By Kerry Mastrobuoni
Some destinations impress us with their beauty; others win us over with their food, culture, and people. For me, Key West checks all those boxes.
I keep returning, drawn by the turquoise water, colorful characters, and carefree spirit that seems to exist nowhere else quite like it. Key West isn’t just a destination. It’s a feeling.
Getting there is part of the adventure. You can fly directly into Key West International Airport, but I recommend making the drive from Miami at least once. The Overseas Highway carries you across a string of islands, with spectacular blue water stretching in every direction. Along the way, we stumbled upon Robert Is Here in Homestead, a legendary fruit stand that began in 1959 when a six-year-old boy named Robert sold cucumbers beside the road. Today, it’s famous for exotic fruits, local honey, tropical milkshakes, a petting zoo, and live music.
Further along, stop at Robbie’s Marina in Islamorada to feed the enormous tarpon gathered beneath the dock. It’s unforgettable entertainment, but watch those fingers! We learned that lesson the hard way.
Arriving in Key West feels like entering another world. This tiny island, just four miles long and one mile wide, is actually closer to Cuba than Miami. Its history was shaped by shipwreck salvagers, Cuban cigar makers, fishermen, and free spirits. It also became a haven for writers. Ernest Hemingway found inspiration here in the 1930s, and you can tour his former home, now famous for its colony of six-toed cats. Playwright Tennessee Williams made the island his longtime home, while one of my favorite poets, Robert Frost, also spent time here in the winter months. Perhaps they were all drawn to the tropical light and warm sanctuary that make Key West so unforgettable.
As you wander the narrow streets, admire the pastel-colored conch houses, lush gardens, and inviting porches. And watch where you walk! Roosters roam freely, strutting through traffic as if they own the place. In Key West, apparently, they have the right of way!
Great food is another part of the island’s personality. Latitudes on Sunset Key offers spectacular waterfront views and an elegant atmosphere. Louie’s Backyard is another favorite of mine, serving oceanfront dining with Caribbean-inspired flavors. Hot Tin Roof offers sophisticated cuisine overlooking the historic harbor. For something more casual, seek out neighborhood bars where conversation flows as freely as the drinks.
After dinner, the energy ramps up along famous Duval Street. We always stop at Irish Kevin’s, where live music, hilarious performers, and audience participation make it impossible not to join the fun. This little island certainly knows how to entertain you!
No visit is complete without the Sunset Celebration at Mallory Square, where artists, musicians, and street performers gather each evening to watch the sun sink into the Gulf.
Don’t spend your entire visit on land. Getting out on the water is a must! Explore the backcountry by boat, cruise past mangrove islands, or anchor at a beautiful sandbar. There’s nothing like stepping into crystal-clear shallows, swimming in the warm water, and soaking up the sunshine surrounded by all the natural beauty.
Key West is history, humor, incredible food, and wonderful people wrapped in tropical sunshine. What more could you ask for?
Somehow, no matter how many times I visit, my compass always points me back to Key West.
I’d love to hear from you! Share your
travel tips and ideas at Kerryscompass@longislandmediagroup.com. Always let your compass lead you somewhere worth remembering.
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