Shipman House, Hilo
Number of accommodations: 5
When Jack London stayed here, in 1907, things looked much as they do now: wicker rockers on a wraparound porch, a grand staircase made of wide-plank fir polished to a shine, a claw-foot tub poised on black-and-white tiles. The house, a turreted buttercream-colored confection a few blocks from downtown Hilo, has been in the same family for more than a century. But it wasn't until 1994 that Barbara Ann Andersen, a great-granddaughter of the owners who hosted London at what was then their private residence, took possession of the place and, three years later, reopened it as a hotel. Stately, immaculate, and filled with so many well-preserved antiques that guests are given a five-page catalog for a self-guided walking tour, the main house has a library, a solarium, and three guest rooms. A separate building, built in 1910, is divvied up into two guest quarters, both with window seats and spare, tasteful furnishings. For fun, stroll the nearby seafront, small history museums, and bevy of knockout botanical gardens. Hilo may not be as sophisticated as you'd expect from the second-largest city in the state, but that's precisely its appeal (808-934-8002; www.shipmanhouse.com; doubles, $179-$209; housekeeping; value; view).

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KAUAI
The southern coast hosts near-constant sun, old sugar towns, and the golden strands of resort-packed Poipu; cruise inland and you'll end up staring into the giant mouth of Waimea Canyon. The coastal highway peters out near the north shore, arguably the island's most enchanting corner, with deep-green valleys, secluded beaches, tony towns, and the legendary Na Pali cliffs, rising 4,000 feet above the sea.

Secret Beach Hideaway, Kilauea
Number of accommodations: 3
Secret Beach is no secret—but it sure feels like one. A mile-long strand on the lush north shore of Kauai, it is reachable in either of two ways: by driving along a dirt road, parking in a small lot, and scrambling down a steep, often slippery footpath next to a barbed-wire fence—or by emerging from your very own hilltop mini-mansion, strolling across your private patio, and zigzagging through an obsessively tended tropical garden that slopes down to the sand. The Secret Beach Hideaway consists of three one-bedroom cottages set well apart from each other on 11 acres and surrounded by another 60 acres of state-protected ironwood trees, ravines, and waterfalls. The setting alone is worth a king's ransom—the superluxe cottages seem almost beside the point. Owner and decorator Michele Hughes made each unique and stocked them all with high-end goodies: sheets with 400-plus thread counts, Sub-Zero refrigerators, All-Clad cookware. You're on your own for housekeeping and meals, although catering (and a massage therapist) can be arranged. Alternatively, Kilauea, with its smattering of restaurants and clutch of charming country churches, is five minutes away by car. Many more choices await at Hanalei, a scant 20-minute drive (provided you don't become preoccupied with the terraced taro fields and waterfalls en route). There, you'll find loads of restaurants and shops, as well as catamaran operators who will take you along the spectacular Na Pali coast (800-820-2862; www.secretbeachkauai.com; cottages, $395-$425, with a three-night minimum; beach; nature; view).