Culture + Style

Get Schooled on Key West’s Historical Sights

Ernest Hemingway House in Key West, Fla. (Photo: Robert Hoetink / Alamy)

Boozy bar crawls down Duval Street draw tourists galore to the Conch Republic. But Key West offers a rich legacy of history and culture beyond the beer-soaked streets.

Whether you’re visiting the former home of a Pulitzer Prize-winning author, or the site of military shipping routes, Key West offers adventures rooted in history.

key west attractions fort jefferson
Sunset over Fort Jefferson in Dry Tortugas National Park. (Photo: Lee Rentz / Alamy)

Sightseeing at the Tip of the Nation

The Dry Tortugas: The very name conjures images of clipper ships sailing to the ends of the earth. Located approximately 70 miles west of Key West, Dry Tortugas National Park is accessible solely via boat or seaplane.

Whether you motor over via water or air, stock plenty of sunscreen and prepare yourself for a day of exploring Fort Jefferson. Constructed using 16 million bricks, it’s the largest all-masonry fort built in the U.S.

The structure essentially encircles the island, although technically it was never completed. Park rangers and service operators offer guided tours.

As you walk down the long casemates, you’ll hear the echoes of the past. Dr. Samuel Mudd was a prisoner here after the Lincoln assassination.

After touring the fort, consider snorkeling in the clear Key West waters surrounding the island. Visitors can’t swim in the moat encircling the fort, but the water around it is filled with abundant sea life, ideal for sightseeing.

The moat contains one endangered American crocodile, thought to have arrived here because of a storm.

Many Key West accommodations have shuttles that run near the ferry terminal. Check with your hotel to confirm transportation to historical sites.

key west attractions hemingway house cats
Hemingway House cat. (Photo: Bjorn Grotting / Alamy)

Pet Papa’s Cats at the Hemingway House

Literary fans celebrate Ernest Hemingway’s accessible voice and pared-down style. Critics sniff that there’s little point in critical commentary.

No matter which side you champion, a visit to The Ernest Hemingway Home & Museum takes you back to the halcyon days of the 1930s and lets you look into the life of Hemingway.

The house, originally built in 1851, was Pauline and Papa’s home from 1931 to 1940. When they purchased it in 1931, the Spanish Colonial structure was considered a ruin. They restored it and built the first swimming pool in the Keys.

Look carefully to spot the penny between the flagstones that Hemingway reportedly placed, declaring that the pool cost his last cent.

Papa apparently loved cats, and many of the museum’s nearly four dozen cats, themselves prominent among Key West attractions, have six toes. When you spot one snoozing on the 19th-century settee or the white chenille bedspread, take a closer look at their paws.

key west attractions diving
Diving a sunken ship in Key West can be a treasure. (Photo: National Geographic Creative / Alamy)

Wreck Diving into Key West Attractions

If lounging by your hotel’s beachside pool doesn’t offer enough action, how about diving a sunken ship?

The USNS Gen. Hoyt S. Vandenberg, a missile-tracking ship, was sunk in 2009 to become an artificial reef. It rests in nearly 150 feet of water in the Florida Keys National Marine Sanctuary, about seven miles from Key West.

Wreck diving has its own challenges, but the Vandenberg lures divers of all skill levels with its abundant sea life, like sailfish and barracuda. Other cool features include Russian signage from its stint as a Russian science vessel for the 1999 film Virus.