Never underestimate the underdog

The winning “Wannabe Pirates” aboard Seabiscuit post-race. L-R – Brittany (holding the team mascot, Rowan), Isaac, Ali, Mike, and Jason. Photo courtesy Ali Wisch

September 2021

By Ali Wisch

When I “entered” the 2021 Flip Flop Regatta, it was more like I invited myself to join my friend Isaac’s boat. Okay – that is, precisely, what it was. We’d sailed together a few times, bringing his Pearson 33, Seabiscuit, back and forth through the canal, as he kept it on a mooring outside of Boston for the summers. That is until he outsmarted all of us (liveaboards), bought a cheap powerboat to be his home base, and moved the sailboat to Boston permanently for more frequent sailing. I believe that the closer you are to your boat, the more likely you are to use it. You could, however, refer to Seabiscuit as a “storage unit” of sorts. For starters, we had to remove five batteries before the race painstakingly (if you’ve ever had to move a battery, I’m sure you would agree that painstaking might be an understatement). I’ve heard many liveaboard sailors dream of doing this, myself included (powerboat to live on, sailboat to sail), but Isaac did it. Not only did he follow through with this, but he also made an immediate effort to make use of this more convenient situation by entering Seabiscuit in a race, putting together a stellar crew, getting everything organized, and off we went.

I’ve always wanted to participate in Flip Flop because I have a soft spot for pursuit races, and there is a unique element of fun involved. Each team is encouraged to pick a “theme,” often wearing matching, sometimes outrageous costumes, some even decorating their boats to match. More importantly, it is for a good cause, and at a close second, Courageous Sailing Center, the regatta’s host, throws a bangin’ after-party.

As far as themes, there was a lot of creativity amongst the boats in the “Wannabe Pirates/Liveaboards” class (best name for a class, ever). Seeing as Isaac is from Kentucky and the boat’s name is Seabiscuit, we appropriately went with “derby.” So, picture big hats and fasteners, pink shorts and plaid shirts, Mint Julips (just kidding, that would have been great, though), plus an adorable necktie on Rowan, the Goldendoodle puppy who served as the team mascot, and at times our emotional support animal. After going around a stressful marker, there is nothing like petting a puppy.

And going around the markers was stressful. Getting to the start line was stressful. Let’s just say there was a high level of stress throughout the race. Between the five of us on board, our experience came down to me (if you count a couple of Wednesday night races and one regatta as “experience”) and another member of our crew, Jason, who was somehow able to teach the rest of us Racing 101, while we were racing. Given that, when we started to lose sight of other boats in our class, we were unsure of what exactly was happening. What we were one hundred percent sure of was that there was a fifty percent chance we might be winning and a fifty percent chance we were lost.

Maybe it was the matching costumes, perhaps it was the puppy, or maybe, to our surprise, we were good racers? Nobody knows for sure. But for a team that was almost certain, we would come in last, knowing that we were racing directly against friends who are seasoned racers and boats that were better equipped; at the end of the race, we discovered we had not been lost and had, in fact, won our class. I guess if you want to be a pirate bad enough…

When I reflect on the race, of course, I think about what we did tactically to help us get in the lead, but I spend more time remembering it as a beautiful day on the water and our crew’s enthusiasm. One of my biggest takeaways being that the dynamic between our crewmembers – everyone learning quickly and working hard to reach a common goal is what got us from start to finish – first. Whether you are in a race, on a delivery, or cruising with friends, you should all be all on the same page – even better if you get along. And if you must dress up in matching costumes for that to happen, I won’t judge you. I’ll applaud you.

For more about the Flip Flop, check out our Racing Pages, and please consider registering for next year. FMI: