1. POIPU BEACH-GRAND HYATT, Kauai. Even when the rest of the Garden Island is taking a rain bath, strollers can normally find sun on the arid south shore. Beginning with the Sheraton, a path swerves along low-key (by Hawaii standards) resorts. You can cut through the gardens for restaurants and shopping, or to take a gander at the weird Moir Gardens, a several-acre display of cacti. From Poipu Beach Park, a jogging path through condos and a greenspace ends at the Grand Hyatt Kauai, with Asian-inspired architecture and lush grounds that make it one of the world's premier destination resorts.
2. WAIKIKI BEACH, Oahu. Can't leave Waikiki off this list, although most of the hotels are glass towers. But you can drop in at the Royal Hawaiian, Moana Surfrider, and Halekulani for a touch of the golden years. The walk extends for a of couple miles to Kapiolani Park. Designer shops and gourmet eateries are sprinkled along Kalakaua Boulevard, the main drag.
3. WAILEA RESORTS WALK and KA'ANAPALI, Maui. Given that most of Maui's beaches are developed, it's not surprising that the Valley Isle has two great luxury beach strolls. The older development (1970s onward) to the north is Ka'anapali, where a Sheraton and Hilton bookend a mile-plus paved path. The Hilton's gardens are a respite, while some of the resorts (Maui Ocean Club) present a sea of flesh on lounges. Black Rock Beach at the Sheraton is where most of the action is (this place used to be called Dig Me Beach). A shopping center with multiple restaurants opens to the sand. Parking, at a series of lots, can be a hassle. Farther south in Kihei are the the Wailea Resorts, decidely more ritzy. The Grand Wailea is a worthy destination, with towering atriums and bloated Botero scultures. More than a half-dozen large public lots provide access to as many sandy coves.
4. MAUNA LANI-FAIRMONT and WAIKOLOA, Big Island. The South Kohala coast on the Big Island features a desert of black lava with a number of coastal oases, many featuring some of the best tropical resorts in the world. The walk from the Fairmont Orchid to the Mauna Lani doesn't offer much shopping, but rather striking coastal scenery along palms and coral-chunk beaches. The Mauna Lani Fishponds are a parkland unto themselves. Conversely, the Hilton in Waikoloa is like Disneyland, with a monorail, boat rides, a huge dolphin pool and man-made lagoon. Corinthian columns border a grand staircase that leads to the water. A path from the Hilton takes you along a wild coast with ponds (backed by new big bungalows) that eventually leads to the open sands of Anaeho'omalu Beach Park. The new Lava Lava Beach Club is an opportunity to sip rum drinks and munch pupus with your toes in the sand.
Trailblazer guides have more details on where to park to visit these resorts, as well as many others where you can enjoy the good life for free.