Puerto Rico
A MULTISPORT DRAW, Puerto Rico offers enough mountain biking, hiking, snorkeling, and diving to keep an energetic visitor occupied for months. But it's the surfing—centered around the town of Rincón, on the western shore— that you'll come back for. Tied with Huntington Beach, California, for hosting the most ISA surfing events, Puerto Rico reigns as the surf mecca of the Caribbean, with 310 miles of coastline. "All the other islands have open windows, but they're small," says Rip Curl team rider and Puerto Rico native Brian Toth. "PR has huge open windows for swells to come through." The 2007 World Masters had surfers barreling off Rincón's point break, Maria's, which produces waves up to 14 feet. Toth's favorite break? Jobos, near the town of Isabela, 45 minutes from Rincón, which pumps perfect rights most days.

PLAYTIME: Waves break consistently from October through April—pass up the standard foam board for a lesson on a classic fiberglass longboard with Playa Brava Surf Underground. Surf-school owner Tupi Cabrera takes pride in his island because it has the widest variety of waves and, in his words, "it's freakin' cool!" Ninety-minute lessons from $40; playabravasurf.com

ISLAND LIVING: Rincón's luxurious Horned Dorset Primavera Hotel has 22 private, plunge-pool-adorned villas on four hillside oceanfront acres. Doubles from $610; horneddorset.com