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Exploring the Island of Maui During Wintertime

The island of Maui is a treasure trove of unforgettable Adventures just waiting to be found. From the extraordinary and unheralded surf conditions to the vast underwater world begging to be explored, no matter what your style, there’s something for everyone. That’s exactly why we paid a visit to our very own Maui guides Ben Zyons, Don Shearer, Connor Baxter, and many other friends during the holiday break and asked them to help us conquer the island.

Our friends from Enjoy the Maui Life and Maui Cyclery were kind enough to take us on a couple of memorable bike rides. We started with the flat, family-friendly trails in the Koolau Forest Reserve and worked our way to the more challenging Haleakala ride. The summit to Haleakala is one of the island’s most popular rides and it’s easy to see why. There’s something about conquering a steep, 4-5 hour climb that gets the heart rate going and makes us feel superhuman. 

Recognize the yellow helicopter in back? If you’ve ever watched the World Surf League JAWS competition stream or looked at the event photos, odds are you’ve seen this ride. Don Shearer is the pilot and we were somehow able to convince him that it’d be a good idea to take us up for a quick ride. Overlooking the Hawaiian island in a cramped helicopter with our closest friends and looking around to see everyone expressing a combination of fear and pure joy was something we’ll never forget. Our only regret was not capturing it all on camera. 

Foil Adventures are our bread and butter, but getting to ride alongside Connor Baxter, a.k.a “The Greatest Paddler of the Decade”, was truly something epic. The ocean is literally his playground and Connor was cool enough to take us to visit a few of his most secret spots with some of the clearest water we’ve ever seen! We also got to see Connor do what he does best on a board and even came away with a few tips on how to become better paddlers.

The last Adventure we embarked on during our time on the island was free diving with Ben Zyons. Even with our watersports background, practicing different breath holds for time was still a challenge. However, with a few tips and tons of support, we were able to push far beyond what we originally thought possible. And although we didn’t go on 100-foot dives like Ben, we did make it past the one minute mark on a single breath during a few tries. 

Overall, we’d say the 2020 AIO // Maui Adventure was a huge success! A huge thanks to the raddest group of guides on the island. If you’re looking for a Maui experience that’s unlike anything else offered, hit up our guides on the Adventure IO app!


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