Florida’s most beloved and quirky island.
Key West’s Beachy Paradise
Credit: Ian Dagnall / Alamy

The no-nonsense Conch Republic of Key West is still affordable after two decades of development. Once an artists’ enclave, the island still channels a funky spirit, with laid-back restaurants and bars and quirky bed-and-breakfasts. When you’re not exploring by bicycle, spend time on the beach, breaking only to sip a chilly concoction.

Green Parrot

A jazzy live band accompanies the rough-looking bartenders, who serve $3 brews to a wide range of characters beneath twinkling green lights.

The Mermaid & the Alligator

With at least 80 inns and B&B's squeezed onto the eight-square-mile island, Key West may well be America's most "inn" town. So what makes the Mermaid & the Alligator stand out? Try the crystal chandelier glittering from the royal poinciana tree out back, or the plunge pool with built-in bench for sipping Meursault. Or is it simply that the inn, though only a 10-minute walk from the beach, hides in a palm and bromeliad jungle, secure from tourist-mobbed Duval Street? The owners intended to create a respite from Key West's hubbub when they bought the 1904 Victorian house five years ago. They planted every exotic they could find, then decorated the rooms with refreshing details like Polynesian tapa cloths and Haitian and Cuban artwork depicting island life. None of the nine guest rooms have phones or TV's, but instead encourage lingering at mahogany writer's desks. But first, you'll need to check in at the kitchen—there's no reception desk here.

Fort Zachary Taylor

Spend the day at the 1850s park (don’t miss the fascinating antique desalination plant). Here, you’ll also find one of the few beaches in Key West with showers and picnic tables. Tip: bring waterproof sandals—the beach is pebbly.

B.O.'s Fish Wagon

The funky shackgets its charm from a mishmash of ripped fishing nets, no sniveling signs, and a rusted truck. And yes, the fritters are superb.

Sloppy Joe's

In Old Town, nurse a $7 frozen Rum Runner as the live music plays throughout the day.