THE PAILOLO CHALLENGE IS BACK.
Separating the islands of Maui and Molokai, at just over 8 miles at its narrowest point, the Pailolo Channel is one of the windiest in all of Hawaiʻi. Get your crews and canoes ready for one of the most challenging channel crossing races in the Hawaiian islands, which has been nicknamed “the world's funnest canoe race”.
We’re here to help take care of the logistics, while you get to focus on the fun and excitement that the Pailolo Channel has to offer.
Fun aside, we are honored to host this race once again, and preserve the culture and tradition of those who came before us. We hope you have the opportunity to connect with the essence of the channel, the ocean, the Hawaiian islands, and the people.
Mahalo to our sponsors and supporters - with their help we hope to make this the best Pailolo yet! More info to come about race day logistics, hotel discounts, and an after party to remember. We hope to see you here on Maui this September!
Save the Date! We are excited to announce that the Pailolo Challenge is back on after a five-year hiatus. We can’t wait to see you all there!
WHAT: The 2025 Nalu’s South Shore Grill Pailolo Challenge – a 26-mile downwind race across the Pailolo Channel from Maui to Molokai
WHERE: DT Fleming Beach, Maui to Kaunakakai, Moloka’i
WHEN: Race Date – Saturday, September 13, 2025
