Save the Date! We are excited to announce that the Pailolo Challenge is back on after a years’ long hiatus, we can’t wait to see you all there!

WHAT: The Pailolo Challenge is a 26-mile downwind race across the Pailolo Channel from Maui to Molokai

WHERE: DT Fleming Beach, Maui, to Kaunakakai, Moloka’i


Online Registration in state: Link to Hawaii Registration Form

Online Registration out of state: Link to Non-Hawaii Registration Form


Please download and review the Race Packet, Rules, Timeline and Safety Management Plan before registration

New exciting update to 2023 Pailolo

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 Hawai’i. 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!

As we all know, there are many factors that can have a negative affect our racing experience: equipment failure, poor nutrition, bad attitudes, or physical injuries. These are all things that we have somewhat control over and can prepare for. One thing that can have a HUGE impact, good and bad, on our race experience is the weather. Our sport relies on the weather conditions. We can have all our ducks in a row, perfect preparation, positive attitudes and we show up to the race and it is dead flat and not even a wisp of wind. But even with those kind of conditions, we still go out and charge. It’s just going to be HOT and definitely not as fun, but we go.

We all hope for wind and swells but there is a thin line between fun and dangerous. The Na Wahine O Ke Kai Race Officials were put in this exact position in 2015 and cancelled the most prestigious race in the Hawaii distance schedule. As race organizers, the safety of our paddlers is our number one priority. If we believe the conditions to be too dangerous for our paddlers, we will cancel the event. A similar situation arose in July 2016 when multiple associations’ Championship regattas were cancelled due to Storm Darby. In this case, permits were revoked from all events during the storm; completely out of race officials’ hands. In August 2016 after Darby, our Hawaiian Canoe Racing Association State Championship was also in limbo. It was not the weather conditions, but the quality of the water we would be paddling in. Officials did everything in their power to ensure a race for the paddlers. I applaud their efforts and commitment.

The Queen Lili’uokalani Race in Kona is this weekend. I do not envy the race coordinators preparing for the largest canoe race in the world as Hurricane Lester lingers just a few hundred miles away. I know they will do their best and make the smartest decisions for their paddlers.

As it seems like these type of situations have recently increased, the 2016 Pailolo Challenge Race Committee took a lot of time and consideration regarding how we would go about things if we were put in that situation. Our cancellation policy is stated on the website. With all event coordination, there are race expenses that are not refundable. This is why we have also stated that entry fees are non-refundable.

The Pailolo Challenge is unique in the fact that we are very limited by space. If you have done the race before, you know how tight the finish line is at Kaunakakai Harbor. We have reached capacity and the number of canoes and people the space can accommodate. We have also seen a increase in our race’s popularity. With the high demand and limited space, we have to ensure that registering crews are committed to racing, rather than holding a spot and dropping out over a crew who may not have made the cut off but had the funds and paddlers ready to race. This is another reason why entry fees are non-refundable.


We have two weeks until race day and there are no hurricanes or tropical storms in the forecast. As of today, we are looking at 15-20mph NE winds and some swells! Of course, nature has its own ways and can change in an instant.

Please check our Facebook Page and website for any race updates. Any and all race updates will be made directly on the website and FB. If it is not posted there, it is not true.

The 10th Annual Pailolo Challenge will be on September 17, 2016.

Registration will open in Spring 2016.

We look forward to another great year celebrating a decade worth of fun!

If you are interested in supporting or sponsoring this event, please email [email protected] or comment on this post.

Another great thing about racing is the swag!

We are very excited about this year’s participant shirts!

Mahalo to Jaclynn Sabado of Paradise Now Hawaii for making a vision come to life!

What a great design…

2015 Pailolo Participant Shirt

Mahalo to the Office of Hawaiian Affairs and our other sponsors for supporting the Pailolo Challenge 2015!

We will also include Redbull for all paddlers and stickers from Palafamala Custom Paddles and a reusable bag from State Farm Agent Kit Okazaki.

Logo wear will be for purchase at DT Fleming on Friday, 9/18, 8am-3pm. Cash and credit card are accepted. Please no personal checks. The price list can be found here.

If there is anything left to sell, we will be taking it to race finish and selling at the after party.

Bring your cash! There will be vendors and massage therapists at the after party. Great time for recovery, buying gifts and supporting the local economy.


The first shipment of canoes have arrived on Maui and the beer has been shipped to Moloka’i!

We are looking forward to hosting the largest Pailolo Challenge to date with approximately 100 crews!

It has been a whirlwind of emails, texts, and calls. I got my first office visit from the M’Ozzies yesterday. They are a 40 women’s crew from Australia. They are repeat competitors and great to see them back on Maui. It is our pleasure to host a race that people want to race again, year after year!

In addition to all the returning crews, we are welcoming a handful of international crews from Singapore, Canada, Australia, and New Zealand. Not to mention our faithful crews from Hawaii. First women’s crew over the line in 2014, 2014 Na Wahine O Ke Kai 40 Master Winners and 5th Place overall finishers Team Revolusun/Hui Nalu/Mike’s Hard Lemonade will return to the Pailolo Challenge 2015.  The women’s masters’ division have some great competition this year with some of the top women in the state: Kailua, Puna, Hawaiian, Wa’akapaemua, Kihei, and Lae Ula O Kai, just to mention a few. We expect some of our top men’s finishes from Hui o Mana Ka Pu’uwai from Kaua’i, Lae Ula O Kai, Wailea and Hawaiian Canoe Club of Maui, Big Island’s Puna Canoe Club, and Moloka’i’s own, Wa’akapaemua. I think we will get some great competition from visiting California teams like Newport Aquatic Center and Outrigger Team California.

With just over a week away our logo wear will be arriving soon! Logo wear sale will be at Flemings on Friday 8am-12Noon. A price list will be available early next week.

As much as we look forward to racing, we equally look forward to finishing!!

You can ask almost every paddler what their favorite thing to have after a race and they will answer with, “Beer.” We hear you and we have your back!

Maui Brewing Co. returns as a top sponsor in 2015 providing our participants with some of their top beverages: Bikini Blonde, Big Swell IPA, and Root Beer for our non-alcoholic drinkers.

A great plate lunch will be prepared and served by Moloka’i Athletic Booster Clubs: Girls’ Softball & Boys’ Volleyball

  • Shoyu Chicken, rice, green sala, sweet potato, papaya, cake, jello
  • Tofu Salad & tomato for you vegetarians!

26 miles is not a short race! We will have 3 massage therapists to work on your bodies, available from 1pm-3pm. Tips are greatly appreciated!

There will be a variety of local vendors set up at the after party: paddling gear, clothing, jewelry, local products. The days prior to the race are quite hectic. This is great opportunity for all of our out of state paddlers to pick up some souvenirs or gifts. Don’t forget your cash!

Throughout the hours after crossing the line, eating, drinking, and having a good time with your fellow paddlers, there will be a live band and awards’ ceremony.

There is a shuttle that is heading out to the pier for those on the ferry, as well as an airport shuttle. The airport shuttle requires a reservation which can be made here: Airport Shuttle.

With just over a week away, we are looking forward sharing a cold one with you all!

Just over three weeks out from race day and things are moving along smoothly.

Registration is filling up, logo wear is being shipped and printed, hotel rooms are booked, flights are made, ferry is sold out!

We are looking forward to seeing everyone in a few weeks.

We would like to thank our sponsors:
County of Maui
Hawaii Tourism Authority
Maui Brewing Company
Office of Hawaiian Affairs
Hawaiian Canoe Club
Alexander & Baldwin
Tobi’s Shave Ice
Adventure Sports Maui
Kit Okazaki, State Farm


We greatly appreciate the sponsors who support the sport of our ancestors and help us do what we love to do. We hope you will support these sponsors, in return by considering their service and products. Mahalo.

If you are interested in sponsoring The Pailolo Challenge, please use the contact form below.


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