When I was 15, some of my sailing classmates kicked off the summer by sailing the Figawi, New England’s legendary season-opening race held every Memorial Day weekend. A winding course between Hyannis and Nantucket, it was a seemingly epic voyage to a bunch of kids who had never sailed boats larger than 420s. My teammates, though, were quick to tell me that it was men-only. No girls allowed.
Yes, I know I should have found this suspicious and gotten a second opinion from someone who wasn’t a 15-year-old boy. But I was so embarrassed by the rejection that I never mentioned the Figawi to them again, and my hopes of sailing a “big boat” fell by the wayside. In fact, it was five years before it even occurred to me to look into it, and it would be another three years before I made it to the start line on a blazing Saturday morning this past May.
I set things in motion with a post on the 2016 Figawi crew message board asking if somebody would take me with them. By this point the race had turned into an item on my bucket list. Perhaps irrationally—because scores of women sail the race every year—I felt I had to confirm that yes, I could do it. That year, however, the Figawi came and went with no response to my post.
Several weeks later, I got an e-mail from a stranger saying he could use a hand for a race that weekend. I was interested, but I was also living in New York City at the time, and he was sailing on Buzzards Bay in Massachusetts. It took me a train, two buses and nine hours to get there, but I made it to the dock that Saturday morning, probably as terrified to meet a bunch of strangers off the internet as I was excited to sail.
My concerns were, of course, unfounded. The boat, a J/122 named Ursus Maritimus owned by Jim and Sam Masiero, is crewed by a welcoming crowd ranging in age from late teens to early 60s, and (I was excited to see) it included several women. One of them, Pia Peters, proudly introduced Sam as the only female driver in their fleet. I was star-struck.
After that, I continued to make the nine-hour trek for every race I could; though, as fate would have it, the small matter of my college graduation made it impossible to sail in the boat’s next Figawi, in 2017.
Finally, in 2018, it was my year. I certainly felt like it had been a long time coming as I hiked up the road with all my gear to the Hyannis Marina. I could’ve been walking into a fairground for all the excitement and the people buzzing about. There were so many boats jockeying for dock space that they had to be rafted together four-deep. I scanned the rigging for Ursus Maritimus’s battle flag—a white pawprint on a red background. Before I could find it, though, the crew found me. We were all easy to spot in our matching red shirts.
It was uncomfortably hot as we waited to dock out, passing around sunscreen and trying to stay hydrated. My teammates Garret and (another) Sam joined me as I explored the docks. Every kind of boat, from small day charters to high-performance thoroughbreds, like the polished TP52 Denali, shows up for this weekend, and we delighted in watching the elite sailors prepare their boats—something Jim considers a part of the race’s magic. “You can show up to crew on a boat, having never sailed before, and be up against teams that have pros,” he said. “What other sport lets you do that?” With nearly 200 boats and 3,000 sailors involved, the appeal is clear.
In terms of format, the Figawi is a pursuit regatta, meaning that start times are staggered based on each boat’s rating. The goal is to pass everyone who started ahead of you and to stay in front of everyone coming up from behind. First one to the finish wins. No waiting for corrected times afterward.
Being on a J/122, we had one of the later starts. However, due to some drama on board (we skied the jib halyard and Jim had to go up the mast to retrieve it) we made it to the line with little time to spare. Despite the heat onshore, we were graced with a perfect crisp breeze that held up throughout the race. When coupled with the cool spray, it ended up being a gorgeous day for a sail.
On the longer legs, we went an hour without a tack or sail change, so while Jim and our driver that day, Gary Deluc, were frowning at the boats around us and watching the chartplotter, the rest of us spent the afternoon on the rail, in serious contemplation of decidedly non-tactical questions like whether pineapple was an acceptable topping on pizza (an opinion that was held by a surprising majority on our boat).
Later a haze fell over the fleet making it difficult to see the competition, although the few boats that were close enough for us to see were too close for comfort. Luckily, visibility improved again as we approached the finish, which was just well as the last leg of the race was also the most crowded, with several divisions all converging at once.
Up to then, we’d managed to stay ahead of Denali and the Kerr 55 Irie 2. But the closer we got to the finish, the closer they got to us. We could only watch, more in amazement than disappointment, as Denali slipped by to leeward. In the end we finished in fifth out of the 11 boats in the S1 Division and, to our surprise and delight, one place ahead of Irie 2.
Though not the strongest finish we’ve had, this year was a special one Ursus Maritimus, as Jim and Sam have now sailed the race 20 times in the three boats they’ve owned over the years. Not surprisingly they have countless tales from their decades of sailing together, including every kind of worst-case weather scenario imaginable, some bad cases of seasickness and even an onboard marriage proposal.
They also have a flag from every Figawi they’ve competed in, and once at the dock, we flew them all. Many of the boats in the slips around us had similar displays, also proudly announcing how many years they’d been at it. In fact, pride in longevity is a constant throughout the fleet and the events of the weekend. At the awards ceremony, the emcee asked everyone who’d sailed five Figawis to put their hand up. Then 10. Then 20. Then 30. Admittedly, there were few hands still up at 30 years, but that there were any at all is a testament to the love that New Englanders have for this race; which all began in 1972 with a few competitive friends racing across Nantucket Sound. The group quickly grew, and by 1978, there was a formal race committee and three days devoted to the event. Flanked by several well-attended social events including the Figawi Ball, the race also began generating some serious income for the community. To date, the race organizers have been able to donate over $2 million to local charities and organizations in need.
Legend has it that the race’s name derives from an original competitor’s (heavily Boston-accented) question while sailing through the fog: “Where th’ figawi?” And the refrain was endlessly repeated throughout the weekend, both on various kinds of printed race merchandise and by the scores of inebriated sailors stumbling the island. Indeed, for many participants, the real event isn’t even the sail across the sound, but the party afterward and chance to get to know so many other sailors off the water. Jim and Sam, for instance, have friends who they only see once a year—on the dock in Nantucket—and as we walked about, they seemed to forever be running into an old friend.
Ultimately, Jim says the Figawi is more than just another race (or a deadline for him and Sam to get the boat ready for summer). It’s a bonding experience. “It’s like getting the family back together after they’ve been away all winter,” he says.
And while I can’t personally speak for every sailor out there, after spending the weekend sailing and exploring the island with the Ursus Maritimus crew, I felt closer to our team than ever.
Photos by Lydia Mullan