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Dear Trip Coach...
I retired about two years ago, and my partner, Ann, just earned an advanced postgraduate degree. We're celebrating our milestones with a trip to Oahu. We only have five days, so we need to maximize our time, but we also want to build in a little downtime to relax and reflect. Betsy Cheney, Rumney, N.H.
"We're staying in Waikiki for the first three days. Should we spend the last two on another island?" Switching islands would be ambitious for a five-day trip. Plus, visiting Oahu and seeing only Waikiki is sort of like visiting the U.S. and seeing only New York City. Instead, spend your last two days on Oahu's North Shore.
"Do we need to rent a car?" Not in Waikiki: Driving is hectic, parking is expensive, and you can walk everywhere. Taxis are plentiful if you want to leave the neighborhood. At the airport, grab the Roberts Hawaii shuttle (866/898-2519, robertshawaii.com, $9, every 20 minutes). When you're ready to go to the North Shore, rent a car in Waikiki.
"We have friends who got engaged on Diamond Head--we'd love to see it." Diamond Head looks like an easy walk from Waikiki, but the trail entrance is farther than it seems, so hop in a taxi. The 0.8-mile trek up the crater involves climbing 279 steps; bring water and pace yourself. From the top, you can see Oahu's south shore and, on a clear day, the island of Molokai. Start early! By 10 a.m., tour buses roll in and the sun heats up (6 a.m. to 6 p.m., $1 to walk in, $5 per car).
"Scenic, swimmable beaches are a passion of mine." When most people think of Waikiki, they think of Kuhio Beach: It has surfboard-rental stands, outrigger-canoe tours, and a big statue of surfer Duke Kahanamoku. Don't let the crowds deter you--people-watching is part of the fun. A half-mile east is Kaimana Beach, which attracts more locals--kayakers, triathletes in training, and families playing in the shore break.
"Where can we buy gifts made by local craftspeople?" Take a taxi to Native Books/Na Mea Hawai'i (1050 Ala Moana Blvd., 800/887-7751, nativebookshawaii.com). The shop carries books about Hawaiian culture, and jewelry, crafts, and spa products. It also brings in craftspeople and kupuna (elders) to give demos of Hawaiian practices like hula dancing. Native Books is a partner in Mana Hawai'i, a store in the new Waikiki Beach Walk complex. Stop in for gifts, ukulele lessons, or a Hawaiian-language class (808/923-2220, 226 Lewers St., activities are free).
"Both of our fathers were Navy men, so we want to visit Pearl Harbor." If you have time to see only one part of Pearl Harbor, make it the USS Arizona. The memorial sits over the eerily visible remains of the battleship, which sank when it was bombed in 1941 (808/422-2771, nps.gov/usar, free). The tour of the Battleship Missouri Memorial, where the Japanese officially surrendered, is also memorable (877/644-4896, ussmissouri.org, $16). Military buffs particularly enjoy the USS Bowfin Submarine Museum & Park (808/423-1341, bowfin.org, $10) and the Pacific Aviation Museum (808/441-1000, pacificaviationmuseum.org, $14). Pearl Harbor is 10 miles from Waikiki. V.I.P. Trans runs shuttles every 45 minutes (viptrans.com, round trip $9).
"Is there anything else we should do while we're in Waikiki?" For an unforgettable evening, sit under the big kiawe tree on the terrace at House Without a Key, the casual restaurant at the luxurious Halekulani hotel. Order a Halekulani Sunset cocktail and listen to musicians play Hawaiian tunes as the sun sets (2199 Kalia Rd., 800/367-2343, halekulani.com, performances from 5 p.m. to 8:30 p.m.).
"Where can we get Hawaiian food?" For Hawaiian dishes like laulau (pork wrapped in taro leaves and steamed), and lomilomi salmon (a salad of cured salmon, tomato, and onion), go to Ono Hawaiian Food, on Waikiki's outskirts (808/737-2275, 726 Kapahulu Ave., $11). You'll also come across poi, mashed and strained taro root, at various spots; it's a decidedly acquired taste. "Local food," meanwhile, includes elements of Hawaiian food, but it also has influences from Japanese, Filipino, Korean, Chinese, and mainland American cuisines. A "plate lunch" includes a meat such as beef teriyaki or chicken katsu (fried chicken), two scoops of rice, and a scoop of macaroni salad. Police and surfers line up at Rainbow Drive-In for barbecued pork sandwiches or hamburger steak (3308 Kanaina Ave., 808/737-0177, from $3).
"We want to have one special dinner." In the early 1990s, a dozen Hawaii-based chefs pioneered Hawaii Regional Cuisine, a movement emphasizing fresh, local ingredients. Roy Yamaguchi, a founder of the movement, isn't exactly a secret--he has 34 restaurants in the U.S. and Japan--but he remains an island favorite. Roy's at Waikiki Beach Walk is the latest outpost of his empire (226 Lewers St., 808/923-7697, roysrestaurant.com, entrées from $21). Fusion fans adore Hiroshi Eurasion Tapas. Chef Hiroshi Fukui brings an Eastern touch to local fare (500 Ala Moana Blvd., 808/533-4476, hiroshihawaii.com, tapas from $7).
"We love cultural history, and Ann is interested in religious history. Do you have any recommendations for us?" Bishop Museum, seven miles from Waikiki, showcases Polynesian history (1525 Bernice St., 808/847-3511, bishopmuseum.org, $16). Stop on your way to the North Shore. As for religious history, ancient Hawaiians constructed heiau, temples made of lava stones. Some still exist, in varying states of ruin. Oahu's largest, Pu'u O Mahuka Heiau, overlooks Waimea Bay, on the North Shore. From Kamehameha Highway, turn onto Pupukea Road, drive three quarters of a mile, and look for the sign.
"What else is there to do on the North Shore? And where should we stay?" The point of the North Shore is that there isn't much to do but relax. It's small-town Oahu the way it used to be. The main town, Haleiwa, is mostly shrimp trucks (just what they sound like), surf shops, and shave-ice stands. (Aoki's Shave Ice, at 66-117 Kamehameha Highway, is better than the rest, without the lines.) In winter, people come from all over to watch surfers on the monster waves at Banzai Pipeline, Waimea Bay, and Sunset Beach. In summer, the calmer waters attract swimmers and snorkelers. Ke Iki Beach Bungalows rents cottages with kitchens (keikibeach.com, from $135).
"I'm 60, but I'm thinking about taking a surfing lesson." Go for it! The waves at Waikiki Beach are small and gentle--perfect for beginners--but they're also crowded all the time. You're better off learning on the North Shore. Surf N Sea, a shop in Haleiwa, offers lessons for all levels (800/899-7873, surfnsea.com, two-hour lessons from $85).