Sunset in Key West, as viewed from Danger Charters' Wind and Wine Cruise — Photo courtesy of Claudia Miller
On your first visit to Key West, you’ll most likely be directed to Duval Street - the mile-long road that bisects historic Old Town - by everyone you meet. If you’re mainly looking for your lost shaker of salt, look no further than the string of bars like Sloppy Joe’s, Hog’s Breath and Irish Kevin’s for a bar hopping experience called the “Duval Crawl.” But if you’re visiting to discover the true Key West with its rich history, marine wildlife, boutiques, art galleries, architecture and sunset sails, then follow this itinerary for a quick immersion experience. You’ll find that one day isn't nearly enough.
Get an early start to your day with the Conch Tour Train, a 90-minute ride through Old Town. While it may seem a little touristy, it’s an informative introduction to the island and an easy way to see over 100 notable points of interest like the Southernmost Point, Southernmost House and Fort East Martello. Their knowledgeable “engineers” share the stories of the pirates, wreckers, Cuban cigar-makers, artists, writers and rumrunners who shaped Key West.
The Conch Tour Train in Key West — Photo courtesy of Bob Krist / Florida Keys News Bureau
After the tour, check out the Key West Aquarium. Built between 1932 and 1934, it’s one of Florida's oldest aquariums. While it may be small, the long building is lined with tanks that showcase the critters that populate the Florida Keys waters, like eels, lobster, seahorses and glowing jellyfish. You’ll also spot alligators, stingrays and rescued sea turtles in the larger tanks.
Next, get in some retail therapy at Kino Sandals, where you'll feel like you've been swept back in time to a sandal factory in Havana. Pick out a pair of handmade leather flip flops to take home.
Key West Aquarium — Photo courtesy of Nick Doll / Key West Food & Wine Festival
Ready for lunch? Continue the authentic Cuban experience at El Meson de Pepe, located in a historic red brick building off of Mallory Square. Try the Media Noche sandwich with sugar-glazed ham, roast pork, Swiss cheese, pickles and mustard dressing on sweet, pressed bread. Pair it with one of their signature mojitos.
Afterwards, take a leisurely stroll up Duval Street, and you’ll soon start seeing the funky art galleries and boutiques. Pop into Kermit’s Key Lime Shoppe at their new and second location at the corner of Duval and Petronia Streets. Enjoy a slice of their Key lime pie dipped in Belgian chocolate on a stick, and shop for Key lime gifts to take home.
Cut over to Whitehead Street and visit the Ernest Hemingway Home and Museum, where the infamous author lived and wrote during the 1930s. Entertaining tour guides will take you through the two-story house and recount the exploits and adventures of “Papa.” Over 50 polydactyl (six-toed) cats have the run of the property. Across the street, you can see the 1847 Key West Lighthouse.
Walk back to Duval to the Rum Bar at the Speakeasy Inn and have a from-scratch rumrunner with local mixologist Bahama Bob. Note the white gingerbread trim on the porch, which forms bottles and playing card symbols - their way of advertising as a speakeasy during Prohibition.
Fish at the Key West Aquarium — Photo courtesy of Nick Doll / Key West Food & Wine Festival
Grab a cab back down to Mallory Square, where the crowds will be gathering for Key West’s famed Sunset Celebration, a carnival-type event with jugglers, trained cats and fire-eaters.
If you’re not one for crowds and want a more upscale experience, then take Danger Charters' Wind and Wine Sunset Sail, where you’ll have a peaceful front-row seat to the sun’s departure, replete with world-class wines and hors d’oeuvres. If you’re like most people, you’ll already be planning your next visit, or, like some, contemplating never leaving at all.