For the perfect sunset stroll, take the 1.3-mile shoreline path that connects Wailea’s beaches and the resort hotels that front them. The undulating path winds above jagged lava points and back down to the sandy shore.
In winter this is a fantastic location for spotting humpback whales. On a good day you may be able to see more than a dozen of them frolicking offshore.
Some of the luxury hotels you’ll pass along the walk are worth strolling through as well, most notably the Grand Wailea Resort, which is adorned with $35-million-worth of eye-catching international works of art. Stop by for one-hour art collection tours on Tuesdays and Fridays at 10am, which begin at the Na Pua gallery.
In front of the Wailea Point condos, you’ll find the foundations of three Hawaiian house sites dating to 1300 CE; this is also a fine spot to watch the sun drop into the sea.