Pop. 6,323
GPS: 24° 55'N 80° 38'W

Strung across six islands in the lower Florida Keys, the village of Islamorada is set between a Gulf Stream—warmed Atlantic Ocean—home to sailfish, wahoo, dolphin, tuna, sharks, and North America's only living coral reef—and the Florida Bay, rife with bonefish, snook, and snapper.

There's so much wildlife here, it really feels like the sportfishing capital of the world," says captain Eric Bass (yep, his real name). But while Bass's boat is one of a hundred-plus angling for tourists, competition gives way to camaraderie in the tight-knit community. Back on dry land, neighbors congregate at 40-acre Founders Park, a former resort that now hosts kayak socials and float-in movies (kayaks starting at $15 per hour ; foundersparkwatersports.com). The latest object of locals' devotion is kiteboarding, made friendlier by offshore sandbars, grass flats, and 15- to 25-knot winds (sevensports.com).

Bentley's, a raw bar and restaurant at mile marker 82.8 on Route 1, will cook your catch and serves homemade conch fritters and escargot Capriccio (keysdining.com/bentleys).

Get free use of bicycles and private, oceanfront views at the Pines and Palms Resort (doubles from $89; pinesandpalms.com).