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A conversation with Jay Keeshan about the SYC's 2017 Vineyard Race

by David Schmidt, Sail-World USA Editor on 28 Aug 2017
The SYC’s 2017 Vineyard Race is set to unfurl on Friday, September 1 and will see over 100 boats competing for line and class honors. Rick Bannerot
As a sailing obsessed junior sailor growing up on Long Island Sound and sailing out of Stamford Yacht Club (SYC), where my parents are still members today, one of the surest signs of summer’s gradual slide into fall’s cooler temps and bright colors was talk of the annual SYC Vineyard Race, which unfurls annually over Labor Day weekend. And while I never liked the thought of exchanging my sailing gear for soccer cleats come autumn, I vividly remember seeing fleets of racing boats arriving at SYC from points abroad for the Vineyard Race, of course taking intense interest in the maxi yachts that would vie for line honors and-on a windy year-a new course record. Boats with names like Nirvana, Carrera, and Blue Yankee (the current record holder, with an elapsed time of 20 hours, 20 minutes and 15 seconds from the 2007 Vineyard Race), come to mind, as do plenty of other well-sailed and well-equipped yachts, both mighty and modest.

While there are a total of three courses (the Vineyard Race course, the Cornfield Point Course and the Seaflower Reef Course) available to entrants, the full-monty Vineyard Race course stretches for 238 nautical miles and starts just off of the SYC breakwater at Flashing Red Bell “32” (aka, “The Cows”) and takes the fleet down the length of Long Island Sound to the Buzzards Bay Light Tower, which must be left to starboard, then around Block Island, also leaving it to starboard, around The Cows (again, passing it to starboard), and then to the finish, leaving Nun “2” to starboard.

Before enjoying some well-earned libations, victuals and sleep at the finishing line, sailors must first negotiate Long Island Sound’s often fickle winds, big tides going through The Race or Plum Gut, the possibility of some brisk offshore conditions in Block Island Sound en route to the Buzzards Bay Light Tower, and (usually) choppy conditions east of Block Island, followed by the challenge of retracing your wake down Long Island Sound.

By all accounts, a good Vineyard Race (read: breeze-on conditions) ranks alongside some of the best coastal races that New England has to offer. (Strangely, given that my parents have been SYC members for more than a quarter century, and the fact that they have long owned and sailed a J/44, I’ve never actually sailed this race, making it one of the few Long Island Sound classics that is still on my long-term bucket list. Someday!)

This year’s Vineyard Race is set to unfurl on Friday, September 1, and will likely take most boats between one and three days to complete, conditions and vessels depending, of course. I caught up with Jay Keeshan, vice chairman for the 2017 Vineyard Race, via email, to learn more about this classic New England distance contest.

How is the competition level shaping up for the 2017 Vineyard Race? Also, what are participation numbers like compared to previous years?
We are looking great this year-we just passed the 100-boat mark, and we still have a couple weeks to go before the start. Last year at this time we had closer to 80 registered boats. So, we're happy to see that interest in the race continues to build.

Tactically, what do you see as the courses most challenging features (e.g., the Gut, Block Island, etc.)?
I think most would agree that the two crossings through the Race or the Gut are the race’s more distinctive features. Catching the currents in the right place at the right time is critical, and having experience can really make a difference.

Some sailors believe the Vineyard Race is actually five races: heading east down the Sound, then out into open ocean to round the tower and Block Island, the open-ocean leg from the Tower around Block Island, the leg across Block Island Sound, and then the journey back through the Gut and back down the Sound for the ride home. Each offer different conditions and completely different experiences.

Any advice for first-time Vineyard Race entrants?
Talk to as many experienced Buzzards as you can beforehand. Buzzards are sailors who have done at least 15 Vineyard Races, and you'll see them flying their Buzzard burgees at the start.

Also, I’d suggest spending plenty of time studying the tide and current charts.

Finally, be safe, have fun, and don't miss the awards party on Sunday!

Has the Vineyard Race always been open and welcoming to multi-hulls, or is this a newer evolution?
We've offered a multi-hull a class for almost ten years, but this year we have a particularly strong showing with the growth of the larger offshore catamarans and the Offshore Multihull Association.

Currently there are eight multi-hulls registered, and we plan to continue to build this class in coming years. It adds an exciting element to the race, and we think we'll be seeing more spectators out at the start, and more interest in the live tracking, which will be available through

What classes/divisions do you think will have the stiffest competition this year?
Due to the above-average participation, we are still determining the classes and class breakdowns, and we may still need to add an additional class or two. But there is always stiff competition within every class.

We are excited to see several of our recent Lightship Trophy winners including Christopher Dragon, Spookie, and Kenai all returning to the starting line this year.

What kinds of future steps do you think that events such as the Vineyard Race can take to lower their environmental footprint?
We are always conscious and respectful of the environment, and we are also always looking for ways to protect the beautiful waters we compete on. Our racing rules prohibit any waste overboard.

This year we'll be selling Vineyard Race reusable water bottles that can be re-filled to help cut down on the number of disposable bottles; hopefully that will catch on with the fleet!

There is also a major emphasis to reach out to participants through social media and electronic links rather than distributing paper. Competitors are encouraged to read the Sailing Instructions online and access the scratch sheets there as well.

Any thing else that you'd like to add, for the record?
Please stay tuned to us on Facebook and on our website at 2017 is promising to be an exciting year for the Vineyard Race.

If you can’t be here in person this year, give virtual racing a try through And if you’ve never done the race, please consider doing so as there’s always room for another boat at the start!

Protector - 660 x 82Zhik 2018 Yacht 728x90 2014