At the southernmost point of the continental United States, Key West feels like its own world — a sun-drenched island with a soul as colorful as its pastel-hued homes. This quirky, creative community has long drawn dreamers, artists, writers, and wanderers who find inspiration in its laid-back lifestyle and inclusive spirit. History, culture, and fun collide here, from Ernest Hemingway’s former home to the clucking chickens and roaming cats of historic Old Town. Visitors can toast sunsets at Mallory Square while street performers celebrate another perfect day, explore conch-style architecture, or savor Cuban- and Bahamian-influenced cuisine. The town’s festivals, from literary tributes to wild Fantasy Fest parades, capture the playful, imaginative heart of the island. Duval Street is the island’s pulse, transitioning from morning coffee at Cuban cafés to jazz-filled evenings in open-air bars. Boutiques, galleries, and culinary experiences abound, including sunset cocktails at La Concha’s Tropicado Mojito Bar and hands-on cooking demos at the Key West Cooking School. Outdoor adventures stretch from snorkeling the living coral barrier reef to kayaking mangrove tunnels or cycling the scenic Overseas Heritage Trail. Key West’s locally owned shops, historic hotels, and vibrant events, paired with a deep commitment to inclusivity and culture, make the island a one-of-a-kind coastal escape. #americasfavoritesmalltowns
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Key West
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