Day 4: Old Honolulu

This morning's breakfast won't be the healthiest, but it may be the most memorable. Leonard's Bakery, just outside Waikiki, is the place for malasadas—Portuguese doughnuts stuffed with cream (pineapple, coconut) or dusted with sugar (933 Kapahulu Ave.; 808-737-5591). Grab a few to go (make sure they're hot) and drive over to the Honolulu Academy of Arts by 10 a.m. (900 S. Beretania; 808-532-8700; honoluluacademy.org). You could easily spend half a day touring this museum's wide-ranging collection, but today you'll have just an hour before setting out for Shangri La, the private estate of Doris Duke, now a museum administered by the Honolulu Academy. So use your time wisely: Skip the Islamic room (you'll be getting an eyeful soon enough), but try not to miss the gilded Buddhas in the Bhutan exhibit (up until May 23) or the vibranatly colored paintings and artifacts in the Hawaiian Arts section. At 11 a.m., you'll meet the Shangri La tour in the courtyard and soon after, you'll be piling into a van and on your way to the rarefied Black Point neighborhood. Notoriously private, Duke built her oceanfront sanctuary, hidden from view behind a lava rock wall, in 1937, covering every square inch with pieces from her vast Islamic and South Asian art collection. The architecture, gardens, and furnishings all adhere to the motif, from the inner courtyard paneled with Turkish tiles to the master bedroom's white marble walls inlaid with semi-precious stones. Snap photos on the lanai overlooking Duke's favorite surf break, and consider the youthful passion that led to all this painstaking beauty—Duke was just 25 when she began building her Shangri La (4055 Papu Circle; 808-532-3853; shangrilahawaii.org).

Back at the Honolulu Academy by 2 p.m., pop into the terrific gift shop for a few souvenirs, then dash over to Chinatown for a late lunch at Little Village Noodle Shop. You'll be having a big dinner, so try to make do with dumplings, a citrusy pecan salad, and slices of spicy black pepper beef (1113 Smith St.; 808-545- 3008; entrées, $9–$20). After lunch, stroll the galleries of Chinatown; pick up a walking map at Mark's Garage, an alternative art space at 1159 Nu'uanu Avenue. Smart boutiques and cafés, along with more galleries, are moving into the thirties-era buildings, but you'll still find plenty of the neighborhood's old character in the crack-seed stores, acupuncture clinics, and fish markets. Before you leave, check out the lei shops on Maunakea Street and the throng of pan-Asian food stalls at Maunakea Marketplace (1120 Maunakea St.).

Work off lunch at the hotel pool or the beach. Tonight is your last night on Oahu, so plan to live it up—starting with dinner at 8 p.m. at the island's top restaurant, Alan Wong's (1857 S. King St.; 808-949-2526; entrées, $28–$52). A champion of Hawaiian ingredients, Wong started a movement that's now spreading to the rest of the islands. Feeling gluttonous? Order one of the five- or seven-course menus. Otherwise, start with an appetizer (roasted duck nachos, perhaps), follow with an entrée (maybe Kona coffee–crusted strip steak), and by all means, spring for the dessert sampler (usually featuring Waialua chocolate from the North Shore). After dinner, head back to Chinatown (it's a five-minute drive from here) for great jazz clubs—including the Green Room at Indigo, a Balinese boîte (1121 Nu'uanu Ave.; 808-521-2900).