And Don't Miss: Sunset cocktails at the Montauket Hotel. People lie out on the lawn overlooking the bay and cheer as the sun goes down (88 Firestone Rd.; 631-668-5992).
–Ondine Cohane

North Shore, Hawaii

Why: The surfers and hippies who have taken charge of this swath of coast on Oahu's north side have fought off the concrete high-rises and designer outposts that characterize Honolulu. Instead, you'll find sleepy towns, horse ranches, pineapple plantations—and of course miles of the long, rolling waves that make it one of the world's best surf spots. The state of Hawaii and the North Shore Community Land Trust, a collective whose members include pro surfer Kelly Slater, have already preserved a thousand acres of land—among the real estate a section overlooking the Banzai pipeline—to keep it relatively undeveloped. Come summer, most of the tourists have departed and gentler breaks arrive.

How to Get There: Most major carriers fly to Oahu from hubs like LAX and San Francisco (a 5.5-hour flight), and Seattle and Las Vegas (6 hours), for about $500 in summer. Rent a car at the airport; it's about a 45-minute drive to the North Shore.

What You'll Need: In summer, temperatures average 85 degrees but often top 90, so pack plenty of sunblock. Newbies will want a rash guard to protect their upper body from the strong sun and the nasty skin irritations that come after a couple of hours on a board. If you bring your own surfboard, be sure to have a sturdy cover to protect it from damage during the flight. Or you can rent one from Surf-N-Sea—it also offers surf lessons and PADI certification (62-595 Kamehameha Hwy.; 808-637-9887). Casual clothes and flip-flops are de rigueur in this crowd. In fact, if you dress up, you'll be considered even more of a haole (the sometimes disparaging term for Caucasians, particularly tourists).

Where to Stay: On the beach right off Kamehameha Highway, Ke Iki Beach Bungalows is the most popular option for hard-core surf enthusiasts who want the quickest wave access, so be sure to book early. Choose one of the ocean-view bungalows; the Orchid has the best vista of all. But be warned: There is no daily maid service (808-638-8229; keikibeach.com; doubles, $135–$230). Turtle Bay, the only real resort in this area, is considerably fancier, with golf courses and tennis courts, but it's away from the action you'll find later at Sunset Beach. And although there is a surf break, most days it's too heavy for beginners (808-293-6000; turtlebayresort.com; doubles, $289–$482).

What to Do: On your first day, start off by refreshing your board skills. Hans Hedemann is one of the best surf schools on the island, and if you're staying at Turtle Bay there's a location right downstairs. As with most surf-related businesses, the front office is often disorganized—be sure to confirm your lesson—but the teachers are excellent. Ask for Bobby, a Vermont transplant who is knowledgeable and calm. Lessons are scheduled for 9 A.M., noon, and 3 P.M.—the middle of the day means harsh sun but emptier waters (808-924-7778; hhsurf.com; lessons, $75–$150).