The Hawaiian kings knew that Lahaina was the crown jewel of the islands. Which is why this town of 11,700 was once the royal capital of Maui Loa in antiquity. Now it's the charming gateway to Maui's world-famous Ka'anapali and Kapalua beach resorts to the north. Its banyan trees add a courtly air to the downtown, and its brightly colored Front Street, busy with shops and galleries, keeps things lively. Lahaina has nearly perfect air quality, and when you add its dry, sunny climate in a tropical paradise, that makes life pretty ideal.
Long a favored harbor for American whaling vessels, Lahaina maintains an exotic tinge of a mid-19th-century Hawaiian seaport in its architecture and vibe. The seafaring tradition continues each year, when the town hosts the finish of the Vic-Mauo Yacht race, the longest offshore sailboat race on the West Coast, held every June through July.
Where to Stay: Plantation Inn sits in the historic district. Rates start at $158; 800/433-6815 or theplantationinn.com.