 Dry Tortugas National Park

Seventy miles west of Key West is Dry Tortugas National Park, home of Fort Jefferson. This Key West historic site is 100 square miles of mostly open water and is home to an array of Key West wildlife that makes the island and surrounding waters so special. Take any number of ferries or charters to arrive at Dry Tortugas National Park and explore Fort Jefferson before venturing off on one of the many excursions this Key West attraction has to offer. Settle into the popular campgrounds to spend the night amongst the unique ecosystem, and stare up into the star-riddled night sky. This little nest of Key West history lets guests see things the way they were before the effects of humanity — and is a truly stellar experience.

#7 Audubon House & Tropical Gardens

Built in the 1840s, the Audubon House & Tropical Gardens are a historic Key West site that tells the tale of a wealthy family that had roots on the island for over a century. Learn the history of numerous shipwrecks in the reef-riddled waters off the shores of Key West and how Captain John Huling Geiger, builder of the Audubon House, turned it into a fortune and legacy that has lived on. This Key West museum has been restored to its former glory and in the style of its original state, giving guests a glimpse into the past like no other.

#8 Key West Cemetery

In the center of Old Town Key West lies hallowed ground full of Key West history and stories that have built the historic island into the place it is today. Key West Cemetery is a perfect excursion for those tourists looking to get off the beaten path when visiting the island town. Chickens and iguanas roam this Key West historic site, where the tombstones are older than the cemetery itself, as it was reconstructed after being devastated by a hurricane in 1846 that scattered the cadavers throughout a nearby forest. The final resting place of a number of veterans of the Spanish–American War, as well as the 1868 Cuban Revolution, the Key West Cemetery is a place where people from all over come to pay respects. A fascinating property loaded with fascinating stories and pieces of history, a visit to the Key West Cemetery is sure to enhance any visit to Key West tenfold.

#9 Historic Seaport

With a lively roster of events constantly cycling in and out, Key West’s Historic Seaport lives proudly along the Harbor Walk waterfront. The Historic Seaport has served as a global maritime trade base for 200 years and today is home to many of Key West’s can’t miss attractions. With a number of restaurants lined up along the boardwalk, as well as plenty of Key West museums, this sector of historic Key West can be enjoyed by people of all ages. The Historic Seaport is a great place to book your next stay in Key West, with a number of the city’s finest hotels scattered throughout the area. With enough here to fuel a whole week of vacation, Key West’s Historic Seaport is a destination you won’t want to miss.

#10 Fort East Martello Museum

Abandoned after the Civil War, Fort East Martello was restored by the Key West Art & Historical Society in 1950 to become the very first Key West museum. Restored to its original 1860s design, the Fort East Martello Museum is a place where guests can peruse authentic Civil War artifacts, as well as learn about the ghosts of East Martello and stand face to face with the infamous Robert the Doll. Fort East Martello Museum may live in the shadow of Fort Zach, but this historic Key West site is every bit as interesting and essential to Key West history. Find out for yourself on your next trip to historic Key West.

Old Town Key West – Key West’s Historic Neighborhood

During his expedition in search of the Fountain of Youth, Spanish explorer Ponce de León discovered Key West in 1521. It wasn’t until three centuries later that Lt. Commander Matthew C. Perry planted the American flag in Key West’s soil on March 5, 1822, that it was declared part of the United States. Ever since, the island has had a number of booming industries surrounding maritime culture, such as wrecking, turtling, salvaging and salt manufacturing. All of these industries played a major role in making Key West the wealthiest city in the United States in the mid 19th century. Being the southernmost point in the continental United States, the United States military saw the need to defend the surrounding waters, and so Fort Zachary Taylor was built from 1845 to 1866, playing a pivotal role in multiple historical events.

Looking ahead to 1912, famous American industrialist Henry Flagler ushered Key West into the 20th century with the establishment of his overseas railway, which connected Key West to mainland Florida. This railway played a huge part in Florida travel until part of its tracks were destroyed by the Labor Day Hurricane of 1935. Key West did not fade from relevance, however, as former president, Harry S. Truman kept the nation’s eyes on Key West with his presidential second home. Much of his business throughout his political career took place at the Truman Little White House that still stands as an honored Key West museum today. In the 1970s and 80s, the island town saw another boom in popularity thanks to the establishment of Fantasy Fest, a 10-day festival in October, as well as being the birthplace of now world-famous Jimmy Buffett’s Margaritaville restaurant chain. Then, with the famous tongue-in-cheek secession of 1982, leading to the formation of the Conch Republic, Key West was solidified as a world-famous tourist destination for years to come.

The Best Ways to See Old Town Key West

#1 Take a Sightseeing Conch Tour Train

Iconic to Key West, the Conch Tour Train is a classic tour that takes guests to all the quintessential sightseeing locations in Key West. Perfect for families with small children, and everybody else too, the Conch Tour Train is a fantastic way to become acquainted with Old Town Key West.

#2 Fury’s Commotion on the Ocean

A maritime city at its core, what better way to see Key West than by boat — and what better boat than Fury’s Commotion on the Ocean? This sunset sail brought to you by Fury will show you Key West in all of its glory while the sky is glowing with picturesque hues of orange and pink. Your view of Old Town Key West will be something straight out of a postcard.

#3 Walk and Browse on Your Own

A walkable city, Old Town Key West is a great place to see on foot. Tons of attractions are all within walking distance of each other, and what better pace to see a place than your own? Peruse this island town just the way you want to, and become acquainted with the wonders of island time.

#4 Fury’s Bike Rentals

Fury offers bike rentals to those who want to take things at their own pace — faster. Reliable bikes built to take you where you want to go, Fury’s bike rentals will put the wind in your hair and time on your side while touring Old Town Key West.

#5 Fury’s Golf Cart Rentals

While visiting Key West, a car is not only unnecessary and overrated, it’s boring! Change things up with the razor-sharp handling and just flat-out fun golf cart rentals from Fury. Fun to drive and ride, get to see all of Old Town Key West without doors with Fury’s golf cart rentals.

FAQs

What should I not miss among historic Key West sites?

With a myriad of iconic historic Key West sites, it’s difficult to say which attractions are must-sees over others, but the Ernest Hemingway House and Museum, Fort Zachary Taylor Historic State Park and the Dry Tortugas National Park boast some of the best tourist reviews.

What is Key West known for?

For being a pivotal city in the Civil War, being the birthplace of the Margaritaville restaurants, being home to Ernest Hemingway and the second home of President Truman, for beautiful beaches, home to the only living reef in North America and so much more!

What is historic about Key West?

Tales of Key West go back about five centuries since European discovery by Ponce de León in 1521. Since then, the island has had historical significance militarily and culturally that is enshrined throughout many Key West museums.

What is the oldest part of Key West?

Old Town Key West, with its origins tracing back to the expedition of Ponce de León.

What is the oldest house in Key West?

The oldest house in all of South Florida is located at 322 Duval Street in Key West. Today it is the Oldest House Museum.

What are the historic Key West homes?

The Key West historic homes are made up of the Hemingway House and Museum, the Southernmost House Hotel, the Dr. Joseph Y. Porter House, the Truman Little White House, the Richard Peacon House, the Audubon House & Tropical Gardens and the Eduardo H. Gato House.

Who have been the famous residents of Key West throughout history?

Famous residents throughout history include authors such as Shel Silverstein, Judy Blume, Ernest Hemingway and Tennessee Williams. Former United States president, Harry S. Truman, called Key West home, as well as former Major League Baseball player Bronson Arroyo.