It’s a great feeling, as a coach, when members of the sailing team you have, in my case, the very great honor to coach, call you up and say, “Hey Coop, can we do these regattas?” I received such a signal last fall from Payton Canavan. Payton is one of two leaders of The Prout School Sailing Team and skipper of one of two pairs who are the school’s top four sailors. As is typical of her, she’d identified a couple regattas she thought would be fun to compete in, and done about half the legwork to get there.

From left to right on the Boardwalk at Captain’s Cove Seaport are Prout sailors Isabella DeSantis, Payton Canavan, Laura Borges and Avery Canavan. © Catherine Roche

Payton and the other three ladies (her younger sister Avery, Avery’s crew Laura Borges, and Payton’s crew Isabella DeSantis) have sailed together all season and had collectively taken a second in the Rebecca Herreshoff Trophy regatta in the spring. This New England Schools Sailing Association event is the only girls-only high school regatta in the Northeast (Yes, I’m still stunned by that fact too), sailed at Roger Williams with great assistance from their coach Amanda Callahan. Of a like mind in the idea of getting high school sailors out sailing, Amanda had proposed a fall regatta, and this was one Payton and her teammates wanted to do. It transpired that, being a new regatta, it didn’t quite get off the ground, a pity because it’s a great venue and Amanda runs a great facility and program. Oh well, next year.

The second regatta the girls had identified was the Catholic Cup, hosted by Captain’s Cove Seaport in Bridgeport, CT and organized by a fellow named Dave White, the Executive Director of Sail Black Rock. I have met Dave a couple times and we’ve corresponded, and I think he’s kind of a Connecticut version of me (I mean that in a nice way, Dave) in that an important tenet of his day is, “How can we get young people sailing?” Regrettably I could not be at the Catholic Cup because I was in Michigan, but thanks to Tech Score (and some texting) I was able to “watch them.”

I am very fortunate in the support Prout Sailing gets from the parents and two families in particular, Catherine Roche & Patrick Canavan, parents to Payton and Avery, and Isabella’s parents Angela & Chris DeSantis. They took on the driving, the lunches, helped with the organizing, and of course, cheered the team on. Prout took a combined second in the Catholic Cup, with Payton & Isabella finishing one point out of winning A fleet and Avery & Laura finishing third in B. The regatta was won by Fairfield Prep.

As you’ll read in commentary from three of the girls in this edition of Coop’s Corner, the venue is unique in that once sailors leave the dock, the rest of the day is administered on the water. Dave has a great group of folks at Sail Black Rock, one of whom provided a Grand Banks to serve as a mobile rotations dock. Whoever owned and loaned that very nice powerboat, many thanks mate.

One of my own basics for the sailors is that it’s their team and I give them as much authority to make decisions and make things happen as seems reasonable. With all Prout sailors in general and this four in particular, this is pretty wide leeway. I have never been disappointed. Applying this principle, I asked [WindCheck Publisher and Editor] Ben and Zep about having the girls write about the regatta, to which they eagerly agreed, and here we are. Thanks Ben and Zep, and nice job ladies.

Payton Canavan: The Prout Sailing Team competed at the Catholic Cup at Sail Black Rock last fall. The team, comprised of Payton Canavan (Class of 2019), Isabella DeSantis (‘20), Avery Canavan (‘21), and Laura Borges (‘20), managed to pull out a second place finish. We sailed in boats new to all four of us: square-headed FJs. Although we had no experience with these boats or the location of the racing, this did not hinder our ability to perform well as a team.

While the sail out to the racecourse was certainly long, I personally enjoyed the racing on Long Island Sound. Having grown up sailing in big wind since I began racing in Optis, I had a blast getting to sail in the heavier breeze once it filled. The course itself was pretty even as the day went on, which made it more challenging and fun. When Isabella and I had an issue with one of the pins coming out of our side-stay at the beginning of the day, the race committee lent us a spare ring-ding without hesitation and gave us extra time to make the necessary repairs, which helped ease the stress prior to racing. [Coop’s note: Dave remarked to me on the high level of seamanship Payton and Isabella showed in making this running repair.]

Isabella DeSantis: Prout Sailing is primarily a spring sport, but our coach, Joe Cooper, always tries to get us involved in the sailing world as much as possible. During the off-season, Coop helps us get involved in many sailing events, regattas, and “Kapers” to add to our resumés, and the Catholic Cup was an excellent opportunity for our team.

This was a well-run regatta with a very helpful staff, a beautiful venue, good competition, and a great group of high school sailors. The races were clearly marked, with square courses and a fair line. We had quite a few general recalls off the line, but overall the races were all great. The racing was a bit far from shore, but it provided better wind and pressure for the regatta.

Avery Canavan: I wanted to do the Catholic Cup because my teammates and I are always eager to start the sailing season early. We all have a lot of fun together and equally enjoy competing, so as soon as the idea to compete in this regatta came up, we were all on board.

The pre-race talk about rules and tactics by America’s Cup sailor David Dellenbaugh was very informative for young sailors such as myself. I found his outlook on stressing the importance of paying attention to every single factor of racing very interesting and helpful. The information I took away definitely helped me to really evaluate the choices I was making during a race, such as the perfect time to tack and deciding whether or not a choice would end up benefiting Laura and I throughout the race.

Payton Canavan: After racing, competitors were treated to Pepe’s Pizza and Regatta Ginger Beer before the awards. The awards for first, second, and third place were Mystic Knotworks rope bracelets in gold, silver and bronze, and we were lucky to receive silver ones after finishing second for the day. Overall, the racing and social aspects of the Catholic Cup made it a great regatta to compete in.

The Crusaders rock their second place prizes, silver rope bracelets from Mystic Knotworks. © Catherine Roche

I thoroughly enjoyed the friendly camaraderie with the other sailors during the on-the-water rotation. We had a chance to meet sailors from other schools, forming many fast friendships. Having fellow competitors within the same radius gave us the opportunity to talk and get to know each other instead of just retreating to our teammates and coaches, which is what can happen when rotations are on land. This allowed for sailors to interact with one another in a fun and competitive manner, which is what sailing is all about!

Australian born, Joe ‘Coop’ Cooper stayed in the U.S. after the 1980 America’s Cup where he was the boat captain and sailed as Grinder/Sewer-man on Australia. His whole career has focused on sailing, especially the short-handed aspects of it. He lives in Middletown, RI where he coaches, consults and writes on his blog,, when not paying attention to his wife, college senior son, dog and several, mainly small, boats.