There’s a saying in Florida: the further north you go, the more southern you get.

Nowhere is this more true than Key West – the southernmost point in the continental United States – which serves up an oh-so-interesting blend of Cuban, Southern and uniquely Floridian culture. It’s a place where anyone – from beach bums to party animals to history buffs – can find plenty to keep them occupied.

Above all, Key West is known for its counter-culture. A flamboyant collection of fire jugglers, stilt walkers and musicians appear each sunset along Mallory Square, while “clothing optional” bars serve strong drinks along Duval Street (see a full list of bars in Key West here).

Families and historians alike will appreciate the Mel Fisher Maritime Museum and the Ernest Hemingway Home (open year round; admission includes 30 minute guided tour).

And let’s not forget desert: Key Lime pie, a sweet and tangy pie made from local limes, is not to be missed.

Sure, Key West is the biggest draw for most visitors, but the more northern keys (meaning “small islands”) are worth exploring, too. Below packs in the best the keys have to offer in five days…Continue