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North Shore and Upcountry : Itineraries

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  • Morning

    Spend some time away from the sand and surf by heading up the Haleakalā Highway (Route 37) to the coolness of Upcountry Maui. At ’Ulupalakua Ranch you’ll find the Tedeschi Winery. Tours of the winery are free, and you can taste the full range of products in the restored cottage of King David Kalākaua.

    Retrace your path back along Route 37 to visit Makawao, once a cowboy town and now a shopper’s haven. There are tony boutiques and art galleries housed in western-style buildings. Pick up some lunch at Rodeo General Store’s deli or sit down at Duncan’s Coffee Co., both on Baldwin Ave., the town’s “main drag.”

    Afternoon

    Continue down Baldwin Avenue to the Hui No’eau Visual Arts Center. Inside and outside, works by local artists are created, displayed, and sold. Traveling right to the end of Baldwin Avenue will take you to Pā’ia for great people watching – and more shopping. Once a plantation town, then a hippie haven, and now a windsurfing mecca, Pā’ia offers an adventure in browsing for unique clothing at Jagger’s (see Jaggers), work by local artists at Maui Hands, and antiques at Pā’ia Trading Company (see Pā’ia Trading Company).

    For a late afternoon spectacle, the waters off Ho’okipa Beach are filled with the colorful sails of windsurfers and kite boarders. Finally, end your day with a fresh fish dinner at Mama’s Fish House (see Mama’s Fish House).

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