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!

Pailolo is going green. We are taking extra measures to be more environmentally conscious. Majority of our registration process is now handled online, electronically. Unfortunately for legal reason, we do still need hard copies of certain waivers and paperwork.

At the after party, there will be waste stations with compost, recyclables, and trash. The Maui Huliau Foundation will be training Moloka’i High School athletes on proper management of these stations. All of the lunch products have been donated by Sustainable Island Products and are 100% compostable. Sustainable Moloka’i will be using the compost at their local farm.  All of the Maui Brewing Co beer cans will be recycled and redeemed for funds for the high school athletes.

We also discourage canoes to be shipped on tires. We ship our canoes on rolled, used carpet.

We hope that you take part in this initiative and minimize your waste! We discourage single use plastic water bottles and promote reef-safe sunscreen.

Mahalo to Hawaiian Paddle Sports for supporting this initiative and coming aboard as a sponsor!!


Whether you are traveling from Hilo or Hong Kong, what makes you come back to race the Pailolo Challenge?

Growing up as a paddler, there were always certain distance races that stuck out: Queen Lili’oukalani, Catalina, Na Wahine O Ke Kai and Moloka’i Hoe. Not until the past decade, has the Pailolo Challenge been a top option for 6-man distance races. In the 1970-90’s, it was a run that my grandparents used to do to get their canoes over to Moloka’i for the Ka’iwi Channel races. They said it was such a fun training race; good preparation for the following weekend.

Now, fast forward to 2017. The Pailolo Challenge is right up there will those renown races and paddlers’ favorite run!

We are thrilled to be a top option for all distance paddlers! Each race offers something different. Whether it be tradition, the mental challenge, the party, the conditions, the merchandise… Everyone has their favorite.

The two top reasons why crews return to the Pailolo Challenge: SURF & MAUI BREWING CO BEER. Duh.

As paddlers and race coordinators, we know how how difficult paddling, coaching, fundraising, and managing a crew can be and we hope that we can make the process as easy as possible for you! We want ALOHA to also be a top reason why you love the Pailolo Challenge.

Maui No Ka ‘Oi = Maui is the Best!

If you are coming to Maui a little early I have some suggestions for things to do while you are here preparing for your race.

Maui is a beautiful island and did you know that you can go paddle, be active and enjoy the ocean without training and hurting? Check out Hawaiian Paddle Sports while you are here. There are canoe and snorkel tours, SUP & surfing lessons and canoe surfing if the weather is right. The Eco-Friendly Hawaiian Paddle Sports is one of the highest rating tour companies on Maui. Call to make reservations!

Another favorite of mine is Tobi’s Shave Ice. Fresh fish and shave ice. Can you go wrong? Plus Pa’ia is a cool little town to check out while you explore the island.

A few other must do’s (more like my “must eats”):

  • Tinroof – Whatever Chef Sheldon is making
  • 808 on Main – Kula Strawberry Salad, add avocado, sub feta for goat cheese
  • Like Poke? Food Truck – Poke bake or whatever isn’t already sold out!
  • Cafe O Lei – Fish Special, French Onion Soup
  • Maui Brewing Co – Everything; I haven’t found something there I don’t like, food or beer. They have 2 locations: Kahana and Kihei. Kahana has a full restaurant, Kihei is a tasting room with usually a really good food truck outside.
  • Baya Bowls – Because everyone loves acai bowls, right?
  • SlappyCakes – It’s so fun.
  • TriPaddle – Just in case you forgot anything for your race.
  • Ali’i Kula Lavender – Maui is more than beaches and waterfalls. Visit this serene lavender farm up Haleakala Mountain. Best to go in the morning before the fog or rain rolls in.
  • Maui Thing – A great place to pick up locally made gifts for your friends back home.

These are just a few of my favorite things on Maui that make it no ka ‘oi.

“It’s Aloha Friday, no work til Monday….”

Yeah, no such thing in a paddler’s life. Weekends is when we put in work.

With race day just over a week away, things are crazy. Emails flooding in, phone is ringing all day, logistics are getting hectic, basically… people are freaking out. In the midst of all the craziness, I am reminded that it is Aloha Friday.

Aloha” means much more than a greeting or expression of love; it is a way of life. It is harmony, humility, and honesty; it is patience and kindness.

For everyone being burdened by the stresses of life or race preparation, just take a minute and remember the reason why you are doing it all. We all have our own purpose and reasons.

Enjoy your weekend. Good luck to those racing to and from Catalina Island in California. We will see you soon!

Maui Beer

I have gone through phases of beer snobbery. I got sucked into uprising of craft brew beer while living in Southern California a few years back. I was a college graduate, too good for Natty Light; now I smell my beer before I drink it, “Does it have good head?”

Some of my best friendships and paddling connections have been made with other paddlers and teams over a good, cold beer after a race. I think many of you can say, “Yes, you’re right. I met [you] after [Pailolo] while drinking a Bikini Blonde or Big Swell IPA.”

Once I really got back into competitive outrigger canoe paddling, I realized that the best kind of beer after a race is “a cold one.” But it’s one thing to have a cold beer after a race and it’s a whole other thing to have a good, quality beer after a race and I prefer the latter.

Maui Brewing Co has been a sponsor and supporter of the Pailolo Challenge from the beginning. They open up their Brew Pub in Kahana for our crew check in/registration day every year. Food and beverage discounts run throughout the day for our racers. MBC also provides all the beer for the after party on Moloka’i. With celebrating our 10th Anniversary, we have ordered 10 ADDITIONAL cases of MBC beer for YOU! (Don’t worry, if you don’t drink, we have you covered as well with some MBC Root Beer which is equally delicious.)

maui jim pailolo

Growing up in Hawai’i, especially doing water sports, we are used to seeing pterygiums on our friends’ eyes and unfortunately, usually in the mirror. Both of my parents have it and mine became noticeable when I was 18.


You can get surgery to remove it, but I kind of like mine. When I lived on the mainland, that is how I knew people were making eye contact. They would zoom in on my eye and ask what it was. When I see others with a “googly” I know we have something in common: a love for the ocean.  But it also has its cons. Any time I surf or paddle without sunglasses, I am left with irritated, itchy, painful, red eyes.

The best thing to do: WEAR SUNGLASSES.

We are excited to have Maui Jim as the title sponsor for the 10th Annual Pailolo Challenge!

Maui Jim is known to be one of the highest quality sunglasses on the market. They began in 1980 as a small company right here on Maui in Lahaina, just a few miles from the start of the Pailolo Challenge.


“Inspired by the beauty and culture of Maui, our mission is to spread aloha through vivid color, clarity, and detail.
For those who appreciate the sun, Maui Jim provides more vibrant colors of the world while protecting your eyes from the harsh effects of glare and harmful rays.
We make your life brighter so you see the colors of your world at their best and always feel confident in your style. 
Maui Jim believes color and light are the key to human experience. Our sunglasses show you its full spectrum, so you can see the world like you’ve never seen. We believe everyone should experience all 16,777,216 hues of beautiful color that surrounds us every day. “

We are thrilled to have the support of such a quality company. Not only do they produce quality polarized lenses and eye protection, they are quite stylish and beneficial on the ocean.

Check out their shop online to pick out your next Maui Jim sunnies to protect your eyes and pterygiums!

Last year when I did an interview with Hawaii Public Radio about the race, I was asked, “How did you get involved with paddling?” I was not prepared for the question but it was the first time I had to think about that question. “I didn’t really have a choice,” I answered.

What do you do when you can’t find someone to watch your kid while you race? (Sorry, we do not provide childcare during the Pailolo Challenge……yet.)

My grandparents were coaches for Kihei Canoe Club from 1970s through 1990s, my mom started paddling before she knew her time tables and I was just born in to it. There has never been a question about what we were doing during summer. I started paddling with Hawaiian Canoe Club at 10 years and every summer until I went to college on the mainland. After college, I was living in California and started paddling for Oceanside Outrigger and Newport Aquatic Center. I found a whole new paddling family on the mainland and fell in love with the sport all over again. In 2012, I was contemplating moving home to Maui and decided to put together a crew for the Pailolo Challenge. It was made of up paddlers from Hawai’i, California, and Australia. We needed a canoe, an escort, hotel room, car, return to Maui – the works. Of course, my Maui family came through and helped me with a lot. As soon as we landed, we went straight to HCC hale to load canoes and kokua my home club, tow canoes to Flemings and help my mom and then current race coordinator, Kaimana Brummel, with registration at Maui Brewing Co.  The race was “the funnest” and I was hooked. Not even 6 months after the race I moved home and less than 6 months after that I was on the Pailolo Challenge Race Committee. The rest is history… When I first came for the Pailolo Challenge, I expected my family and home club to come through to help with accommodations and logistics. Of course the help was going to be different from any other race I had competed in. But then I realized it wasn’t just because I knew the right people, they did this for everyone! The Race Committee is dedicated to making the race fun and accommodating for racers. Just as I was treated as family, we hope that all crews and participants feel the same way. We do live in Hawai’i. You need something, you call your aunty’s friend’s uncle’s dentist’s cousin, and you get what you’re looking for. That “easy.”

HCC Open Women 2013 PailoloHawaiian Canoe Club Open Women 1 in Pailolo 2013. Arianna (daughter) in seat 5 and Theresa Gerry (mother) in seat 4. (I guess she still couldn’t find someone to watch me while she raced.)

Much like every paddler knows, this is not just a sport or a hobby. We are Board Member, coaches, volunteers, fund raisers, competitors, confidants, friends, a team, and even greater, a family. It is a lifestyle. We don’t really go on “vacations,” we visit other places when there are races happening. We budget our annual expenses to pay for entry fees and flights, maybe a new paddle or OC1. Our drawers are filled with colorful tights and jerseys, not to mention the unreasonable amount of trucker hats. It only makes sense that the people we paddle with are still the people we surround ourselves with away from practice and travel with to an island in the middle of the Pacific Ocean. As I found through coordinating this race, my paddling ‘ohana now extends over the entire globe. Mine; yours. Thank you for participating in the Pailolo Challenge this year. If you are a returning participant, I am pleased you decided to join us again. If this is your first crossing, please enjoy yourself and have fun!!!

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