Long Island Wine Tour by Boat

wine tasting in Mattituck, New York
Enjoying a glass of Bridge Lane rose and views of the Mattituck Inlet.

It is no secret that Jason and I love wine. We look for wineries everywhere we go, so it is no surprise that we decided to find as many wineries close to each anchorage we stopped at along our sail through Long Island. You may not initially think of a Long Island wine tour by boat, but we had a lot of fun seeking them out and tasting as many wines as we could!

Please be sure to check each individual winery’s Covid-19 policies. Some of these wineries were visited before this pandemic began. This article required intense research over many visits that we happily did for you. You are welcome.

Northport Wineries

The first stop we made was Northport. Typically you think of the North Fork region as Long Island’s wine region, but there is no reason to wait until you sail all the way out on Long Island to begin sipping. We always pick up a mooring ball from Seymour’s when visiting Northport and tie up on the dinghy dock when we go to shore.

Del Vino Vineyards

Del Vino Vineyard is easily accessible from the Northport Village dinghy dock. At just over 2 miles away, you can easily bike there or call an Uber.

Del Vino Vineyards is the first vineyard on the Long Island wine trail. It features 11 hedged vineyard acres producing five grape varieties. Their sittings feature wine and light bites. A fun way to spend the afternoon.

Mattituck Wineries

Mattituck is jokingly referred to as 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 open water. The problem is, they never really give the location a chance, and don’t make it far enough down the canal to discover Mattituck’s true charms. Tucked nearly 2 miles down the Mattituck Inlet is a small anchorage with a dinghy dock or, if you prefer staying dockside, Strong’s Water Club. Both serve as a great spot for exploring some of Long Island’s best wineries.

Sailboats and powerboats anchored in Mattituck Inlet anchorage.
The anchorage at the base of the Mattituck Inlet can safely hold a handful of boats.

Roanoke Vineyards Wine Bar

The Roanoke Vineyards Tasting Room is located on the adorable Love Lane nestled between boutique shops and restaurants. At just a 1/3 of a mile from the dinghy dock, this is the easiest place to start your wine tour. The tasting room features both indoor and outdoor seating. This is not at a vineyard, so the outdoor seating is more garden seating but still very cute. They serve both Roanoke Vineyard wines and Wolffer Estate wines along with a small snack menu. Apparently, they even offer kid tastings of grape juice – how cute!

Bridge Lane Winery

Bridge Lane Winery is one of our favorite Long Island vineyards. They sell all of their wines in can, bottle, box and keg form. Yes, you can buy a keg of wine to fuel your entire summer sail. While we didn’t take the leap with the keg (you better believe we measured multiple spots to see if it would fit though!), we did stock up on a few boxes of rosé. Every cruiser knows the benefits of boxed wine aboard, but its really nice to have good boxed wine for a change. Their rosé is on tap aboard Chancelot all summer long.

Wine flights and charcuterie plate at Bridge Lane Winery during our Long Island Wine tour by boat
Enjoying the first three wines from our tasting at Bridge Lane Winery.

Bridge Lane Winery is located a mile from the dock which can easily be walked, biked or cabbed. It is located off a main road, so if you want to take back roads, it is 1.5 miles. They have a small tasting room and a lovely outdoor space with picnic tables for tastings. They have a small snack menu to accompany your tastings. They were very kid-friendly and welcomed our crazy toddler with open arms.

Macari Vineyards

A mile from Bridge Lane is Macari Vineyards. This beautiful winery offers indoor and outdoor tastings with picturesque views of their vines. To give you guys an idea how beautiful, the winery hosts a lot of weddings. They offer tastings paired with lunches from local restaurants and wines by the bottle or glass.

Grapes on the vineyards at Macari vineyards seen during our Long Island wine tour by boat.

Harbes Family Vineyard

Harbes is an empire. They have a family farm, barnyard adventure, vineyard and an orchard. I’m exhausted just typing that all out. The vineyard is located in a 100-year-old potato barn and offers a beautiful indoor tasting experience. Outside they have a ton of tables and outdoor yard games to keep the kids entertained while you’re sipping away.

bright orange tomatoes from harbes farm stand in Mattituck New York
The Harbes Farm stand in front of the vineyard offers amazing fresh produce.
Playhouses at Harbes barnyard adventure
If you have kids, be sure to stop by the family farm after your tasting. This place is amazing. So much for kids to do. I only wished they combined the vineyard with the farm. They have a petting zoo, climbing structures, games, a trampoline park and a ton of outdoor play houses.
gorgeous flowers from Patty's berries & Bunches in Mattituck, NY.
Be sure to grab a bouquet across the street at Patty’s Berries & Bunches before you leave. One bunch made about 5 boat-sized bunches.

Shinn Estate Vineyard

The classic tasting flight from Shinn during our Long Island wine tour by boat.
The Classic flight is one of three tasting flights they offer

Shinn is 1.5 miles from Strong’s Water Club, but its along back roads full of beautiful homes. The vineyard and tasting areas are truly gorgeous. Indoors they have a cozy library, but outside they have a ton of tasting areas with views of the vineyard. There is a lot of grass area for the littles to run around while you enjoy the tastings. They offer tastings, wine by the glass, bottles and a snack menu.

a man contemplating what to drink at shinn vineyards during our Long Island wine tour by boat.
We’ll take one of everything.

Borghese Vineyard

The classic wine tasting flight at Borghese Vineyard during our Long Island wine tour by boat.

Borghese was probably our least favorite tasting experience. It is located on a semi main road, but unlike other vineyards, the tasting experience isn’t tucked in some secluded garden with sweeping views of their vineyards. Its pretty out in the open on cheesy blue plastic tables. They offer 4 different tasting experiences, but none of the wines blew us away. This place has great reviews, so perhaps we’re in the minority here. Regardless, you should try for yourself during your wine tour!

Greenport Wineries

Kontokosta Winery

Kontokosta Winery is unique in that it sits atop sweeping bluffs with views of the Long Island Sound. As a sailor, I appreciate any opportunity to drink seaside. Add in the fact that the libations are award-winning hand crafted wines and I am in for a fine time. They offer wine tastings and a snack menu.

Kontokosta winery vineyards
photo via Kotokosta Winery

One Woman Wines Greenport

One Woman Wines is a certified sustainable winery which means they don’t use herbicides or harsh pesticides and are a full farm in addition to a vineyard. The owner, Claudia, grew up in Italy where she helped grow grapes on her family farm. She took that experience and has devotedly been tending to her vineyard on Long Island for nearly 20 years. You can sample her wines in the Greenport tasting room in town.

Cutchogue Harbor Wineries

Just a few miles up the road from Mattituck, but 38 nautical miles away (you have to sail around the North Fork), Cutchogue Harbor anchorage and its marinas provide access to 5 of the North Fork’s wineries in a 1-mile stretch. Sure we could just uber over there from Mattituck, but where is the fun in that? This is a Long Island wine tour BY BOAT after all. Sign us up! The start of this wine trail is a 2-mile trek from the harbor.

Puliese Vineyards

First up is Puliese Vineyards. They are a family-owned and inviting vineyard that produces wines with Cabernet Sauvignon, Chardonnay, Riesling, Merlot, Pinot Noir, Cabernet Franc, Pinot Grigio, Sangiovese, Gewurztraminer and Niagara grapes. However, if you are planning to visit multiple Long Island vineyards like we did, you have to try their sparkling wine flight.

Bedell Cellars

Bedell Cellars vineyards

Down the road 1/2 a mile from Puliese is Bedell Cellars. This is one of the more well-known wineries on the North Fork, and with reason. It is beautiful, and their wines are delicious. Their grounds host weddings and events as well as small tastings. They offer tastings, wines by the glass, bottles and small bites.

Pindar Vineyards

Pindar Vineyards is one of the oldest vineyards on Long Island as its founder helped create the wine making industry on Long Island in the 1980’s. Their vineyards are spread over 500 acres and produce 17 grape varieties! They offer tastings of their wines in their tasting room, but guests can bring their own food to picnic along with their wines.

Lenz Winery

The first grapes of the Lenz Winery were planted in 1978, making it one of Long Island’s oldest wineries. Today, guests can sample 4 different tasting selections along with a selection of meat and cheeses. Bonus points that the winery is dog friendly.


Raphael is an old school vineyard with its winery 12 feet below ground to help keep the wine cool in the summer and warmer during the winter. The vineyard offers wines by the glass and bottle to be enjoyed outside along with light snacks. They are not child or pet friendly, so keep that in mind if you are on the hunt for family-friendly spots.

Family enjoying our Long Island wine tour by boat.

So there you have it. Fourteen wineries for you to explore while you are anchored along the shores of Long Island. Are there any wineries that you love that we should check out?

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