At Starboard, we believe in chasing dreams across oceans. This year, Tim Oliver did exactly that — crossing the legendary Kaiwi Channel to take the win in the Unlimited division at the 2025 Molokai 2 Oahu (M2O) race.
Paddling the iconic Starboard Unlimited 18’ x 26.75” and powered by his Lima Prepreg paddle, Tim became the first Canadian and oldest athlete to ever win this category. With support and insights from long-time teammate Connor Baxter, he turned 10 years of training and determination into one unforgettable crossing.
This is more than a win — it’s a story of perseverance, passion, and paddling beyond limits.
I am now a few days removed from what I can only describe as one of the most epic adventures of my SUP career. Since my first days on a Stand-Up Paddle board 10 years ago, Molokai to Oahu (M2O) has captivated my imagination. Arguably some of the worlds most gifted paddlers have crossed the Kaiwi Channel in search of M2O glory and I have been enthralled by the race, the Hawaiian culture and the challenge of the world’s biggest and most daunting conditions for paddling since the first day I learned of it. I made the final decision to try to attempt M2O after last year’s ICF world championships and decided to make it one of my big focuses for the 2025 season. As anyone who has done the race before knows, the logistical challenges of the event are insane so I am beyond grateful that my Starboard team mate, the G.O.A.T of M2O Connor Baxter was willing to help me understand what I needed to do and guide me through some of the process of equipment choices and executing the race.
My plan of attack for the months leading into the M2o was to accumulate as much volume as I could, and get comfortable on an unlimited board in the heaviest conditions I could find. I did this with help from Starboard, landing an ACE Unlimited from a few seasons prior for training on in Canada in order to get used to having a steering system and an 18ft long, wider board.
I arrived on Maui the week before M2O and I had planned on using both the classic Maliko run on the north shore, and the Molokai Holokai (M2M) as training and a warm up for the big show of M2O. I arrived in Maui Hawaii on July 16th and had one day to shake down my equipment; a Starboard Unlimited 18x 26.75 board and Lima Pre Preg paddle. I first did a Maliko down wind run on the 17th and then right to the M2M the next morning.
I felt quite confident in my Starboard gear for M2M because of the paddle the day before and came off the start line of M2M well, staying right in the front for the first few Km’s out into the Pailolo Channel. This Channel is known as one of the best Down Wind crossings there is and it did not disappoint with a steady east wind at about 17kts and some sizeable swell all moving in the right direction towards the finish line on Molokai. Unfortunately, my inexperience with the Channel became apparent about 20km or half way into the race where I found myself much too far north in the Channel, in between the Molokai coast line and the Kamalo buoy.
I had to adjust my course quite a bit to get out from shore but unfortunately the damage was done and despite getting some faster water and bumps, I had lost too much time to challenge for the win and settled for 2nd Place.
I took the next few days to acclimatize to the 6h time change and explore Maui with some cool hikes and amazing views while starting to wrap my head around the upcoming days and what it was going to take to be successful at M2O. I managed another 3 Maliko runs over the subsequent days and even managed a couple of Sup Surf sessions on west Maui in some mellow rolling waves. Each downwind run I completed on the Maliko was better than the next and by the time Friday rolled around (2 days before M2O) I felt somewhat prepared for the Kaiwi Channel.
Friday mid-day my best buddy Chris (my swimmer for the race) and I took the short flight from Maui over to Molokai and settled into our place on the west shore at the start line. Molokai for those who have not been there is a really special place with substantially less infrastructure then most of the other Hawaiian Islands.
Saturday, the day before M2O I paddled about an hour just trying to stay loose and turn on the aerobic system in preparation for the next day’s effort. It was already becoming evident that the race day conditions were going to be less than ideal, with models showing a North East and very mild wind. I tried not to focus on this too much as it was out of my control and instead tried my best to hydrate and eat in preparation. We also checked out the neighboring beach to the start area which was one of the nicest beaches I have ever seen
Finally race day came and it was go time! The day started with transporting all of our gear to my escort boat, followed by the Pule (Hawaiian Prayer). This was a special moment for me as I had seen this showing of solidary of all of the M2O athletes many times in pictures and could not believe I was about to actually do the race.
During a brief talk with my Captain Mark, we decided that because of the light wind conditions, a race line as straight as possible was the best strategy. We also settled on a nutrition plan that had my friend Chris jumping into the water and switching out my hydration and fuel every hour. Shortly after our pre-race disucssion, we lined up and started what was to become one of the most difficult events I have ever done. Most of the SUP field lined up to the far north of the start line hoping to benefit from the wind direction as early as possible however, Hayato Yamamoto from Japan and I both opted for clean open water and took the start line to the far south with the entire prone field in between us and the rest of the SUP’s.
My first few KM’s were fueled on adrenalin and very quickly both my Japanize competitor and I found ourselves at the front of the race. I also came to understand after only a few KM’s that we were going to be in for a very tough and long day. The wind conditions were very light and although there were a few bumps to be had, the unlimited boards seemed to really bog down in between the waves. The lack of wind also meant that the heat of the day was going to be a factor.
I started to focus on using as little energy as possible and sticking to my straight shot line while my competition took a much further north line and soon we were separated by about 500m but neck a neck. This scenario continued to play out for the first two hours of the crossing and by around the 20km mark all I could make out to the north was Hayato’s escort boat. My team continued to stick to the plan, our line and our nutrition strategy (120g of Carbs and 1.5 L of fluid per hour). I kept churning out the KM’s trying not to become demoralized on how slow each KM was and I continued searching for any bumps that would get the big unlimited surfing.
I had to survive some dark times as my body started to fatigue but I stayed positive and really tried to take in my surroundings by being present and absorbing the beauty of the channel. Slowly but surely Oahu started to become clearer on the horizon and I began to make out more details of slopes of Koko Crater and the opening of Hanauma Bay.
My team continued to assure me that our line was good and I eventually made my way to Koko Head and started to let myself believe that I may just pull off the win.
The one saving grace of the conditions on the day was that the notorious China Walls portion of the race, which usually challenges competitors with insane current, reverb and head wind, was relatively tame this time around, and I was able to put in a final push to the finish line at Maunalua Bay Beach park. The sensation of crossing the finish line having made it across the most famous channel in paddling can only be described as a dream come true for me. I am cognisant that the field in the SUP category has not recently been as stacked as it was in other years but I am very proud to be the first Canadian, and also the oldest competitor to ever win the Unlimited category at the M2O.
To be able to participate in the most iconic Stand Up Paddle race in the world and add my name to a trophy with names like Connor Baxter, Travis Grant, Dave Kalama, Kai Lenny and James Casey is truly unbelievable. To complete this epic adventure as a member of the Starboard team is the biggest honor of my paddling journey and much like the Tiki that is visual symbol of our brand I hope to continue to explore the world on the water.
