There’s no place quite as “ultimate” as Key West, with its rich literary history, Duval Street “pub crawl” and nightly sunset celebrations.

Nicknamed the “Conch Republic,” Key West was an island unto itself until 1912, when Henry Flagler’s Overseas Rail-
road linked the southernmost city to the Florida mainland.

Museums and Historical Venues

I’ve never counted them, however the dozens of six-toed cats at the Ernest Hemingway Home & Museum are enough to draw in the curious. The house itself is a timepiece to Hemingway with desk, chair and typewriter in the writing room.

A few blocks away, U.S. President Harry S. Truman—the man who ended World War II with a nuclear bomb—vacationed at The Little White House in Key West, held Hawaiian shirt-themed dinner parties, and sunbathed on the beach at Fort Zachary Taylor Historic State Park with a phone on a table at his side. (That was one long phone cord!)

Once the richest city in the U.S. built on the wrecking industry, several of the original warehouses that stored the shipwrecked loot still stand, including one showcasing the Shipwreck Museum where costumed and in-character staff members guide you through the three-storey attraction. On the roof, you can get a bird’s-eye view of the city and ocean from the 19.8-metre lookout tower.

Board the Conch Tour Train, a 90-minute hop-on-hop-off narrated tour of the entire city. It sounds touristy, but believe me, you will learn and see more than if you drive around on your own. Plus, you can simply hop off when a shop or bar lures you away.

Favourite Pastimes

Whenever we are lucky enough to wake up in Key West, we invariably head to the Blue Heaven restaurant on Thomas Street for breakfast. Here, Key West’s famous and protected chickens roam an outdoor dining area and Bloody Marys are made by the bucketful.

We’re paddlers, so we never tire of seeing the city from the seat of our kayaks, either on a two-hour trip into the Key West salt ponds near the airport, or on a daylong 19-kilometre circumnavigation of the island. Either way, Lazy Dog Outfitters on Stock Island can set you up.

Our day almost always ends at Mallory Square toasting the famous sunset celebration where cats jump through hoops, unicyclists juggle sabres, while the Disney set depart on their cruise ships. (Tip: bring some cash to tip the performers or they just might heckle you.)

As the sun sets, the merriment is just beginning in this city of more than 300 bars, including the clothing-optional Garden of Eden. Our favourite stop is the pet-friendly Schooner Wharf Bar, where we can bring our pup and watch tall ships come and go on sunset and sightseeing cruises.

Travel Planner

For more information on Key West, visit fla-keys.com/keywest or call 1-800-527-8539.