Waypoints and Wine

Vineyard hopping through Long Island Sound makes for a mellow shakedown cruise.

Issue 137: March/April 2021

It had been three years since we had last sailed through Long Island Sound. To be honest, it had been three years since we had sailed anywhere.

It wasn’t intentional, but as boat projects tend to go, one thing led to another. And another. And then we had a baby. Between feeding and caring for our daughter, Zoë, and working for a living, I was rewiring our interior while my husband, Jason, was rerigging our boat, among other projects. We were both doing everything we could to get us out of the slip.

Finally, after three years of endless boat projects we were ready to sail Chancelot, our Vagabond 42, again. And after three years, what we really needed more than the wind in our sails was a drink. With the warm August sun on our bow, we left our home port of New York City with a goal to explore Long Island’s wine region one anchorage at a time. As we headed up the East River dwarfed by the shadows of the New York City skyline, I could almost taste our first sip of rosé.

Sure, we could drive out to Long Island for a weekend and hit a few wineries, but why limit ourselves to two days when we could spend over a week sailing port to port, dinghying to shore and walking miles to truly earn each glass of wine we drank? Nautical winery-hopping seemed like the absolute best way to explore Long Island’s winemaking region and get in some great sailing while we were at it.

Long Island’s history in winemaking is relatively young, with the first vines planted in 1973. The region’s cool maritime climate makes it ideal for producing a variety of grapes. Cooling breezes from Long Island Sound and the Atlantic Ocean stave off extreme summer heat, while the surrounding waters also create a mild fall, allowing the fruit enough time to ripen. Despite its status as still just emerging, the region already boasts over 50 wineries and 38 tasting rooms, and we were determined to try as many of them as we could.

Though the majority of Long Island’s wineries are concentrated in the North Fork—eponymously named where the island’s main body splits into two 75 miles east of Manhattan—the wine trail actually starts much further west. Our first stop was Northport, located in the middle of Long Island and about 50 miles from the start of the North Fork.

Northport is a cute little town with a huge mooring field. We had been here before and so we knew to pick up a mooring ball from Seymour’s and to go ashore at the Northport Village dinghy dock. A dozen restaurants and boutiques line Main Street, and we headed straight to Copenhagen Bakery for an almond croissant and coffee to go. Before heading to Del Vino Vineyards, we stretched our legs with a walk through the lovely public park where Zoë tried to lure passersby to a game of imaginary chess on the concrete chess tables lining the park.

Though we could’ve easily walked the two miles from the dinghy dock to Del Vino (or biked if we’d had those onboard), we called an Uber just to keep things simple. We strapped Zoë into her travel car seat and settled in for a quick ride through residential streets. We could have opted to take a slightly longer route to enjoy the colonial and Victorian homes that line Woodbine Avenue, but we had our eyes on the prize.

Del Vino Vineyards is the first vineyard on the Long Island wine trail. It features 11 hedged vineyard acres producing five grape varieties including pinot noir, chardonnay, pinot grigio, sauvignon blanc, and riesling. The owners’ Italian heritage serves as inspiration for all parts of the winery, including the wine recipes and food menus. Perched on one of their picnic tables as Zoë played in the grass, we ordered a margarita pizza that was the perfect complement to the bold flavors of their Super Tuscan. All of our blood, sweat, and tears had paid off. I could literally taste our success as that first sip of wine hit my tongue.

The next morning, we motored 53 nautical miles east to Mattituck under a cloudy sky and wind on the nose. Mattituck is jokingly called the “Port of Last Resort” by many of our dock mates. The nickname refers to it being the only real place to safely tuck in on the Long Island Sound before you hit the more open waters of Block Island Sound.

But it’s far more than a quick place to drop the hook, and boaters who don’t make it far enough down the canal don’t get a chance to discover Mattituck’s true charms. We nerve-rackingly threaded our way through the first turns of the inlet, which are dredged to 11 feet but are incredibly narrow. The shoreline of the beaches on each side were only about 15 feet from the center of the channel.

Once we made it through the tight initial turns, the channel widened, and we enjoyed spotting the osprey nests tucked in the salt marsh and seeing all the wooden draggers tied up to small fishing docks. Tucked nearly two miles down Mattituck Inlet is a small anchorage with a dinghy dock, but we opted to stay dockside at Strong’s Water Club to hide out from some nasty weather that was headed our way.

We spent the next rainy morning chasing Zoë around the Long Island Aquarium, truly solidifying our need for a glass of wine (or two) later in the afternoon. The aquarium was quite impressive. It had seemingly endless exhibits, but the real winners for Zoë were the sharks and the touch tank. Jason and I loved the “Did You Know?” trivia posted throughout. Did you know, for instance, that a humpback whale calf consumes up to 99 gallons of milk a day? Neither did I!

In the afternoon, the skies dried up just long enough for us to make our way to Bridge Lane Winery, one of our favorite Long Island vineyards. We took a seat in the indoor tasting room as the sky was threatening rain at any minute. The bonus to the lousy weather was that we had the place all to ourselves, so Zoë was able to be a toddler and get into everything without bothering anyone.

We settled in with two tasting flights and a charcuterie plate. Bridge Lane’s vintners think of themselves as providing the wine for all occasions, so it comes in can, bottle, box, and keg form. While we didn’t take the leap with the keg (you better believe we measured multiple areas on board to see if it would fit though!), we did stock up on a few boxes of rosé. Every seasoned cruiser knows the benefits of boxed wine aboard, but it’s really nice to have good boxed wine for a change. We keep Bridge Lane’s rosé on tap aboard Chancelot all summer long.

A mile from Bridge Lane is Macari Vineyards. This beautiful winery offers indoor and outdoor settings with picturesque views of their vines. We headed to their tasting counter inside first, but quickly made our way out to their porch so that we could enjoy the vineyard views with our wine.

The next morning, we made a beeline for North Fork Doughnut Company. This place is a true indulgence. They offer spectacular renditions of classic yeast and cake flavors, as well as a rotating menu of special flavors. Zoë preferred a more traditional strawberry sprinkle, while I was a fan of the cereal killer.

North Fork Doughnut Company is half a block from the adorable Love Lane, and a third of a mile from the marina. Love Lane is the main street in Mattituck and only two blocks long. We browsed the handful of shops lining the street and then stopped at the eponymous Roanoke Vineyards on Love Lane. The tasting room offers both Roanoke Vineyard and Wolffer Estate wines, so we grabbed a bottle of Wolffer Summer in a Bottle and a table in their garden. Despite being in town, their garden was wrapped in vines, so we still felt like we were in our wine’s natural environment.

We had planned to go to Harbes Vineyard after Macari but lost track of time while sipping away, so we saved it for the next day. And, we were glad we did, because Harbes is an empire—a family farm, barnyard adventure, vineyard, and orchard. The vineyard is located in a 100-year-old potato barn and offers a beautiful indoor tasting experience, or you can opt to sit outside and do your tasting over a game of corn hole as we did. We then decided to indulge Zoë’s persistent request to check out the barnyard adventure, thinking we’d pet a few animals and be on our way. Instead we were greeted with a petting zoo, multiple playgrounds, a trampoline park, a playhouse town, and much more. Zoë was in heaven!

On our way out, we grabbed some fresh fruits and vegetables from the vineyard’s farm stand, lured by the spectacular colors of the produce. Before we hopped in our Uber back to the boat, we went across the street for a gorgeous bouquet of flowers from Pattie’s Berries and Bunches. One bouquet makes a few boat-sized bunches, and I loved how they brightened up every cabin on Chancelot.

The next morning, we enjoyed the pool and grounds at the marina before walking one-and-a-half miles of quiet back roads lined with beautiful homes to reach Shinn Estate Vineyards. When we arrived, we were somewhat blown away. The vineyard and tasting areas are truly gorgeous. Indoors there’s a cozy library, and outside are different tasting areas with views of the vineyard. There’s even a B&B that we would have loved to stay in had we not been visiting via sailboat. We tried two of their tasting flights al fresco. And, since we arrived when they opened, we had the place to ourselves, so no one was bothered by Zoë pouring water back and forth between cups or running through the grass.

Castello di Borghese Vineyard was probably our least favorite vineyard visit. It is located on a semi-main road, but unlike other vineyards, the tasting isn’t tucked in some secluded garden with sweeping views of the vineyards. It’s out in the open on cheesy blue plastic tables with views of the traffic flying by. On top of a subpar setting, none of the wines knocked us out, either. But, this place has great reviews, so perhaps we’re in the minority here.

After a few days of sipping our way through Mattituck, we left port and sailed toward Shelter Island to spend Labor Day Weekend. We sailed across the remainder of Long Island Sound, through Plum Gut, and around into the Peconic River. Plum Gut can get pretty spicy, so we timed the tide to transit during the slack. We passed through uneventfully, but the result was low tide, which meant we couldn’t get into Shelter Island comfortably with our 6-foot draft.

The wind was perfect, though, so we spent the next few hours enjoying sailing while we waited for the tide to come up. While sailing, we got a call from Safe Harbor Stirling in Greenport where we had wanted to go, but they initially had no slip for us because of the holiday weekend. The dockmaster offered to move his personal boat so that we could stay; how is that for service?

Greenport is a 20-minute drive, or a nearly 35-mile sail, from Mattituck if you head there directly. The marina offers a pool, on-site restaurant, and a free shuttle to town, which we gladly accepted.

The shuttle dropped us off about two blocks from the Greenport Tasting Room featuring One Woman Wines. Nuzzling up to the beautiful copper bar, we ordered our seventh tasting of the trip. We sat back to enjoy the live music with our wine while Zoë danced along. This winery is certified sustainable, which means they don’t use herbicides or harsh pesticides in their grape-growing.

Pleasantly buzzed, we walked through town and stopped in too many surf and clothing shops along the way so Jason could update his nautical t-shirt collection. Shopping and drinking is not the best combination for your budget, but his tiny boat closet was happy.

After a good night’s sleep, Jason threw on one of his new shirts and we headed for our next sipping stop. Located less than a mile’s walk from the marina, Kontokosta Winery is unique in that it sits atop sweeping bluffs with views of Long Island Sound. It was not lost on me that I had just sailed in these waters 17 nautical miles ago and it took me fewer than 20 minutes to walk here. As a sailor, I appreciate any opportunity to imbibe seaside.

It was a bonus that the libations were award-winning, hand-crafted wines. I ordered a glass of the Cabernet Franc, and Jason had the Anemometer Red Blend, then we headed towards the shore. With the wind blowing through our hair, we stared out to sea and dreamed of our next adventure.

A few hours later, with our boat sitting a few inches lower in the water from all the wine we were bringing back with us, and our hearts very full, Jason and I sat in the cockpit watching our daughter climb on the bimini frame, just happy as can be. The late summer sun was dreamily setting in the background, and I couldn’t help but think that this trip had been well worth the wait.

Good Old Boat Creative Director Kelley Gudahl lives aboard her Vagabond 42, Chancelot, in New York City with her husband, Jason, 3-year-old daughter, Zoë, and two dogs. You can read more about her adventures exploring the Long Island Sound and beyond at sailingchance.com.