Note: Online Registration is open and can be accessed at Pailolo Challenge Team Registration 2019.

Can we update registration information later?
You can change the names of your paddlers, division and boat information up to Sunday, Sep 8, 2019 midnight.

What is the race cancellation policy?
Full refunds will be given up to August 13, 2019, less a $25 cancellation fee. No refunds will be given after midnight August 13th.

The Pailolo Challenge race committee will make an assertive effort to produce events as scheduled, however courses and schedules may be modified based on unforeseeable conditions arising from adverse weather, natural disaster and/or Acts of God. If the course has to be changed or the race cancelled due to unforeseeable circumstances beyond our control, there are no refunds, transfers, or rollovers.

Where are the forms?
Find forms here.

When are the forms due?
All crew information -online and paper forms and payments are due no later than Sunday, Sep 9, 2019, midnight.  This means ALL forms, HCRA cards, honorary paddler forms and all waivers, escort forms, escort insurance, vessel check list.  Here’s a handy 2019-Pailolo-REGISTRATION-CHECK-LIST.

How can I pay the crew’s entry fee?
Entry fee is paid at the time you complete online registration. Any remaining balance will be due at one of the the mandatory scheduled race week Crew Check-Ins but absolutely no later than Friday, Sep 13, 2019, 11:00am-3pm Kahana Gateway Plaza.

Note that return Ferry RSVP/payment and Boat towing between shipping facilities and the beach are separate arrangements online and require online payment at the time arrangements are made.

Can I mail in a check for our entry fee?
Yes, entry fee may be mailed to Hawaiian Canoe Club, P.O. Box 5053, Kahului, HI 96733 or hand delivered to Hawaiian Canoe Club. Checks must be RECEIVED no later than Saturday, 9/8/2019 and should be written payable to “Hawaiian Canoe Club”  – if you have issues with paying, email: [email protected]

Why is the iron entry fee higher than the change crews’?
The entry fee is higher to cover the costs for medics, luggage support boats and extra official boats to tend to iron crews in case of emergency and/or injury.

We are an iron crew, can we bring our own Radio?
No, our safety policy requires iron crews to “rent” the Safety Paddler Packs for $100 which is fully refundable if they are returned in full working condition at the Molokai Yacht Club at the conclusion of the race.


We are Hawaiian Canoe Racing Association members, do we need insurance ?
No, all HCRA members are covered by HCRA insurance but we need a copy of your HCRA card and you still need to complete the Pailolo Participant Waiver.

We are out-of-state paddlers, do we need insurance ?
Yes, you can provide a certificate of insurance with the following requirements:
1. All non-participants/non-members of HCRA, an out of state or foreign team will be charged an insurance assessment at registration. Out of state and foreign teams must provide a Certificate of Insurance for Commercial General Liability/Participants Liability with minimum limits of $1,000,000 (US Dollars) for the race.

2. The Certificate must name the following additional insured’s:

  • a) Hawaiian Kamalii, Inc dba Hawaiian Canoe Club,
  • b) Maui County Hawaiian Canoe Association, and
  • c) Hawaiian Canoe Racing Association.

3. Coverage must be current and cover the duration of the event.

We are not HCRA members and don’t have our own insurance, How can we be covered?
You can become honorary HCRA members for $22 each paddler. You will need to complete an HCRA waiver, fill out an HCRA-Honorary-Paddler-Form, pay the $22 coverage and provide a valid license or passport. This also will cover Na Wahine O Ke Kai and Moloka’i Hoe.


We are an out-of-state crew, how do we secure a canoe?
Specify that you need help on your registration. We will do as best as we can to help you secure a canoe rental. The chances of getting a Bradley Lightning or Unlimited canoe are slim. We suggest you contact crews going to Na Wahine or Moloka’i Hoe who are NOT doing the Pailolo Challenge. They need their canoe on Moloka’i. Your crew pays for shipping to Maui and you paddle it to Moloka’i.  Although we will provide assistance to secure canoes, the race committee is NOT responsible for securing canoes.

We are shipping our canoe to Maui, how will it get to the start of the race?
We will take care of that for $75! You will need to arrange for and pay for this service online. See the “Accommodations Page” on this site. The Towing arrangements page is located here.  Please ship your canoe to Ka’ili Moikeha (contact information in the following question). Please pre pay for shipping. We will NOT pick up canoes that are not paid for. When it arrives on Maui, Young Brothers. Ltd will call us, we will pick up and store at Hawaiian Canoe Club’s property at Kahului Harbor. All canoes will the towed to the start of the race (D.T. Fleming Beach) by Friday, Sept 13, 2019.

Who do we ship our canoe to?
 Ka’ili Moikeha, Hawaiian Canoe Club, Pailolo Challenge (808) 893-2124.
** the bill of lading must identify the canoe name and crew team name
You must pre-pay for shipping. We will NOT pick up canoes that are COD (Collect-On-Delivery).
**Special Note: PLEASE SHIP ON CARPET. All canoes shipped on tires will be charged $50 disposal fee**

When do we ship our canoe?
Your canoe needs to be on Maui, ready to pick up no later than Wednesday, September 11, 2019. We will not pick up from Young Brothers on Thursday, September 12 nor Friday, September 13.

We will be doing Na Wahine O Ke Kai or Moloka’i Hoe, how will our canoe get to Hale O Lono?
At the time of registration you will specify your post-race canoe destination. We will give you a sticker to put on the canoe, NW (Na Wahine) or MH (Moloka’i Hoe). At the race finish there will be designated, signed areas where to take your canoe. From Kaunakakai, your canoe will be towed to Hale O Lono prior to the following races.

How does our canoe get home after Pailolo if it is NOT getting used for Na Wahine O Ke Kai or Moloka’i Hoe?
Please specify where your canoe needs to be shipped after the race and we will ship it back to you COD.

Can you help us find an escort for the race?
Unfortunately we no longer offer assistance with finding escort boats and drivers.



How many people can be on my Relay Mixed Open crew?
All of the MIXED masters and open crews are allowed UP TO twelve paddlers (with a minimum of 9 paddlers) consisting of at least 50% women. Teams can choose to paddle with as few as 9 or as many as 12 on their crew. The 50% women translates as a minimum of 5 women if you go with a 9 or 10 person crew, or 6 women for an 11 or 12 person crew.

Do we have to have at least three women paddling at all times?
No. Mixed crews can field any combination of paddlers during the race but the team makeup must consist of at least 50% women.

Do we have to race the specified number of paddlers for our division??
No. You can paddle with less paddlers but know that you may be racing against crews that have the specified maximum number of paddlers.

Does our crew need to all wear the same jersey?



Here is a handy Timeline of Race Week 2019.

Sunday, 9/8/19: Midnight:

Wednesday, 9/11/19, 3-5pm

  • CREW CHECK IN for HCC and International Crews (if already arrived). Turn in any outstanding documents & payment balances. Pick up swag bags and race shirts. Pre-Sales of Logo Wear.
  • At Hawaiian Canoe Club (Hoaloha Park in Kahului)
  • NOTE: This is last day YB pick up for Incoming Canoes shipped to Maui for race start.

Thursday, 9/12/19, 4-6pm

  • CREW CHECK IN for all Maui Crews. Turn in any outstanding documents & payment balances. Pick up swag bags & race shirts. Pre-Sales of Logo Wear.
  • At Hawaiian Canoe Club (Hoaloha Park in Kahului)

Friday, 9/13/19

  • 9am-3pm
    • Pailolo Logo Wear Sales
    • At DT Fleming Park (Mile Marker 31.1; Hwy 30 aka Honoapiilani Hwy. Turn on Lower Honoapiilani Rd. to parking at end)
  • 11am-3pm
    • CREW CHECK IN for all crews. Turn in any outstanding documents & payment balances. Pick up swag bags and race shirts. Discounted lunch and beer!
    • At Maui Brewing Company Brew Pub (4405 Honoapiilani Hwy, Lahaina)
  • 5:30 pm
    • COACHES MEETING. THIS IS NOT OPTIONAL. All crews must have at least ONE steersman or coach present. Attendance is mandatory. If a crew is not represented, their entry will be forfeited without refund. BE THERE.
    • BOAT# and post race destination STICKERS and IRON CREW Safety Pack PickUp.
    • At DT Fleming Park (Mile Marker 31.1; Hwy 30 aka Honoapiilani Hwy. Turn on Lower Honoapiilani Rd. to parking at end)

Saturday, 9/14/19: RACE DAY: ALL CREWS at DT Fleming Park (Mile Marker 31.1; Hwy 30 aka Honoapiilani Hwy. Turn on Lower Honoapiilani Rd. to parking at end)

  • 6:30-7:30am
    • Final BOAT rigging
    • IRON CREW BAGGAGE must be on the beach ready for pick up no later than 7:30am.
      Max two bags per crew, no larger than 20-liter Dry Bag and/or Paddle Bag.
  • 7:45am
  • 8:30am
    • 1st RACE START: Women & Mixed Crews
  • 9:00am
    • 2nd RACE START: Men Crews.

There will be a 10 MINUTE PENALTY for not starting in your designated start time.
There will be a 20 MINUTE PENALTY added to crews’ final time to those OVER THE LINE at the Start.



Are the any hotel codes or special rates for racers?
We have NO special racer rates or specials this year for any accommodations/hotels (Maui and Molokai).  We apologize for any miscommunication.

Where can I book the ferry back to Maui after the race?
We have a chartered ferry with limited seats from Kaunakakai, Molokai (leaves 5pm) to Lahaina, Maui. $65 per passenger, pre-paid reservation. The ferry RSVP/payment page is here (link also located on the accommodations page).  [ Sold Out: Sorry all charter seats are taken ]



We are an iron crew without an escort. How does our luggage get from Maui to Moloka’i?
We are offering a water shuttle for baggage (limit 2 bags per crew) for Iron Crews that will be picked up at DT Flemings Beach race morning and dropped off at the race finish.  This year the Iron Crew Entry fee covers luggage/bag transport (maximum 2 bags per Iron Crew). Baggage must be on the beach by 7:30am in order to be accepted for transport.

I’m on an iron crew and will send our canoe’s bag with the baggage shuttle. Where do I drop the bag off ? Who do I pay?
 There will be a designated area at the race start (flag on the beach) to drop your bag off to be shuttled by Jet Ski to a luggage boat. Baggage must be on the beach by 7:30am in order to be accepted for transport.  This year the Iron Crew Entry fee covers luggage/bag transport (maximum 2 bags per Iron Crew; 20-liter dry bag and a paddle bag).

Is there a shuttle from our hotel to the race start?
No. We have listed some taxi and shuttle options HERE. We recommend getting a taxi from your hotel to race start since parking is VERY limited at Flemings.

Is there a shuttle from the race finish to where the ferry leaves?
It is maybe about a quarter of a mile walk but yes, shuttles to the Ferry terminal will be available. After paddling 25-miles, this will be a good cool down for you. If you are so full of ono food and craft Maui Brewing Co Beer, you can jump on the shuttle – for free.  Note that there are limited seats available on the ferry from Kaunakakai, Moloka’i (leaves 5pm) to Lahaina, Maui. $65 per passenger, pre-paid reservation.
Online Ferry RSVP/Payment Form located here. [ Sold Out: Sorry all charter seats are taken ]

What do we do on Moloka’i after the race?
 You have several options!
-Unrig and load your canoes onto the respected trailer, head to the dock to tie it to the pallets if getting shipped back to your island.
-Sit back and enjoy our After Party with live music, awards, lunch and beer provided by Maui Brewing Company
-DON’T MISS YOUR FERRY or FLIGHT! Get on the shuttle to the dock OR
If you are heading to the airport, there is a shuttle $8/person, 4 people minimum.
-Book your room at Hotel Molokai here!


IF YOU HAVE A QUESTION, PLEASE ASK!! email: [email protected]