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.

The groovy-cool town of Paia is always packed, its two-lane central artery mostly a traffic jam. The trick is to come on the early side and to have a plan: breakfast at Café des Amis (42 Baldwin Ave; 808-579-6323) or the leafy Paia Bay Coffee (115 Hana Hwy; 808-579-3111) followed by a couple of hours of shopping, then picking up sandwiches at Paia Gelato (115 Hana Hwy # D; 808-579-9201) or poke bowls at Kuau Store (slightly out of town; 701 Hana Hwy; 808-579-8844) before continuing on to spend the afternoon at Baldwin Beach or Sprecklesville Beach, or to watch the surfers at Hookipa.

Don't expect upscale boutiques: the many glass pipes and tie-die dresses on display attest to the fact that Paia is Maui's hippie central; but it's also not the made-in-China souvenir fare sold in so many other parts of the island. Shops are independently owned and pride themselves for carrying island-made mementos. Don't miss Wings Hawaii (69 Hana Hwy; 808-579-3110) for handcrafted jewelry and ceramics; Tamara Catz (83 Hana Hwy; 808-579-9184) for chic fashion; Alice in Hulaland (19 Baldwin Ave; 808-579-9922) for a wide array of fashion and accessories, as well as kitschy-fun souvenirs; San Lorenzo Bikinis (115 Hana Hwy Unit C; 808-873-7972) and Maui Girl (12 Baldwin Ave; 808-579-9266) for teeny-tiny beachwear and curated Indigo (149 Hana Hwy; 808-579-9199) for breezy dresses, bathing suits and jewelry and crafts that were gathered during the owners' travels throughout southeast Asia.

The most upscale Maui shopping is found at the 64,000-square-foot Shops at Wailea, in walking distance to the Grand Wailea and a short drive from the Four Seasons. The usual suspects are gathered at this al fresco mall: Tiffany & Co., Louis Vuitton, Gucci and Bottega Veneta, but they are surrounded by surf shops like Roxy and Billabong, a Tommy Bahama shop and the Black Pearl Gallery. ABC Store is the go-to-place for all-things souvenirs, from ukuleles, Leis and macadamia nuts to tissue paper printed with hula dancers and postcards with vintage designs.