Lahaina

This historic town on Maui's western coast used to be a major port of call for whaling vessels—at the peak of the era in the 1800s, some 500 whaling ships came into the harbor here each year. These days, Lahaina is the island's defacto whale-watch capital (such recommended outfitters as the Pacific Whale Foundation have their headquarters there), and the beaches with gentle surf makes it a great spot for beginner surfing classes. As is to be expected from a major tourist hub, the shopping is mostly dominated by Tshirt and souvenir shops (ABC Store is the Hawaiian go-to for Aloha-themed tchotchkes).

But there are a couple of good boutiques not to miss if you're spending some time in the town; most are located along Front Street: Maui Hands Center (#612) for island-made crafts; Tilly Timms (#703) for super-soft graphic tees with Hawaiian themes, including for children and babies; Lahaian Printsellers (#764) for antique maps and Hale Zen Home (180 Dickenson Street) for gifts, children's clothes and decorative items.

Make a point to visit the Lahaina Arts Society (648 Wharf St #103; 808-661-0111), the town's oldest gallery in the historic Old Courthouse. Representing 142 local artists in disciplines including pottery, printmaking and jewelry making, the Society is an active group that also holds regular classes in everything from dancing to lei making. If you want to see all that’s there, go from 6:00 pm to 9:00 pm on Friday, when the town hosts Art Night. Gallery owners and artists come out to meet the public, and there’s live entertainment and drinks.