SUJ: How long did you prepare for your crossing from inspiration to completion? What did preparation look like? How did you train?

Bobo: Staring at a map last September, I was thinking about crossing all the channels in the Hawaiian islands over the course of a few days. But I decided to focus on only one, the Alenuihaha, after getting advice from my coach, Suzie Cooney. At first, 43 miles seemed like a lot in one shot. It is a straight, broad-reach trek across the Alenuihaha channel all the way from the Big Island to Maui. Yet, weekly training runs on Maliko (the famous downwind trek on Maui’s north shore) made it seem more doable.

My first training run on the Maliko, I remember, took 49 minutes. It went down from there, from 45 to 39 to 29 minutes. I would also wing a lot in Kahului harbor (that’s where the Maliko run finishes) to get in more miles and get the feel of going cross-wind. The most miles I remember doing in a day was 35, which consisted of two Maliko runs and a lot of miles in the Harbor.

Before the Alenuihaha crossing, my family filmed several interviews for “A Boy’s Journey: Crossing the Alenuihaha”. The interviews were all about my crossing, equipment, and training. We interviewed my board shaper, Sky Solbach from Fanatic and Ken Winner, creator of the Duotone wing, who readied my gear for me and also did several training runs. We interviewed Matt Smith, my boat captain also my friend, coach, and mentor Suzie Cooney. It was important to also include my water and Hawaiian mentor, Archie Kalepa who has taught me so much, and Kai Lenny, who really helped me mentally prepare by talking about things like what the channel is like, what to eat the day of the crossing, and possibly what to expect over such a long way over the water.

SUJ: Tell us about the equipment you were riding, board specs and wing size. Why did you choose this equipment?

Bobo: My equipment totally prepared me to cross the channel. I rode a 3’2 Fanatic Sky Wing board, custom made for my size. It is also great for jumps and I was super excited about getting to jump in the channel.

My 3.3 meter Duotone Echo Wing carried me for the entire journey without having to be re-pumped once I started. That is my “go-to” wing size whether it is an Echo or a Unit. It's the size I always use.

My boom was custom made, by Ken Winner, for my smaller hands. And the Duotone Daytona 105, a kite-racing Hydrofoil, which has an unusually small front wing (about 500 sq. cm) and a very tall mast (105 cm), enabled me to fly through the open ocean swells of the channel and jump for the sky. The Duotone/Fanatic team made this journey possible.

SUJ: What was the most challenging part of your crossing? When did you feel the lowest? What did you say to yourself to keep going?

Bobo: My hands felt the crossing. We joked on the boat that I had, “channel hands” as I had a lot of blisters.

Throughout the crossing, I just kept thinking of things I would get at the finish line, like food and lunch, to motivate myself. I made small goals for myself during the Crossing like “Get to where you can see Maui”, “Look where you can see the windmills” and “Start going upwind” or “Start going downwind”.

I felt really prepared. I never felt like I wanted to stop. It did seem long in some spots, especially in the middle of the channel. We had to work on the timing of the boat relative to my speed. The boat had to punch through the swells where I got to go over them a lot.

There were a couple of moments where I just looked around and saw the birds that were jibing and tacking and how they would go up high and do a circle to go upwind. It was really amazing to watch the sea birds. I tried to jump with one of them. I also saw a lot of jumping fish. The Alenuihaha felt more detached from land than other channels I have been in before. For a while, I couldn’t see either island. That was also very cool.

Getting close to Maui was another moment…it was great to do something I had been visualizing in my head for a while and ride the channel.

What did it feel like to get to the end? It was a surprising end because the wind died completely. I had gotten into the boat inside Keoneʻōʻio Bay (La Perouse) but I really wanted to ride through to the parking lot. Captain Matt said, ‘Here comes a gust of wind!” so I jumped into the water and - sure enough - the gust came and I powered up. I was so happy to get as much speed as I could in case the wind went light again. I was pumping most of the time to maintain speed. Sure enough, I got to my finish line. People were honking horns and holding up signs, and just waiting there. It was an amazing moment.

SUJ: Who did you become by completing this journey? Has it changed your outlook on life? How?

Bobo: That’s a little hard to say for sure. I mean, to train for something some people said couldn’t be done, at least by someone my age, and then do it is a great feeling. I think it gets me excited about doing other things like trying longer crossings or going after different channels. It inspires me to think I can dream of doing something and actually accomplish it. I hope my crossing the Alenuihaha does that for other people too.

SUJ: What does being a part of the Maui community mean to you?

Bobo: Being a part of the water community in Maui means everything. When I arrive at the parking lot at Kanaha or Kite Beach, I get excited to see who is there and who I might be in the water with on that day. How great it is to see people you know and be totally inspired to be in the water with the best, most experienced watermen and water women in the world. So many friends and adults have helped with my training, like Josh Riccio and Ken Winner. They made it possible for me to complete the crossing. I need adults with me for safety in the open ocean, and that has meant everything to me because it empowered me to do things I couldn’t have done or even trained for by myself, like crossing the Alenuihaha on a wing or to solo SUP foil the Pailolo channel (Maui2Molokai) last year at age 10, or tandem the event at age 9 with Lara Claydon.

SUJ: How has the Hawaiian culture influenced your lifestyle?

Bobo: I am really thankful to live here on Maui surrounded by the Hawaiian culture. It is cool seeing how Hawaiians lived off the land, built their canoes, and made their own tools. But the biggest aspect of this culture is the attitude of giving and family that I see in people like Archie. I try to take care of the land and especially the ocean. No one wants a dirty ocean. Zane Schweitzer does a lot of beach cleanups as part of his effort to preserve our natural environment.

Channel crossings are a part of life here on Maui. A lot of canoe clubs have OCs that cross over the Pailolo. Before COVID, we had races where we crossed channels. Had I grown up somewhere else, maybe being 5 or 10 miles off shore might seem scarier than it is.

SUJ: What was your favorite moment from your movie release night on Maui? What happened? Who spoke?

Bobo: My favorite moment was the Q & A. It was fun to hang out with my water friends and answer questions. It was also cool to finally watch the movie on the big screen with people. It was my first time watching it all the way through that night. I thought to myself, “It really is a good movie”. My mom and the pastor of our church spoke. I said a few words; there were a lot of people to thank. We also had a live stream interview before the movie where Lara Claydon interviewed me. Coach Suzie, Josh (Riccio) and Victoria, Zane and Kimmie, as well as Scott and Kainani Drexler also got interviewed. We had a photo booth with a specially made movie banner where people could take pictures. So many people came. I was a little overwhelmed. I think like 325 people came and that was during COVID. It was cool to see people come out and support us in this film release.

SUJ: Do you have any future insights into the development of the wing and/or foil? What would you like to see happen in terms of innovations?

Bobo: I see more competitions coming in winging. Freestyle, surfing, down winding and racing all seem close to starting once COVID restrictions are lifted. Foiling is becoming more a part of water sports and more people are enjoying doing it.

SUJ: What’s next for Bobo Gallagher?

Bobo: The channel between Kauai to Oahu (Kaieiewaho) has never been crossed on a wing before. My dad says it's 72 miles. That’s maybe an hour longer than the Alenuihaha. I’d really like to cross all the channels eventually. I also would like to get better at windsurfing and kiting.

I hope contests will start running again in 2021. SUP surfing at the Santa Cruz Paddle fest in March is always fun, and I would like to be a part of the Kite Fest in Maui in June. I’m hoping there will be a wing division there too. The Gorge Paddle Challenge in Hood River, Oregon in August is one of my favorite events each year. I was stoked to prepare for the M2M and the M2O races this past summer before they were cancelled because of COVID. I am super excited for them in 2021.