Key West is more than just funky sunset parties, late night bars, and pristine beaches, it has a long history and a vibrant cultural scene that most tourists never learn about or experience. It was originally inhabited by the Calusa (kah LOOS ah) Indians, also known as the “Shell Indians,” “discovered” by Juan Ponce de Leon, the Spanish explorer, in 1521. Except for the Calusa Indians, Key West was uninhabited until 1822 when Navy Lt. Commandant Matthew C. Perry planted the U.S. flag on the island and claimed it for the United States. For decades it has been a haven for writers, artists, and other creative types like Ernest Hemingway, Judy Blume, Tennessee Williams, Jimmy Buffet, and Calvin Klein, looking to get away from at all.
What to Do
The best way to experience Key West like a native is to slow down the pace and walk to Smathers and Higgs Beaches to watch the sunrise. Or maybe explore the quiet streets in hidden neighborhoods, visit the streets of the historic district in Old Town, and hang out at the Green Parrot Bar whose slogan is “A sunny place for shady people.” For most people, the allure of the crystal clear water is too hard to resist so if you are into water sports, take your morning stroll to Higgs Beach and take a swim off the pier or sign up for water activities like snorkeling and parasailing.
Nature lovers won’t want to miss the Key West Butterfly and Nature Conservancy for a chance to walk among hundreds of butterflies and birds.
Relax at night and take in a live theater performance at the Red Barn Theater. Built in 1829, it was once a carriage house but has staged works by prominent writers and playwrights such as , the former U.S. Poet Laureate.
Don’t Miss: Fantasy Fest, an outrageous, even for Key West Halloween party that’s akin to Mardi Gras excess.
Where to Eat
Be sure to head to historic Bahama Village for brunch at Blue Heaven, it’s an authentic Conch experience where blueberry pancakes and mile high Key lime pie vie for celebrity status. Hippy dippy and off-beat, brunch is served al fresco beneath towering trees while at your feet cats, hens, and roosters share patio space and keep guests company.