At the far end of the Overseas Highway, and at the southernmost points of the continental United States is an island and city unlike anywhere else in the country.
The modern history of Key West begins in the early 19th century. The Florida Keys had long been a graveyard for overladen and misguided ships.
Their wrecks became the lifeblood of a whole industry, with ‘wreckers’ salvaging treasure and other materials from these lost vessels.
Today, Key West means watersports, good times, and the most beautiful sunsets I’ve ever witnessed. Duval Street meanwhile is without question one of the best places to go out in America.
You can use Key West as a launchpad for diving adventures. This is the off ramp for the paradisiacal Dry Tortugas National Park, while a huge artificial reef is just offshore.
1. Mallory Square
Key West’s social life has revolved around this waterfront plaza for more than 200 years now. Where the townsfolk congregated to share the news and do some shopping is an inimitable attraction.
Mallory Square is the venue for the Sunset Celebration, taking place 365 days a year. I would argue that there are few better ways to watch the sun go down.
The crowds arrive two hours before sunset. As the sun sinks over the Gulf of Mexico you can shop for arts & crafts, grab a bite to eat, and watch skilled street performers.
You can take a whirlwind tour of Key West history at the Memorial Sculpture Garden. Here some important local personalities are commemorated with busts. There’s also a monument to the Wreckers, who settled the island in the early 19th century.
2. The Ernest Hemingway Home and Museum
The Ernest Hemingway Home and Museum on Whitehead Street is the city’s most visited paid attraction. Hemingway lived here with his wife Pauline Pfeiffer from 1931 to 1939.
In the French Colonial style, the house dates back to 1851, and it was here that he wrote a number of famous short stories and works of nonfiction. Among them were Green Hills of Africa (1935), and The Snows of Kilimanjaro (1936).
The home is still full of many of Hemingway’s possessions. Most exciting for me is the intact writing room, which you can view through a screen.
Also remarkable are the cats roaming the grounds. These are polydactyl, and are claimed to have descended from the writer’s famous six-toed cat, Snow White.
3. Fort Zachary Taylor State Historic Park
The southern tip of Key West, and the continental United States, is defended by a Civil War-era fort. This installation was begun in 1845, well before the conflict, and was active in both the Civil War and the Spanish-American War (1898).
The fort’s corridors are well worth exploring. The gun ports are still armed with what may be the largest collection of Civil War cannons in the country.
Further south is a small pebbly beach. The appeal of this spot lies in the waters, which are calm, clear and perfect for snorkeling. To get the best out of the beach I’d bring a pair of water shoes.
4. Duval Street
Downtown Key West’s main drag is a 1.25-mile street at the nerve center of the city’s nightlife. One of many cool things I want to share about Duval Street is that it takes you from the Gulf of Mexico in the north to the Atlantic Ocean in the south.
The street’s boisterous reputation comes from an almost absurd concentration of bars. Supposedly, there are more night spots here per capita than anywhere else in the United States.
At the last count there were 43 bars. If, by some miracle, you manage to drink at all of them, you will have completed the Duval Crawl. Naturally, this isn’t a challenge to be attempted in one night.
5. The Harry S. Truman Little White House
Back in the late 19th century, Key West was home to a naval station that played a significant role in the Spanish American War. Just after World War II ended, the building became the winter retreat of Harry Truman.
Eventually he would spend 175 days of his presidency at his winter White House. I was thrilled to learn that subsequent presidents also used the building. For instance, Eisenhower came here to recuperate from a heart attack.
Later, JFK held a summit with Harold MacMilland in 1961, and returned in 1962 in the aftermath of the Cuban Missile Crisis.
The property has been a State Historic Site and museum since 1991. The tour gives you a real inside scoop, with a lot of funny anecdotes. I must admit I got shivers when I saw ‘The Buck Stops Here’ at Truman’s desk.
6. Key West Butterfly and Nature Conservatory
If you’re visiting Key West with children, I think it’s a great idea to keep this spot in your plans. Perfect for a rainy day, the Key West Butterfly & Nature Conservatory is a climate-controlled environment with more than 60 butterfly species from around the world.
Here kaleidoscopic butterflies fly freely among rainforest plants and flowers. They share this glass-domed environment with more than 20 bird species, turtles, and a pair of beautiful flamingos.
To get you started there’s a 15-minute video explaining butterflies’ lifecycle and detailing interesting facts about the various species. At the Learning Center you can find out more about their anatomy, and see where in the world the conservatory’s butterflies come from.
7. Southernmost Point of the Continental USA
One image that springs to people’s minds when they think of Key West is the concrete buoy on the seawall. At the corner of Whitehead and South streets, this monument was erected in 1983 and is a classic photo op.
A quick look at the map will tell you that there’s a more southerly point at Fort Zachary. This is open to the public, while the actual southernmost point is on nearby United States Navy property and inaccessible.
As with all places on this side of Key West, my ideal time to come is when the sun goes down.
8. Mel Fisher Maritime Museum
The Key West resident Mel Fisher was a noted treasure hunter who discovered several shipwrecks in Florida’s waters. His biggest haul came in 1985 with the Spanish galleon, Nuestra Señora de Atocha.
In an historic storehouse from 1910, you can visit a museum dedicated to Fisher’s career and the region’s maritime heritage. I was gripped by the exhibit on his 16-year search for the Atocha.
You can also pore over a trove of neatly presented artifacts recovered from the deep. These include cannons, liturgical items, jewelry, gold bars, coins, pottery, rifles, pistols, and much more besides.
On a poignant note, there’s a rich exhibit on the Henrietta Marie, a slave ship that sank in 1700 and was excavated in the 1980s.
9. U.S. Coast Guard Cutter Ingham Museum
Appearing in many sunset photos at Truman Waterfront Park, there’s a WWII-era Coast Guard cutter preserved as a museum ship.
The USCGC Ingham was in service from 1936 to 1985, and was active during World War II. In 1942, during one of many escort missions, this ship sank the German submarine U-626.
On a self-guided visit you can go where you please, from the galley to the officer’s quarters. All the way you’ll see preserved items, such as uniforms, radio equipment, period furniture, weapons, and even a barber’s chair.
My one word of advice is to be prepared for some steep climbs and descents on your tour.
10. Key West Garden Club
A beautiful oasis by the water, this spot has ocean views and lush tropical gardens, mingling with a Civil War-era fort.
Unlike many local attractions, the Garden Club is free to visit. In addition to its tranquility and photo-ops, it’s full of history, going back to 1863.
I loved the butterfly garden, waterfall garden, fragrant perfume garden, and the various orchid areas. Occasionally you’ll be treated to breezes blowing off the Atlantic.
The ruins of the fort, with vaulted ceilings and gun mounts, bring romance and mystery to this unique place.
11. Dry Tortugas National Park
Key West is the springboard for the marvelous Tortugas Islands. Almost 70 miles to the west, these are the most remote and undisturbed of the Florida Keys.
They are protected by a 65,000-acre national park, only 1% of which is made up of land. As far as I’m concerned, the best way to discover this diving and snorkeling paradise is with your own boat.
This is obviously not an option for most people. So, a couple of alternatives are seaplane charters and the high-speed Yankee Freedom Ferry.
On land, the symbol for the national park is the vast Fort Jefferson. Completed in 1861 and spread across 16 acres, this is the largest brick masonry structure in the Americas. From 1865 the fort was a prison for several co-conspirators in the Lincoln assassination.
12. Sloppy Joe’s
Surely Key West’s most iconic bar, Sloppy’s Joe’s has been a favorite haunt of The Conch Republic since 1937.
In the early days it was a favorite drinking destination for the notoriously hard-living Ernest Hemingway and his cohorts.
Sloppy Joe’s remains a raucous nightspot, with constant live music, wacky special events, and a full food menu. Two essential menu items are the conch fritters, and, of course, the key lime pie.
If you’re in Key West in July, you have to come for the Hemingway Lookalike Contest. This event has been a Key West tradition for more than 40 years now.
13. Florida Keys Eco-Discovery Center
This exceptional visitor center is devoted to the astonishing biodiversity of the Florida Keys National Marine Sanctuary. An immense property, it encompasses the continental United States’ only coral barrier reef.
Some of my favorite exhibits at the Florida Keys Eco-Discovery Center were live feed from a coral reef, a replica of the Aquarius underwater laboratory, and an interactive map of the Florida keys.
You can also survey the 2,000+ ships that have been wrecked in the keys. These are accompanied by images of the artifacts recovered from them.
I was also spellbound by the interactive mangrove exhibit. Here you can test your animal ID skills, working out the calls of this habitat’s colorful residents.
14. Audubon House and Tropical Gardens
From the first decades of the 19th century, this house was built for Key West’s first harbor pilot, Captain John Huling Geiger.
What makes this place significant is the famed painter and ornithologist John James Audubon (1785-1851), who stayed here in the 1830s.
Attracted by the tropical vegetation all around, he composed several works in the house and gardens. Audubon also took cuttings from the gardens, and used them in many of his paintings.
Following hurricane damage, the house was rebuilt in the Classical Revival style in the 1840s. After being slated for demolition, the building became the first of many restoration projects in Key West.
One fact I picked up is that the frame was built from Dade County pine, which is now extinct. This wood was renowned for being resistant to decay and impervious to termites.
On the property is a gallery where you can purchase prints of Audubon’s paintings.
15. The Vandenberg
Source: Peter Leahy / shutterstock
The Vandenberg was an obsolete Navy ship that was sunk off the Key West coast in 2009 to become part of an artificial reef. This has since become home to an amazing variety of marine life, including sailfish and Goliath grouper.
Launched in 1943, the USNS General Hoyt S. Vandenberg served as a troop transport and missile-tracking ship.
Measuring 522 feet, this vessel now lies in about 150 feet of water in the Florida Keys National Marine Sanctuary, about eight miles offshore.
A host of tour and dive options are available from Key West. This is an advanced deep dive, so you’ll need an Advanced Open Water certification. Without this qualification, you can only visit in the company of a private guide.