Wine and kayaking at Chatham Vineyards


Usually the word adventure doesn’t come to mind when you think of wine tasting. Do you know how you usually drive to the winery in the car? very boring. What if you could kayak to a winery while enjoying some great scenery? Well, you can on Virginia’s beautiful and inviting East Coast.

So what is this kayak and booze adventure like?

“Paddle your glass away” is a guided kayak and wine tour hosted by a company called Southeast Expeditions in partnership with Chatham Vineyards. You’ll spend a beautiful day canoeing on the Chesapeake Bay and then stop along the way for a glass (or two) of award-winning Church Creek wines at Chatham Vineyards and Winery. How amazing does that sound?

Chatham Vineyard "Kayak your glass off" Wine tasting tour |

The tour begins on the banks of Nassawadox Creek in the remote village of Bayford, Virginia. After a small paddling lesson, you’ll travel south towards Church Creek to take in the surrounding natural beauty, spot the East Coast wildlife and hear some interesting stories about the area..

When you get to the beaches of Chatham Vineyards, you’ll haul your land-based kayak and then head to the Chatham Tasting Room for some delicious Church Creek wines and a behind-the-scenes tour of the facility.

Chatham Winery in Machipongo, Virginia |

After wine tasting, you can relax a bit at one of the tables overlooking the vineyard while enjoying your wine. Local cheese and bread dishes are also available. After all this blasphemy you deserve it. After you’ve finished with your wine, you’ll return to your kayak and paddle your way back to where you started your excursion.

The tour costs $89 per paddle which includes experience with the guide, boat, gear, and Chatham Winery. Plus you get a free bottle of wine for every two paddlers! First-time kayakers are welcome and encouraged.

Wine and kayak tours operate daily from March through December. Advanced bookings through Southeast Expeditions required. To book a “Paddle Your Glass Off” kayak and wine tour or to learn more, visit their website

Chatham Church Creek wine and cheese on Virginia's east coast |

How did the Chatham Vineyards and Winery get started?

Owned and operated by John Weiner and his wife, Mills, Chatham has been a working farm for more than four centuries. A second-generation viticulturist, John learned about the art of growing grapes from his parents, who ran the Great Falls Vineyard in Great Falls, Virginia, for over thirty years. Since 1999, more than twenty acres of French vinifera varieties including Merlot, Chardonnay, Cabernet Franc, Cabernet Sauvignon and Petit Verdot have been planted. The winery was established in 2005 and currently produces 3,000 to 5,000 cases annually.

Chatham Vineyards on Virginia's East Coast |

What is the history behind Chatham?

Land is located at Chatham Vineyards along Church Creek which was patented in 1640 and has been a working farm for over four centuries. On the drive to Chatham Winery, you are dropped off on a long dirt road surrounded by gorgeous vineyards. At the end of this road, you can’t help but notice a beautiful Federal period brick house called Chatham which was built in 1818 by a man named Major Scarborough Bates. It is named after William Pitt, Earl of Chatham and friend of the American Revolution. The property also has historic outbuildings, barns and two early 20th century homes on the property which has been recently renovated. One of the homes, a 1915 ranch house is a 3 bedrooms 2 Bathrooms are available for guests to rent. It would be the perfect getaway for a relaxing and romantic East Shore getaway.

Historic Chatham Vineyards Winery Chatham House |

If you want to skip the adventure and head straight for a wine tasting visit….

Chatham Vineyards and Winery
9232 Chatham Road, Machipongo, VA 23405
(757) 678-5588

Open daily 10am-5pm (April – December)
Closed on Tuesdays and Wednesdays (January – March)

Tasting fee: $5 per person


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