HANA HIGHWAY More of a journey than a place, Highway 360, colloquially known as the Hana Highway, is perhaps the loveliest and most diverse 50 miles in all of Hawaii. Sights include but are
not limited to, dozens of cascading waterfalls, one-lane bridges arcing across cliffsides wrapped in hanging gardens and charming small towns.
KAANAPALI Kaanapali experienced a surge of popularity in the ‘60s as developers built resorts here to rival the beaches of Waikiki on Oahu — and they succeeded. It’s easy to see why this former sugar plantation was chosen as the island’s first planned resort destination: the beaches.
KAHULUI Kahului is Maui’s busiest port and most populous metro area. This workaday town of some 20,000 people is usually the first city visitors to Maui see after touching down at the nearby Kahului Airport.
KIHEI This unpretentious South Maui town draws locals and visitors to its beaches.
LAHAINA The most frequently visited spot on the island, Lahaina is the only town in leeward Maui with a genuine downtown. Its primary draw is Front Street, a crowded main drag where a variety of restaurants, shops and hideaway cafes tucked into side streets create a maze of quirky charm.
PAIA Once an plantation town centered on Hawaiian Commercial & Sugar Company, today Paia enjoys its status as one of the top windsurfing destinations in the world. At nearby Hookipa Beach Park — host of the annual Aloha Classic Wave Championships, the crown jewel of wave sailing events — sailboarders perform complex aerial maneuvers.
UPCOUNTRY With its mild climate, fertile soil, grazing lands and diverse botanicals, Upcountry has become the Maui version of Napa. Upcountry is where boutique food emporiums and the island’s forward-thinking chefs get top-quality organic ingredients. Upcountry constitutes the landscape surrounding Haleakala from the 3,000-foot elevation all the way up to the volcano’s cloud-shrouded peak. In this high-altitude terrain, paniolo ride herd on the 30,000-acre Ulupalakua Ranch, in the hills above Wailea, and on Haleakala Ranch, which centers on the town of Kula. One of the area’s major attractions is the “cowboy town” of Makawao, an unlikely mix of ranchers, hippies, mountain bikers, artists and real estate brokers, and home to many of Maui’s best eateries and galleries.
WAILEA The popular South Maui destination is a land of posh resorts, manicured golf courses, upscale retail, dining and, one can confidently say, the island’s best beaches. Here, expanses of immaculate sand, ultramarine waters and lazily swaying palms are the stuff of those proverbial “get away from it all” dreams. There is prime snorkeling and unrivalled views of Kahoolawe and Molokini, while the coastal walk between Mokapu and Polo Beaches is a great way to experience the area without getting into your car.