Key West Connection
Close the guidebooks and let a local lead the way.
By Cricket Desmarais
What’s not to love about an island city known for its fabulous sunsets, tropical breezes, and two oceans divided by a street just over a mile wide? Key West is a mecca for artists, dreamers, and those with salt in their blood. Closer to Cuba than the nearest Walmart, Key West is a world away from a world, where people proudly tout bumper stickers on colorfully painted cars that say, “Slow down—This ain’t the mainland!”
I left the bustle of New York City nearly 20 years ago and never looked back, trading my corporate job and the subway for a rusty bike and a pair of flip flops to discover a culture like I’ve never known before. From life on land to saltwater adventures, there’s never a dull moment. The trick is to know where to find it.
Sure, the world-famous Duval Street is intriguing, with its gamut of Old Town bungalows, Victorian mansions, historic landmark buildings, high-end boutiques, art galleries, and inns on the Atlantic end — to boozy bars, bustling restaurants, and T-shirt shops leading up to the Gulf of Mexico — to theaters, museums, hotels, churches, and cabaret drag shows in between.
But don’t forget to step off the beaten path and traverse the 16 streets that cross Duval. Round the bend to find a treasure trove of bistros, bars, and boutiques, each with its own special taste of Key West. You’ll also find colorful bursts of jasmine, frangipani, bougainvillea, and orchids and a huge variety of palms that frame a mishmash of the island’s Old Town architectural styles like cigar-maker cottages or classic Victorians with widow’s walks, sprawling verandas, and gingerbread accents.
If It’s Free, It’s For Me
There are five free small public beaches: Higgs, Smathers, Dog Beach, Rest Beach, and South Beach. But because the Florida Keys and Key West boast the world’s third largest living coral barrier reef, which prevents the formation of natural stretches of sandy beach, most of the natural shoreline is dotted with coral rocks and mangroves, with sand imported from the Bahamas (if there is any sand at all). So don’t be disappointed when you get there.
You can also head to the free-entry Florida Keys Eco-Discovery Center, which provides a look into the ecosystems of the Florida Keys. Located at the south end of the island near Fort Zachary Taylor Historic State Park, the center features more than 6,000 square feet of interactive exhibits that interpret the ecology of Keys’ habitats, a 2,500 gallon living reef exhibit, and a theater with a short film that’ll awe and inspire you with its natural and underwater filmmaking by renowned marine cinematographer Bob Talbot.
How Not to Look Like a Tourist
The biggest way to look like a tourist is to forget that the motto here is “One Human Family,” the island’s much-embraced proclamation of human equality. What might look out of place to you in your own hometown — drag queens in glittering gowns belting out show tunes, intoxicated street “vendors” selling hats and roses made from palm fronds, and same-sex couples walking down the street holding hands — is just another day in the paradise that 25,000 locals call home. Unless you’re….
Photo: Blue Heaven