Year-round good weather typifies this increasingly popular side of Maui, which runs down the south coast from Maalaea to Makena, with Kihei and Wailea between them. But because it is the sunny, dry side of the island, South Maui used to be unsightly scrubland until ambitious development over the last 20 to 30 years transformed it—or at least parts of it—into a beauty.

The most upscale area is Wailea, a well-manicured resort along 1 1/2 miles of this coastline. Here, you can get quite comfortable in the island’s most exclusive hotels and condominiums, most of them beachfront, but some up on the gentle slopes of Haleakala. Everything else about this resort is gold star as well. Its five crescent-shaped beaches are about as dreamy as you can imagine. At the Shops at Wailea, many high-end retailers cater to the rich with top-of-the-line designer goods. And steep greens fees are probably the only complaints you’ll hear about the three championship golf courses.

If laid-back sophistication appeals to you but Wailea seems a little too busy, drive right past it to neighboring Makena. It’s more private, with just one luxury hotel (the Maui Prince) and a few condominiums, and also offers spectacular fairways. Robert Trent Jones Jr. designed both of its courses, which golfers rave about.

Other than what you find in the hotels, there aren’t many restaurants and nightclubs in these two resorts. Kihei, just north of Wailea, has a few, though—mostly along its main drag, Kihei Road. This coastal community isn’t highbrow or all that gussied up, so it stands in stark contrast to Wailea. Still, budget-minded travelers favor its moderately priced hotels and condominiums, most of which are an easy walk from the town’s beaches.

Up the coast a few miles, tiny Maalaea is beginning to grow, thanks mainly to its small harbor. From here, many visitors staying on this side on the island climb aboard boats for all types of water fun, from snorkeling trips to whale-watching cruises. It’s also home to the Maui Ocean Center, the island’s aquarium.