On the southern shoulder of Haleakala is Ulupalakua Ranch, a 20,000-acre spread once owned by legendary sea captain James Makee, celebrated in the Hawaiian song and dance Hula O Makee. Wounded in a Honolulu waterfront brawl in 1843, Makee moved to Maui and bought Ulupalakua. He renamed it Rose Ranch, planted sugar as a cash crop, and grew rich. Still in operation, the ranch is now home to Maui's only winery, established in 1974 by Napa vintner Emil Tedeschi, who began growing California and European grapes here and producing serious still and sparkling wines, plus a silly wine made of pineapple juice. The rustic grounds are the perfect place for a picnic. Pack a basket before you go, but don't BYOB: There's plenty of great wine to enjoy at Tedeschi. Settle in under the sprawling camphor tree, pop the cork on a Blanc du Blanc, and toast your good fortune in being here.

Across from the winery are the remains of the three smokestacks of the Makee Sugar Mill, built in 1878. This is home to Maui artist Reems Mitchell, who carved the mannequins on the front porch of the Ulupakalua Ranch Store: a Filipino with his fighting cock, a cowboy, a farmhand, and a sea captain, all representing the people of Maui's history.