Surf capitals come and go, but for nearly half a century, one thing hasn't changed: The road to surfing stardom still rolls right through Haleiwa, gateway to Oahu's North Shore and some of the sport's most fabled waves: Pipeline, Sunset, Waimea. In a sense, Haleiwa, which marks one end of the "seven-mile miracle" stretch of beaches and some 40 surf breaks, is two different towns. One materializes every winter, when thousands of fans and photographers follow the planet's best surfers—including North Shore residents Jamie O'Brien, Pancho Sullivan, and Fred Patacchia—as they converge for high-profile contests like the World Cup and the Pipe Masters, braving sometimes-lethal shallow reefs, monster tubes, and wave faces that can top 30 feet. Once the mobs and the hype (and the swells) die down, the other Haleiwa reappears: a sleepy old sugar-mill town where Jack Johnson learned to strum a guitar at backyard barbecues. It's a laid-back anti-Waikiki, where feral chickens shriek from the branches of mango trees, locals gear up at any of a dozen or so surf shops and refuel on ahi tacos at Cholo's, and grandparents cheer on longboarding preteens in the annual Menehune Surf Championships. On the job front, survival often entails doubling up on tourist-related gigs, driving an hour or so to Honolulu, or sponging off your friends. On the surfing front, respect is earned, not granted: Wise newcomers start out at the less hyped, less crowded breaks, such as Kammies or the more challenging Pupukea, until they find their place in the pecking order.
The good news about real estate on the North Shore: Prices are leveling off. The bad news: The median home price is around $900,000, and even that won't get you oceanfront. Plan B? Pony up $1,500 to rent a modest one-bedroom until the rep from Quiksilver calls.
Ventura, California. Close to Rincon, one of California's best point breaks, along with stellar surfing at Emma Wood and Silver Strand—and just far enough from Los Angeles. Ventura hosted the first prize-money surfing contest (in 1965), and it was here that three-time world champ Tom Curren and the surfing/filmmaking Malloy brothers perfected their moves. Ventura's cool old downtown—wedged up against the foothills a few blocks from the Pacific—is packed with eateries, thrift shops, and bookstores.