Your base for the next four days is the historic Halekulani, a refined oasis in rollicking Waikiki (808-923-2311; halekulani.com; doubles, $660–$730 for a recommended room). The first course of action is to unknot from the flight, so after unpacking, head to the Halekulani's splendid spa for a massage (Chaitman will have made the appointment for four hours after your flight arrival). Feeling too restless? Take a dip in the ocean instead. The beach, just across the pool deck, is a small sliver of the crescent that fronts Waikiki's biggest hotels, so expect to share the waves with the hoi polloi. Still, one look at the celadon waters unfurling onto the sugary sand and you'll understand Waikiki's unflagging popularity. The sun sets around 7 p.m. in May, so by 6:30 you should be seated at the hotel's seaside lounge, House Without a Key, where purple orchids adorn the mai tais and a nightly trio plays South Pacific ballads from the 1940s and '50s. Stay until the sky darkens and a spotlight illuminates the small stage and the backdrop of crashing waves. Tomorrow will be a long day, so stay close to home for dinner. Luckily, Nobu, one of the few sushi chains worth the hype, recently opened across the street at the Waikiki Parc hotel. The fish couldn't be more artfully presented, and the service is aces, but be warned: The dining room is nightclub noisy (2233 Helumoa Rd.; 808-237-6999; entrées, $12–$48). For a quiet end to the evening, stroll the moonlit beach to Kuhio Beach Park and pay homage to Duke Ka-hanamoku, father of modern surfing. You'll need him on your side for your surf lesson on day 5. Back at the Halekulani, if you haven't yet succumbed to jet lag, duck into the hotel's seductive Lewer's Lounge for a nightcap.

Day 2: Honolulu

Before turning in last night, you ordered room service breakfast to be delivered by 6 a.m. The time change is in your favor, and besides, all will be forgiven when you're dining on your oceanfront patio (Kona coffee in hand), watching the sun rise over the day's first destination, Diamond Head Crater. The hulking, blistered hollow that punctuates the southern end of the Waikiki strand is the first of several volcanoes you'll be scrambling up in the next two weeks. It's among the smallest—just 760 feet above sea level—and the relatively short walk (0.8 mile) up a mostly paved trail has a big payoff: a glorious panoramic view. Arrive at the park entrance at 7:30 a.m. to beat the crowds and the heat on the mostly shadeless climb. By 8:30 you'll be at the summit, ogling the sparkling coastline and the green hills and valleys that cloak south Oahu to the enviable mansions of the Kahala neighborhood. The viewing platform you're standing on served as a command post during World War II (you'll have seen gun emplacements on your way up).

Be back in the parking lot by 9:30 a.m., where you'll meet your guide, Nanette Napoleon (a descendant of the Bonapartes, by way of Tahiti). For the next four hours, Napoleon, a Hawaiian historian, will lead you to sights in Windward Oahu rarely seen by travelers, including the ruins of Ulupo Heiau, a once prodigious tenth-century temple set within a recently restored garden and He'eia State Park (46-465 Kamehameha Hwy.; 808-247-3156; friendsofheeia.com), overlooking a glassy bay and a 600-year-old fishpond. She'll also take you to Nu'uanu Pali Lookout, well-trod tour bus territory but still worth visiting, as much for the stunning view as for the site's somber significance. It was here that Kamehameha the Great, the first king to reign over all the Hawaiian Islands, conquered Oahu in 1794, launching a 100-year dynasty that ended only when the islands became a U.S. territory. Born on the Big Island around 1758 (some 20 years after George Washington), Kamehameha was prophesied to be a "killer of chiefs," and after a childhood spent in hiding, he became just that. The Big Island fell first, then Maui and Molokai; in Oahu, the formidable warrior (he stood 61/2 feet tall and weighed some 300 pounds) led his army through Nu'uanu Valley, driving the defending forces onto—and then over—the valley rim's steep cliffs. Thousands died, many at the hands of Kamehameha's female soldiers, and their remains still lie buried beneath those wind-ravaged cliffs. Disinclined to meet the same fate, the chief of Kauai and Ni'ihau ultimately capitulated, and Kamehameha built his royal court on the shores of Waikiki.