Catch the Wave: Hawaii’s Most Exciting Paddling Destinations

Separating the islands of Maui and Molokai—at little more than eight miles at its narrowest point—the Pailolo Channel is one of the windiest in the Hawaiian Islands. This means swimming and water sports in and around the channel are only for the very experienced. Some believe that Pailolo combines pai (lift) and olo’olo (shifting), while others say the name means “crazy fisherman,” in reference to the rough sea conditions. The annual Pailolo Challenge, held in September, is a 26-mile course from D.T. Fleming Beach Park on Maui to Kaunakakai Pier on Molokai—one of Hawaii’s best downwind runs.

Maui’s North Shore lures surfers for its big open ocean swells—and has a notable draw for paddlers too. Along the Maliko Downwind Run, consistent winds allow paddlers to zip atop the ocean’s surface with 20-25 knot winds at their backs. Considered by some to be a magic carpet ride when it comes to downwinders, the full eight-mile run begins in Maliko Gulch and ends in Kahului Harbor (where smart paddlers stash their shuttle vehicles). Each May, some of the world’s best SUP and outrigger canoe paddlers race this legendary downwinder during the OluKai Ho’olaule’a, a celebration of Hawaiian spirit.

Swift streams and waterfalls continue to carve these vertiginous and rugged valleys as they pour into the sea. One of the most stunning wilderness areas on earth, it also contains ancient Hawaiian ruins of graves, temples, house platforms, and terraced fields. The fear factor increases past the initial two-mile path to Hanakāpīʻai Beach (best visited in summertime, as winter swells tend to wash it away). Only experienced hikers in good condition and with proper gear should venture further along the famous 11-mile Kalalau Trail. Check for path and park closures before making plans and don’t forget the $20/night permit to crash at a campsite. However long you trek, stay on the main path and pack out what you brought in.