1. Kauai Done Right
All too often, visitors to Kauai make the same grievous error: cramming a trip to the tiny town of Hanalei (pop. 470) into a single afternoon. Don't do it. Framed by 3,000-foot cliffs, electric-green taro fields, and a perfect horseshoe bay, the halcyon beach community on Kauai's north shore is quite possibly the sweetest spot in the whole state. Check in to the homey Hanalei Surfboard House Nui and start ticking off the island's less trodden hits (doubles from $195; hanaleisurfboardhouse.com). You might hike sections of the Na Pali Coast's Kalalau Trail, paddle the Hanalei River to the mountain-ringed Hanalei National Wildlife Refuge (kayak rentals from $29; kayakkauai.com), or pedal the Powerline Trail to Wailua (bike rentals from $20; kauaicycle.com). No matter how you play it, you'll still be begging for one more afternoon.
2. Two if By Sea
Every February thousands of humpbacks migrate from the Gulf of Alaska to the warm waters off Maui and Lanai—and there's no better vantage point than the bow of a live-aboard yacht. On Honolulu Sailing Co.'s seven-day skippered sail, you'll cruise from Oahu to Molokai, Lanai, and Maui and dodge breaching whales by the dozens. Megafauna aside, other trip highlights include anchoring at Molokai's pristine Hale o Lono Harbor, prowling Lanai's uninhabited beaches, snorkeling with moray eels along fringing reefs, and hoisting the main for your final, fast, downwind run back to Oahu ($1,400, including bare boating instruction; honsail.com).
3. Maui Top to Bottom
Even if you don't spot Laird ripping waves off Maui's famed North Shore, you're still in for an unforgettable show. Winter swells can top 60 feet, and surfers come from around the world to ride them. Catch the action at Hookipa Beach in the laid-back town of Paia, then head south to hit the water yourself (doubles at the new Paia Inn from $189; paiainn.com). The rollers near Ukumehame and Puamana beaches were made for mortals, and surf instructor Tide Rivers (real name) knows where the waves break best (private lessons from $160; riverstothesea.com). No trip to Maui is complete without a pilgrimage to 10,023-foot Puu Ulaula. Most visitors drive to the cindery summit and hike from there; take it from the coast up instead. Starting at the Kaupo Gap trailhead (eight miles west of the Kipahulu Visitor Center), you can climb 18 miles and 9,000 feet in three days, bunking in rustic cabins along the way ($75 a night; nps.gov/hale).
4. Big Island By Road
Just because it's big doesn't mean you can't see it all. Give the island of Hawaii a giant lap in your rental car. From Hilo, drive northwest along the Hamakua coast to Kukuihaele and park by the 4WD road outside of town. You can hike into the verdant Waipio Valley from there and pick up the Muliwai Trail into back-of-beyond Waimanu Valley (hawaiitrails.org). Then it's on to Waimea, whose Saddle Road climbs 14 miles of switchbacks to the summit of Mauna Kea. Take in the 360-degree view, then wind down to the Kona Coast, where Garden Eel Cove draws 150-plus manta rays after dark (night dives from $95; konahonudivers.com). Last stop: Hawaii Volcanoes National Park. Motor out to the Jaggar Museum overlook for a close-up view of Kilauea, which has been burbling lava since 1983 (nps.gov/havo).
Insider Tips: You can't visit the birthplace of stand-up paddleboarding without giving the sport a shot. Most surf shops offer lessons, but choose carefully. "People who used to teach surfing think they can become SUP instructors, but they don’t have the expertise," says pro Maria Souza. Her Maui outfit teaches proper technique and etiquette—surfers have the right of way! (from $159; standuppaddlesurf.net)