The iconic Waimea Plantation Cottages at the base of Waimea Canyon feature remodeled plantation houses, some of them dating back to the late 1800s. They’re nestled under a coconut grove along a beach of chocolate-covered sand. In the north, near Hanalei Bay, the five-star St. Regis Princeville has an infinity pool, a 10,000-square-foot spa, and epic views both of the mountains and of the reefs along the resort’s coastline.
Start with a fresh pitaya (dragon fruit) bowl or açaí bowl at Aloha Aina Juice Café, a hole-in-the-wall juice bar. Then head to Blue Hawaiian Helicopter Tours for an hour-long flight—a must-do on an island with craggy geography that makes much of the landscape otherwise inaccessible.
Once you’ve regained your land-legs, drive to Lumahai Beach for a few quick snaps of the very waters where South Pacificwas filmed (because of the undertow, the visitors' bureau warns against taking a dip). From there, it’s a five-minute drive to Hanalei Bay, an area packed with to-die-for fish shacks and food trucks: Take your pick from poi (a porridge-like Polynesian staple made from taro root), roasted pork, tacos, and more.
Sunbathe a bit while you digest, then hit the waves running with a two-hour surf lesson via Hanalei Surf School. They can haul in all your equipment and have you up in no time, with private and semi-private classes every day from 8 a.m. to 4 p.m.
Stop at homebase to wash the sand out of your hair, then return to the area for dinner at the hip Bar Acuda, which serves creative tapas sourced from island fishermen and nearby organic farmers. Finish with a nightcap at Tahiti Nui, a funky tiki bar with live music and just-right mai tais.
Wake up bright and early to explore Waimea Canyon, a ravine 10 miles long and 3,000 feet deep in parts. Formed by a river once rushing off Mount Wai’ale’ale, the island’s central peak, the chasm makes for a beautiful drive, with hiking trails forking off along the canyon and past stunning waterfalls. If yesterday’s surf lesson left you too stiff to march, consider booking the Waimea bicycle downhill tour with Outfitters Kauai. You’ll meet at the crack of dawn either at their storefront in nearby Poipu or at a designated meeting spot in Waimea Town before being shuttled up to the Waimea Canyon Lookout. Then you’ll coast down to sea level, past thick forests and stunning lookout points. Refuel with brunch at Gina’s Anykine Grinds Café (aka Gina’s at Yumi’s aka Grinds Cafe—just go to 9691 Kaumualii Highway).
Round out the weekend with an afternoon near Mahaulepu Beach, on the island’s southeast coast. The Mahaulepu Coastal Trailwinds through a stretch of rugged, undeveloped coastline, past sand dunes, limestone formations, and—if you’re lucky—sea turtles, seals, and whales. Again, hiking isn’t your only option: CJM Country Stables offers two-hour horseback rides through the region, typically at 9:30 a.m. and 2 p.m.
Wrap up a packed day by relaxing in Poipu; Keoki’s Paradise has an “aloha hour” and all the tiki torches your kitschy dreams are made of. End on a more refined note with a reservation at Red Salt, a romantic oceanfront spot serving inventive Hawaiian fare.