By Barbara “Basia” Karpinska

The Vineyard Race 2023, Doublehanded Division


PHRF DH division start, with Thin Man (USA 24) on the right   © Rick Bannerot/

And just like that summer has gone, and autumn arrived ushered by the Vineyard Race. Organized by Stamford Yacht Club, the Vineyard is an offshore racing classic dating back to 1932 and held annually over Labor Day weekend except for three years during World War II. The first race had 23 starters with five finishers. Fittingly, 89 boats participated in this year’s 89th edition.

Over the years the race evolved to a selection of three courses: the 238 nautical mile Vineyard Course, the 143 nm Seaflower Reef Course, and 116 nm Cornfield Point Course. The course selection depends on the size and rating of the boat. There are divisions for fully crewed and double-handed boats, non-spinnaker and spinnaker, ORC and PHRF rating.


The author at the helm   © Todd Aven


The original Vineyard Race Course can be a challenging collection of several races in one. Competitors must navigate eastward through Long Island Sound before passing into Block Island Sound through one of several narrow passages with tidal currents. After rounding the Buzzards Bay Entrance Light, they must leave Block Island to starboard before heading back into the Sound. A typical race involves a variety of conditions and requires several headsail changes.

Because this year’s weather forecast predicted light winds the full course, starting from Shippan Point in Stamford, CT to the light tower at the entrance to Buzzards Bay and back to the finish inside the Stamford Harbor breakwaters, was shortened to the Seaflower Reef Course.

Todd Aven and I are no strangers to the Vineyard Race and to each other. Both Corinthian sailors with careers in technology and healthcare, we first crossed paths racing on a mutual friend’s Farr 395. In 2007 Todd purchased a J/92 Thin Man and invited me to join his team. I became his regular bow and an occasional spinnaker trimmer for windward/leeward regattas. Our inaugural, fully crewed Vineyard Race together was in 2008, and we enjoyed several others over the years. Notably, Team Thin Man won the Cotton Blossom Performance Trophy in 2011, and achieved several podium finishes on all three courses.

In 2019, the mighty Thin Man transformed from a J/92 to a beautiful new J/99, named Sailing World ’s “Best Crossover Boat” in 2020. Because of the pandemic and a relocation, I have only been on the new Thin Man a couple times since, so I was thrilled when Todd asked me to co-skipper this year’s Vineyard Race.


Todd and Basia were awarded the Gillespie Memorial Trophy for the Best Performance by a mixed gender doublehanded boat.


This year’s race marked the fifteenth birthday of the Buzzards Society. Started in 2008 at Stamford YC, the Buzzards Society recognizes sailors who have participated in ten or more Vineyard Races. Having both been inducted a few years ago, Todd and I proudly flew our two Buzzard flags off the backstay.

To “get the rust off” we spoke a couple times before the race and agreed on the logistics. We provisioned for the full course the night before, so there was a guarantee there would be no food-related mutiny. Todd’s wife Catya made us delicious turkey meatballs, and a Brooklyn deli did not disappoint with chicken wraps. Because I eat more than anyone I have ever sailed with (and I have sailed with a lot of people!) I also made wraps (always good to have a backup). All this was supplemented by apples, nectarines, mandarins, carrots, an assortment of bars and, of course, jerky. We ate like kings without wasting any time on food prep during the race.

A big decision for this race is always the choice of the route through Long Island Sound. We attended Commanders’ Weather briefing the morning of the race to help validate our approach. The forecast called for wind shifting right into E or ESE by 1 to 2 pm, and consequently the first one or two hours on the nose, and then further right into SE-SSE later in the afternoon with best/strongest wind speeds closer to Connecticut shore, with lighter wind mid-sound and Long Island side. This confirmed our choice to stay closer to the Connecticut shore on the way out.

We competed against nine other boats in our division including another J/99, which inevitably felt like a match race within a fleet race. We started with a J1, and as the wind shifted, after two hours changed to a Code 0, which allowed us to get ahead of our “sister” 99. We kept a loose cover down the Sound, sailing relatively close to the rhumbline. The gift of shift kept on giving and by evening we changed headsails again, this time to the A2. The wind held at a solid 8 knots, we thought on the high end of the forecast. It was very shifty, 20-40 degrees range all afternoon, and although with the forecast in mind, we made the best of the breeze we were in, also observing the boats sailing closer to either the Connecticut or Long Island shore for any velocity and direction changes.

By 8 pm the wind was up to 10 knots from 220 degrees and kept building after the sunset to 11-12 knots with continued shifts. Although I could not fall asleep, I rested from 9 to 11 pm. We rounded at 12:45 am and started our return home. Todd was able to get some well-deserved rest from about 2 to 3:30 am. There was another change to the Code 0 before sunrise on the approach to the Long Sound Shoal to clear it, then we were each able to catch one more round of rest.

From 8 to 9 am the breeze built to 10-12 knots from 265-270 degrees, and we continued upwind in subsequently fluctuating wind velocity and sea state. We completed a couple directionally painful, yet necessary tacks. The best gift arrived in mid-afternoon Saturday. Shortly past Bridgeport, we experienced a persistent lift as high as 180-200 degrees that allowed us to get to the Cows Bell without tacking – Yay! By that point the wind was the highest we had seen, so we carefully considered one last sail change, and finished under the A3.

My fiancé Seth, accompanied by a bottle of adult bubbles, timed his arrival to Stamford Harbor perfectly and helped us deliver Thin Man to his home in City Island, NY.

As always, Stamford Yacht Club delivered a festive awards ceremony, with sponsors Team One Newport and BMW in attendance. We scored second in our division, fifth in PHRF overall (out of 45 boats), and were thrilled and humbled to be awarded the Gillespie Memorial Trophy for the Best Performance by a mixed gender doublehanded boat. ■

Tracks of a Thin Man: With light breeze in the forecast, year’s Vineyard Race was sailed on the 143 nm Seaflower Reef Course.



Growing up in Cracow, Poland, Barbara “Basia” Karpinska started sailing little boats on little lakes. She’s sailed on the tall ships Dar Mìodzieży and Fryderyk Chopin, and completed numerous offshore/ocean races in the US, Caribbean, Canada, UK, Ireland, Italy, and Slovenia including podium finishes. She has represented the USA and Poland in the World and the European Championships in the Mixed Offshore Doublehanded format in Beneteau Figaro3s.


Basia has racing experience in several one-design classes, and enjoyed frostbiting her Cook 11 at American Yacht Club. She relishes team racing for the New York Yacht Club, and is also a member of the Storm Trysail Club and the Buzzards Society. When not on the water, Basia is a healthtech and tech startup consultant, advisor, and an educator. She is a fellow and a member of the ACHE and the IWF, a mentor, a board member, and a motivational speaker. Occasionally she likes to sleep, and remains always grateful to Marine Weather University.