Key West

Key West is the far frontier, edgier and more eccentric than the other Keys, and also far more captivating. At its heart, this 7-sq-mile island feels like a beautiful tropical oasis, where the moonflowers bloom at night and the classical Caribbean homes are so sad and romantic it’s hard not to sigh at them.

While Key West has obvious allure, it's not without its contradictions. On one side of the road, there are literary festivals, Caribbean villas, tropical dining rooms and expensive art galleries. On the other, an S&M fetishist parade, frat boys passing out on the sidewalk and grizzly bars filled with bearded burnouts. With all that in mind, it's easy to find your groove in this setting, no matter where your interests lie.

As in other parts of the Keys, nature plays a starring role here, with some breathtaking sunsets – cause for nightly celebration down on Mallory Sq.

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What to pack for Key West, Florida