The Best in Key West History and Culture

Even though Key West is small,  a mere 5.27 sq miles in size, there arguably more than a hundred things to do in Key West. The most exciting and most interesting of all the Keys, is the place that literary greats and American presidents made it their home away from home. Key West is isn’t just a  relaxed seaside resort town, it is woven into the greater American cultural fabric with a history all its own. Check out these spots to get your fix.

Tour the Harry S. Truman Little White House

One of the most popular things to do in Key West, is see the 19th century naval station that the 33rd president of the United States, President Harry S. Truman turned into a beautiful vacation home after successfully concluded the Second World War and witnessed the beginning of the Cold War.  History states that he spent 174 days of his leisure time in the exquisite little plantation house. The house later served as a command post during the Bay of Pigs stand-off, and  as a refuge for President Dwight Eisenhower after he suffered his 1956 heart attack. These walls echo with stories, so it is easy to see why it’s one of the most popular things to do in Key West

Visit the Shipwreck Historeum Museum

The history of key west is enlightening while also being interesting. One of the most interesting things to do in Key West is to meander through the Shipwreck Historeum Museum. You will see artifacts from the mid 19th century, taking a trip  through the mysterious period of shipwrecking.  Live actors, props, artifacts, and laser technology, will help you experience the treacherous days of old, and tell you all about how shipwrecking was turned from tragic events to an enterprise of treasure. The  industry was once the only reason Key West prospered, and families became unbelievably rich because of other people’s suffering. This museum experience is a must-see so if you have time, you should enjoy the show.

View The Ernest Hemingway Home & Museum

Hemingway, who was by no way a boring man, wrote seven novels, six short story collections, two non-fiction works, a Pulitzer prize for non-fiction and a Nobel Prize for Literature.  One of the most influential novelists in American literature, and undoubtedly one of the most memorable, Hemingway traveled the world, taking part in some of the most historic moments of his time, so his life was lived to the fullest. A visit to Key West wouldn’t be the same without seeing the sites American writer frequented, or, for that matter, visiting the Hemingway Home & Museum. The halls of this remarkable home ooze masculinity and the descendants of Hemmingway’s original polydactyl cat, Snowball, still live on the grounds. Open 365 days of the year, so be sure to squeeze it in.

There are many more historical things to do in Key West, so if you want to learn more about this unique little island, know that there are plenty more places to learn about history.

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Key West Party Boat Fishing Charter

Our Key West Party Boat Fishing Charter is great for an affordable day on the water with friends and family enjoying the best Key West...

6 hours (approx.)Free Cancellation
6 hours (approx.)Free Cancellation
6 hours (approx.) • Free Cancellation
4.7 (147)
Best Rate
$69.69

Key West 4-Seater Gas Powered Golf Cart Rental
Likely to Sell Out
Likely to Sell Out

Considering a golf cart rental in Key West? Four adults can zip around the island in style on a 4-seater gas-powered EZGO golf cart, and...

3 hours and upFree Cancellation
3 hours and upFree Cancellation
3 hours and up • Free Cancellation
4.9 (1,294)
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Key West Sail, Snorkel, Kayak with Sunset Option
Likely to Sell Out
Top10Top 10 Tour Ranked using exclusive Inside Key West data that may include activity quality, traveler reviews, overall popularity, and availability.
Likely to Sell Out

Enjoy an unforgettable morning or afternoon of sailing, kayaking and snorkeling in the pristine marine wilderness of the Key West National Wildlife Refuge....

4.5 or 6.5 hours (approx.)Free Cancellation
4.5 or 6.5 hours (approx.)Free Cancellation
4.5 or 6.5 hours (approx.) • Free Cancellation
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Key West Backcountry Safari
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Top10Top 10 Tour Ranked using exclusive Inside Key West data that may include activity quality, traveler reviews, overall popularity, and availability.
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Spend an unforgettable day sailing emerald waters, kayaking mangrove-shaded channels and snorkeling coral gardens in an unspoiled marine wilderness....

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4.5 or 6.5 hours (approx.)Free Cancellation
4.5 or 6.5 hours (approx.) • Free Cancellation
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Key West Dolphin Watch & Snorkel
Top10Top 10 Tour Ranked using exclusive Inside Key West data that may include activity quality, traveler reviews, overall popularity, and availability.

Board the Dolphin Watch & Snorkel Cruise Key West for a journey to observe the beauty of Key West dolphins....

3 hours 30 minutes (approx.)Hotel pickup offeredFree Cancellation
3 hours 30 minutes (approx.)Hotel pickup offeredFree Cancellation
3 hours 30 minutes (approx.) • Hotel pickup offered • Free Cancellation
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Miami to Key West Day Trip with Snorkeling
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Top10Top 10 Tour Ranked using exclusive Inside Key West data that may include activity quality, traveler reviews, overall popularity, and availability.
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Take a luxury coach tour from Miami to Key West then cruise out on the emerald waters to enjoy a Key West snorkeling trip on...

6 hours in Key West (approx.)Hotel pickup offeredFree Cancellation
6 hours in Key West (approx.)Hotel pickup offeredFree Cancellation
6 hours in Key West (approx.) • Hotel pickup offered • Free Cancellation
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Key West Snuba® (No Dive Certification Required)

Go Beyond Snorkeling is the closest you can get to scuba diving without being Dive Certified! Go Beyond Snorkeling into new depths for greater durations where you...

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Key West 6 Seater Gas Powered Golf Cart Rental
Likely to Sell Out
Likely to Sell Out

Need a Key West golf cart rental that can get a group of six around the island in fun style? A 6-seater gas-engine EZGO Express...

3 hours and upFree Cancellation
3 hours and upFree Cancellation
3 hours and up • Free Cancellation
4.9 (1,294)
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Key West 8-Seater Gas Powered Golf Cart Rental
Likely to Sell Out
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3 hours and upFree Cancellation
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Key West Split Fishing Charter
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Top10Top 10 Tour Ranked using exclusive Inside Key West data that may include activity quality, traveler reviews, overall popularity, and availability.
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On a Key West Split Fishing Charter, you save by dividing the charter cost between several people. Book your Key West split-charter fishing trip now...

4 or 6 hours (approx.)Free Cancellation
4 or 6 hours (approx.)Free Cancellation
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Key West Deep Sea Fishing Charter
Likely to Sell Out
Top10Top 10 Tour Ranked using exclusive Inside Key West data that may include activity quality, traveler reviews, overall popularity, and availability.
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Experience the thrill of a Key West deep sea fishing adventure on a hunt for trophy game fish with your own Key West fishing charter...

4, 6 or 8 hours (approx.)Free Cancellation
4, 6 or 8 hours (approx.)Free Cancellation
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