Aloha! Welcome

The Pailolo Challenge is a 26 mile race from DT Fleming Beach, Maui,  to Kaunakakai, Moloka’i. Paddlers gather from Hawaii, USA, Canada, Australia and more to test themselves in excellent channel crossing conditions.

Since inception the race has caught on and considered to be the most consistent and funnest canoe race in Hawaii. Join us!

Nalu’s Pailolo - 2023 FAQ

The Nalu’s Pailolo 2023 is on! While the Pailolo Channel crossing will continue, it will be with many changes and adjustments. Please read the FAQ if you are considering participation. Planning ahead is key for a safe and sucessful event. Mahalo for your cooperation and support! There are many changes in the 2023 Pailolo Challenge, we are excited to pivot to meet the needs of Molokai community as well as the paddling community. Some highlights below:

  • All crews require an escort (including Iron)
  • No luggage service. No ferry.
  • Maliko race (OC1/OC2,) Sunday – finish at harbor. After party to follow.
  • Entry fees $700 per crew + $35 per paddler over 6
  • HCRA Honorary fees $40
  • Towing Maui $80 – Towing Molokai $60

2023 Maliko Race + Awards & After Party

Maui is home to one of the best downwind runs on the planet, Maliko! We are pleased to offer an additional race day, open to OC1, OC2, & Surfski.

Our goals this year include a light footprint on the Molokai community so we decided to celebrate the Pailolo Race by racing again on Maui, Sunday, with an awards ceremony and celebration following the 9.5-mile Maliko Race.

  • Maliko Run Race – 11a, Sunday, September 17th, 2023
  • Pailolo & Maliko Race Celebration & Awards – Following the Maliko Race (around 1pm)
  • If you raced in Pailolo the day prior, your entry fee is covered
  • More info coming soon!

Mahalo Sponsors

We greatly appreciate the sponsors who support the sport of our ancestors and help us do what we love to do. We hope that you will support them in return by considering their service and products.
If you are interested in sponsoring The Pailolo Challenge, please use the contact form below or complete the Pailolo Sponsorship Proposal

The Worlds Funnest Outrigger Canoe Race

Cross The Channel
Strong Competition
Prepare for Kaiwi
Maliko Race
It’s About Fun

Race Scheduled for September 16th, 2023

Pailolo Race Course

Young Brothers – Canoe Delivery


Mala Boat Ramp




Race Start – DT Fleming Beach


Finish Line – Kaunakakai Harbor


Maui Brewing – Awards and Celebration