Essential Key West: Best Things to Do in Key West

Key West is often described as quirky, eclectic, lush, colorful and sometimes downright odd. To capture the character of this southernmost place, pay a visit to several iconic spots. Be warned though – legend has it that many of the locals were once visitors who, once they felt the island’s languid tropical breezes and enjoyed its laidback vibe, decided to stay – permanently.

No trip here would be complete without paying a visit to the Ernest Hemingway Home & Museum, once the home of the island’s most legendary literary resident. Peek into his second-story writing studio and marvel at the manual Royal typewriter where he composed classics including “To Have and Have Not” and “For Whom the Bell Tolls.” The Spanish colonial villa with its lush surroundings and sprawling swimming pool is a registered National Historic Landmark. More than 40 six-toed cats (perhaps descendants of Hemingway’s cats) roam freely about the property, making this house and its gardens their home.

It’s no secret that Hemingway liked to drink, and during his Key West years (1931 to 1939), he was a regular at a watering hole – considered the original Sloppy Joe’s – that opened in 1851 on Greene Street. The bar was owned by his friend and fishing buddy Joe Russell; in 1937, Russell moved it across the street.

Today, it’s known as Captain Tony’s Saloon because it was bought in 1958 by the now-deceased boat captain and former Key West Mayor Tony Tarracino. Tarracino was a character known around the island as an avid storyteller; his memory and stories live on within the walls of his saloon. Soak up the history while enjoying a frosty one.

Don’t miss the current-day Sloppy Joe’s, on the corner of Greene and Duval streets. It’s a landmark open-air bar immediately recognizable thanks to its huge corner location, infectious live music pouring out and the annual Hemingway Look-Alike Contest held every July at the lively joint.

This photo op is a must: Just down the street from the Hemingway House is the Southernmost Point, a massive red, black and yellow concrete buoy erected in 1983 by the City of Key West to mark the southernmost point in the continental U.S. Today, it’s among the most-photographed landmarks on the island. Pose for a photo next to the iconic buoy that proudly stands just 90 miles from Cuba.

Hemingway would likely have felt right at home with the cast of characters that congregate nightly for the Sunset Celebration at Westin Pier and Mallory Square – like just about everything else on the island, it’s quirky and a bit offbeat.

The Key West homage to the end of the day features tightrope walkers, jugglers and animal acts performing alongside palm readers, artists and buskers. On the Westin Pier, there are a variety of performances and drink carts overflowing with the island’s finest tropical libations. Of the most seasoned performers, Dominique “The Cat Man” Lefort, draws huge crowds with his trained house cats that mimic circus tigers by jumping through fire hoops and performing other tricks. The Paris-trained Lefort, who studied drama, opera, mime and dance, incorporates his many talents into his bizarrely entertaining show.