Visitors decked out in the most casual of attire flock to Lahaina to shop, eat, and party—especially along Front Street, which can get quite busy and loud, with lively music blasting from hot night spots such as Cheeseburger in Paradise. Despite its commercialism, however, this village does have a lot of history, which the Lahaina Restoration Foundation has worked diligently to preserve. While making the scene here, seek out the foundation to learn more about Lahaina’s colorful past and its historic buildings, such as the Baldwin House, a missionary’s home built in the 1830s.

To the north of Lahaina are the upscale resorts of Kaanapali and Kapalua. In Kaanapali, six luxury hotels and four condominium complexes front a sparkling 3-mile-long beach with breathtaking views of Lanai and Molokai. Complementing the above-average accommodations are two championship golf courses and Whalers Village, an open-air shopping center with distinctive shops such as Gucci and Prada and oceanfront restaurants that serve up fun along with their food.

Down the road a ways, the little more exclusive Kapalua spoils visitors in high style with two blissful waterfront hotels and a group of comfortable villas spread out over the green mountainside. The resort also has three golf courses with gorgeous views and three beaches—the most notable being Kapalua Beach, a heavenly, crescent-shaped stretch of sand with calm, clear water that’s usually good for swimming and snorkeling. Plus, the snorkeling’s excellent in the summer at nearby Honolua Bay, a marine conservation district.

Between Kaanapali and Kapalua are three other low-key seaside resorts—Honokowai, Kahana, and Napili—with beachfront condominiums but not many other amenities.