All photos © Robin and Arlene Karpan

Key West combines an island vibe with glorious sunsets, mouth-watering fresh seafood, an usual history, larger-than-life characters, and an independent streak that celebrates its off-beat nature.

Though the island is only two by four miles in size, it’s by far the most famous of the Florida Keys. Key West is closer to Cuba than it is to the Florida mainland, sitting at the end of the Overseas Highway, a remarkable 113-mile road stretching southwest from the Florida mainland, with 42 bridges linking 44 islands.

Key West’s economy today is firmly based on tourism, but it started quite differently. In the 1800s, Key West was among the wealthiest places per capita in the United States. The main industry was salvaging shipwrecks, with the treacherous reefs surrounding the islands proving great for business. Improved navigation eventually put an end to that era.

The island had a lot of influence from Cuba throughout its history, with an odd remnant being a large number of chickens wandering freely everywhere. They were brought from Cuba for cock-fighting, but when that sport was made illegal the chickens were left to fend for themselves. They multiplied and thrived and are now considered just another part of the island’s special ambiance.

Throughout Key West, we see reference to the Conch Republic. In 1982, the US government set up roadblocks to the Keys to check for drug smuggling. The traffic tie-ups were quite disruptive. The mayor of Key West said that since they were treating us like a foreign country, we’ll formally separate and become the independent Conch Republic. They declared independence but immediately surrendered and demanded US foreign aid. This clever publicity stunt helped to end the roadblocks, but it proved so popular that they continue to have annual “independence” celebrations.

Sunset celebration at Mallory Square

Mallory Square on the waterfront has been a commercial and social hub since the 1820s. Today it is famous for a sunset celebration every evening. Iconic personalities such as Mark Twain and naturalist John James Audubon wrote about the wonders of Key West sunsets. It is thought that the idea of a celebration started with famous playwright Tennessee Williams, who once applauded as the sun sank below the horizon.

Things get started in the hour or two leading up to sunset. Depending on the day, there might be live music, comedy acts, jugglers, and assorted performers. Street stalls sell everything from food and drink to tourist knick-knacks.

Hit the open water on boat trips

With water in every direction, it’s not surprising that boat trips are popular. One that we enjoyed was a sunset cruise on the SV Argo Navis, a 75-foot luxury catamaran with sails. Another great trip was Fury’s Key West Dolphin Watch where we had some wonderful close encounters with dolphins in the wild. Rather than duplicate the details here, these trips are covered in our post Fantastic Water Adventures in the Florida Keys.

Hemingway Home and Museum

Key West has attracted a lot of writers and artists over the years, but none loom as large as Ernest Hemingway who lived here in the 1930s. He and his wife Pauline restored a grand Spanish Colonial house dating to 1851.

They added many personal touches to the house, including the Florida Keys’s first in-ground swimming pool. It was so expensive to build that Hemingway pressed a penny into the wet cement, jokingly saying “Here, take the last penny I’ve got.” Visitors are invited to try to find the penny.

You can wander through the house and grounds either on your own or on a guided tour. In the studio he wrote some of his famous books such as A Farewell to Arms and Death in the Afternoon. Rooms throughout the house have exhibits on the writer’s life and work. Another idiosyncrasy is that cats are everywhere – around 60 or so roam freely throughout the property. Hemingway was given a six-toed cat by a ship’s captain and it is believed that many of the cats here today are descendants of that original feline.

Famous Buildings Galore

Historic houses abound, including the Audubon House & Tropical Gardens. The grandiose house was built in the 1840s by a sea Captain, John H. Geiger, who made his fortune in the ship salvaging business. After successive owners, the house eventually deteriorated and was slated for demolition in the 1950s to make way for a gas station.

However, it was saved from the wrecking ball and restored to its former glory. This was the start of a concerted effort to preserve many of Key West’s historic treasures. Today the house is a museum and gallery based on the life and work of famed naturalist and wildlife artist John James Audubon who visited Key West in 1832 to sketch the birds of the Florida Keys.

Some of the many other historic buildings include the “Little White House” where US President Harry S Truman spent a lot of time during his presidency, the Civil War era Fort Zachary Taylor, the Key West Museum of Art & History at the Custom House, Maritime Museum, historic lighthouse, among many others.

A small bar and restaurant has a sign in front indicating that it was the original Pan Am headquarters. For several years, Pan American World Airways was the largest airline in the United States. It got its start here in 1927 when it ran a passenger service between Key West and Havana, Cuba.

Key West Butterfly & Nature Conservatory

The Key West Butterfly & Nature Conservatory features more than 50 species of free-flying butterflies from around the world. The enclosed climate-controlled facility is like a lush tropical rainforest, with a profusion of greenery and flowering plants that butterflies like.

Besides getting close to these kaleidoscopic creatures (don’t be surprised if some land on you), exhibits provide the lowdown on butterfly identification and anything else you might want to know about these winged marvels. Several exotic birds have the run of the place as well, with flamingos usually stealing the show.

Eating and drinking your way through Key West

Not surprisingly, seafood is big throughout the island. Eateries range from fine dining to a wide array of informal spots. At the Half Shell Raw Bar, everyone sits at long picnic tables next to the waterfront. Despite the name, raw offerings are only part of the many dishes. Even more casual is BO’s Fish Wagon. The open-air shack has been described as a place where you don’t need to dust the sand off your feet and fresh food is turned out with zero fuss.

Key lime pie is “the” dessert everywhere in the Keys. They are sold everywhere and each place puts a different spin on it. The most elaborate-looking pies we came across were at Key West’s Blue Heaven restaurant.

Pie is the most famous dish made from the smaller, more flavourful key limes. To discover how else they are used, visit Kermit’s Key Lime Shop where imaginative products range from sauces to jams, cookies, specialty oils, and more.

There’s little danger of going thirsty in Key West. Duval Street in the heart of Old Town has 43 bars alone. The most famous is Sloppy Joe’s which was Ernest Hemingway’s favourite bar. They even have an annual Hemingway look-alike contest.

There’s no bitchin’ about this place, despite the name

If rum is your drink, check out Key West’s First Legal Rum Distillery. The rather odd name harkens back to the bad old days of Prohibition and how this became the first place to make rum legally. Rum has a long tradition in the Keys, mostly as a hotbed for rum-running during Prohibition when booze was smuggled from the Caribbean to supply a thirsty US market.

The distillery’s most popular product is Bad Bitch Rum, named for the notorious Spanish Marie who ran an armada of 15 smuggling ships and had a pirate radio transmitter to send false messages about shipments. She was also infamous for going through several husbands, each of whom mysteriously disappeared once he got too involved in her clandestine businesses.

Bad Bitch Rum is aged in French oak barrels that held Pinot Noir red wine for seven years, giving it hints of caramel from the oak along with tannins. Spanish Marie used red wine a bit differently, watering down the rum so that it went farther. Many rums are aged in barrels that are salt-cured with seawater, adding to the unique flavor.

In 2023, the distillery was named by USA Today as the Best Craft Rum Distillery in the United States. To top it off, they offer free tastings, free tours, and even free mojito-making classes.

Getting to Key West and Getting Around

Most people travel to Key West by driving, and visit other parts of the Florida Keys along the way. While having a car is preferable for most of the islands, Key West is a different matter. It is very congested, with parking being sparse and expensive. The best is to leave your car at your accommodation. Some accommodations, such as where we stayed at the Margaritaville Beach House offer free shuttles to Old Town.

Most of Old Town and the harbour area are walkable. Or you can take the Old Town Trolley hop-on hop-off service that circulates through town and stops near the main attractions. The ticket allows to you ride as much as you like during the day. The ride can also be quite entertaining as the driver relates stories about the island.

If your main destination is Key West itself, and you’re not planning to visit other islands, another option is to fly directly to Key West’s small airport.

Resources

• For a comprehensive look at Key West, plus all of the other fascinating islands, see the Florida Keys Visitor Website.
• Islamorada Island Charm on Photojourneys
• Adventures on the Water in Florida Keys on Photojourneys

SUBSCRIBE to Photojourneys below

Feel free to PIN this post on Key West, Florida