Dad can slip on a pair of Maui Rippers board shorts at Simmer Hawaii (137 Hana Hwy.; 808/579-8484). Bikini-wearing moms get outfitted at the chic flagship store of Argentinean designer Tamara Catz (83 Hana Hwy.; 808/579-9184), whose husband is windsurfing world champ Francisco Goya. Hana Hwy Surf (149 Hana Hwy.; 808/579-8999) sells its own brand of junior trunks ($39). Before taking off, lay in a supply of Maui Gold pineapples—available boxed to go at the Kahului Airport—so you can continue the luau back home.
Oahu-based Alex Salkever, a father of two, writes the travel blog Hawaiirama.com.