Windsurfing in Maui with Shawna Cropas
I started windsurfing about two months ago. Well technically, I started again. As a kid, I bought what must have been one of the OG windsurfers discounted mightily at a boat show, and tried my best on the St John river near Fredericton, New Brunswick. I had no idea what I was doing. The conditions were terrible. But I had a few moments of fun, and at least, the board was useful dragged behind my father's sailboat for practicing balance. In grad school, I again had the chance to windsurf. My MSc (and ABD PhD) was at Queen’s University in Kingston Ontario, but my supervisor, Dr Terry Shepard, was a world leader in software engineering process for real-time command and control systems at the Royal Military College, just across the bay on Lake Ontario. One of the perks of having connections at RMC was that they had a boathouse, with windsurfers, so in the summers I would rollerblade across the bridge and get out on the lake. Again, I had no idea what I was doing, but this time conditions were generally excellent.
Now back to the present. I’ve lived in the Bay Area for about six years, and figured that it’s quite a waste to not take advantage of the water. I've done some surfing at Bolinas and Pacifica, kayaked Tomales Bay and to Angel Island, and rented SUPs, but that's not the same as having a regular hobby on the water. Then I discovered the Cal Sailing Club in Berkeley this past winter. It’s an amazing volunteer run community at the public docks by the Berkeley pier. They have dinghies, keel boats, and dozens of windsurfers. Best of all, part of the trade off for low dues is that every member is required to do service hours at the club, so you have seasoned sailors and windsurfers offering their time to newbies like me.
I got out on the water for the first time mid May 2021. I was on a huge 205L board with a 4.3m sail. Wind was around 9-10 knots, I took the initial direction well, and was navigating around the sheltered cove like a pro. That got me my novice rating, meaning I could come back to the club on my own.
Cal Sailing’s rating system starts with Novice, allowing big boards and small sails, then after a Junior test on a 160L board and 5m sail you can start to take out slightly better boards and venture a bit farther out into the Bay. I wanted this. So my second time windsurfing I took a 160L board with the same 4.3m sail. I fell, a lot. The 160 board can hold my weight, but just barely, and you really have to get it to speed quickly after an uphaul to avoid sinking. From here I danced around a bit, tried a 180L board that was super easy and a lot of fun, started practicing with a 5m sail. Ultimately settled on a 160L board with 5m sail, that got me through quite a few sessions, including helping teach other novices--blind leading the blind, but in some ways I was perfect for teaching this level, the initial challenges so fresh to me.
This is about 4 weeks into my journey, I’m feeling pretty good about my progress in phase 1 of learning to windsurf. I’d also been watching a tonne of YouTube, especially the "Ride-along sessions with Cookie" series. But then I discovered Shawna Cropas. Her video on mast foot pressure was a revelation.
Shawna Cropas - Mastfoot Pressure from shawna cropas on Vimeo.
Despite feeling more comfortable, I was still on a big board, still ploughing through the water instead of planing, and the real fun of the sport doesn’t unlock until you can waterstart, use a harness and foot straps to really put more power into the board. And before any of that, I still had to get my position dialed. Even in relatively light winds I was being catapulted, or being pulled up into the wind. And I could not for the life of me sail downwind. I was good to get on the board, sail in a close reach, come about (sometimes successfully) close reach back. Repeat. With Shawna's mast foot pressure video, I saw a way through my current troubles, and also got the bug to set a goal of wave surfing in Maui in future.
Shawna is Canadian (like me), has lived all over the world, including stints as a pro windsurfer and world champion in the UK and Ireland. She now lives in Maui. I reached out to Shawna to explore options for next year. Figuring that I’d have the summer to figure out the harness and water starting. I wouldn’t be ready to wave surf by next year, but I’d be ready take my windsurfing to the next level, as a step in that journey. (The other step being that to wave surf you also need to be an expert surfer, because you’re combining windsurfing and sailing, with the added complexity of duck diving with a windsurf rig!).
This is when plans started to shift. Stef and I had flights booked back to Canada the first week of July, but as our departure date approached and the borders were still closed due to Covid, we started discussing options. With Maui fresh on my mind, it was a strong contender. After 18 months in quarantine, Maui would be different enough, and with being fully vaccinated the flight would be easy and safe.
I reached out to Shawna, a bit apprehensive about my level, but also happy to get started the right way--before I developed bad habits. We discussed options, and settled on three session times that worked for her. She hooked me up with a rental at Second Wind. It's an awesome shop, and rental gear was in excellent condition. By coincidence, the owner, Kevin Ozee is also Canadian.
Maui has some of the best surf beaches in the world. Ho'okipa is legendary. You see incredible displays of skill:
Thankfully, they also have Kanaha beach, with nice onshore trade winds that were 10-15 knots in the mornings. Beautiful sand, crystal clear water, nice stable strong winds. This is what it looked like the morning of my first lesson:
Lesson 1:
The first day we spent about 45 minutes on land, going over mast foot pressure, and correcting my bad tacking habits.
Let’s start with tacking: beginners are taught to hold the mast, and inch our feet around as we come about. As you get to bigger winds and smaller boards, this technique doesn’t work. Shawna would rather see me fall than establish the wrong muscle memory. The right way is to use the sail to bring the board into the wind, pushing through with your back foot to keep the board turning. Wrap your front foot all the way around the mast, and bring your front hand all the way forward on the boom. Then in one fluid controlled movement, dance your back foot to replace the front foot, bring your new backfoot back on the board, cross over your arm to grab the boom. Once in position, push the sail forward to come out of the wind and pick up speed. When executed properly, it’s like a dance with the sail.
Once on the water, we had a nice ~12 knot wind blowing across the beach. I could practice sailing out, coming about, and sailing back. We videotaped all sessions, so I could review later, and this was super helpful to see exactly why I wasn't getting the control I wanted. My big revelation in this first session was to keep the mast straight up. The tendency is to tip away from you, to make space on the board. But you really want it straight up. Probably sounds like amateur hour for those who know how to windsurf, but this had just not resonated until I heard it presented this way. You keep the nose of the board down through pressure from the wind on the mast, translated down to the mast foot. The mast needs to be straight up for this to work, and the sail powered up. I still wasn't getting the right position by end of Day 1, but I intellectually understood what I needed to do.
Lesson 2:
I spent some time after the first lesson reviewing footage, identifying that my mast was not nearly straight enough. This was a big culprit in constantly turning up into the wind, because with the sail leaned out like that I had no mast foot pressure (so nose of the board would creep up) and any wave would throw me off balance tipping the sail out and back. Shawna coached me through keeping the sail powered up and centered on the board, and this day I had my first real sensation of windsurfing. Not quite, but almost into a plane, I had my front foot pushed straight out ahead of me, hands back on the boom, power through the sail to the mast foot, and moving with speed and control. Huge progress.
With the basics out of the way, we moved on to the next big step in my progression, learning to use the harness. Even with proper form, sailing with your arms is a real workout. You can't sustain a long session like this, especially as the wind picks up. The windsurfing harness wraps around your waist, with a protruding hook that attaches onto straps on the boom. To get in, you sail up into the wind to take some power out of the sail, shift your pelvis up, in, and down to hook in, then lean back and let the harness take the sail. From here, your back hand needs only a light touch for balance, and your front hand for steering. You turn your hips forward, look to the direction of the wind, and sail away. Not going to lie, being hooked in is mildly terrifying. Especially as you get struck by gusts and need to react quickly to settle down into the harness to keep from catapulting. It's a sensation that I know will get easier in time, and also a reminder why it's so important to always be looking forward--so you can see the gusts before they strike. All in all, today was one of the best days I've ever had on a windsurfer. I got the sensation of standing properly on the board, crouched in heavy wind, standing up straight in light wind. Putting power through the sail to the mast foot, with mast straight up, keeping weight on the board back. And first experiences with the harness, that will take lots more practice but is setting me up for the really fun stuff to come.
Lesson 3:
Our goal for the third day was to wrap up learnings from the first two lessons, and to tackle beach starts. Unfortunately, the wind had different ideas. Whereas we had 12+ knots the first two days, wind on the third day was 6-8 knots. We thankfully had a bigger sail, but it still made practicing with the harness a challenge. The second issue was that the wind was almost directly onshore, making beach starts really tricky. Shawna worked through all this with ease, and while I didn't master the beach start, I have the mental model and was able to get up a couple of times albeit inelegantly.
The trick with a beach start is to grab the sail towards the top third of the mast, lift it out of the water, but low enough to not catch a lot of wind. Come under the sail, grab the boom, and rest the sail on your head. From here, you can push/pull the boom to turn the board. You want the board pointing straight out to sea. Then you come beside the board, in knee to waist length water. Now, place your backfoot on the board, pull it towards you and point slightly out of the wind. Immediately put the sail up with arms out straight, let it catch the wind, and pull you to stand your front foot on the board. Water starts follow a very similar technique, just need higher wind and/or a bigger sail. That will be my next project when I get home!
Summary:
I got back home this weekend and went back to Cal Sailing to try out my new skills. I still have a lot to learn, but was amazed at the progress. Before I left, I was taking out a 160L board with 5m sail; after nudged down to a 155L board with a larger 5.2m sail in similar 8-10 knot conditions. For these conditions, I really want to be on a 6m+ sail and an even smaller board, but this was progress nonetheless. More than the new gear, I was sailing with a lot more control. The big takeaways for others at a similar stage:
- Focus on mast foot pressure--get the mast vertical, use the power of the sail to drive down into the board. Don't let the sail tip out.
- Always look upwind--this turns your body and makes room for the sail. Especially important when you're in the harness, turn to face your belly button forward, watch for gusts,
- Build muscle memory for tacking properly--practice the dance on land, wrap your foot all the way around the mast, swap feet and hands in one smooth graceful motion.
- Have someone video you out on the water--it's invaluable to be able to see your position, identify what you were doing when you fell or lost power.
I feel very fortunate to have been able to learn from Shawna Cropas. She's an amazing instructor, and I look forward to following through on what I've learned, then hopefully getting back to Maui for next steps. If you're in the Bay Area and would like to go out windsurfing, would wholeheartedly recommend Cal Sailing, it's a great community that got me started. Hit me up, let's get out on the water!

