The word adventure usually doesn’t come to mind when you think of wine tasting. You know how you usually just drive up to a winery in a car? So boring. What if you could kayak up to a winery while taking in some gorgeous views? Well, on Virginia’s beautiful and quaint Eastern Shore, you can.
What Is This Kayak and Wine Adventure All About?
“Paddle Your Glass Off” is a guided kayak and wine tour hosted by SouthEast Expeditions in partnership with Chatham Vineyards. You’ll spend a beautiful day paddling on the Chesapeake Bay and then stop along the way for a glass (or two) of award-winning Church Creek wine at Chatham Vineyards and Winery. How awesome does that sound?
The tour begins on the banks of Nassawadox Creek in the remote village of Bayford, VA. After a mini paddling lesson, you’ll journey south towards Church Creek, taking in the natural surrounding beauty, spotting Eastern Shore wildlife, and hearing interesting stories about the area’s rich history and ecology.

The tour begins on the banks of Nassawadox Creek in the remote village of Bayford, VA. After a mini paddling lesson, you’ll journey south towards Church Creek, taking in the natural surrounding beauty, spotting Eastern Shore wildlife, and hearing interesting stories about the area’s rich history and ecology.
Why This Tour Is Perfect for Wine and Outdoor Enthusiasts
This unique experience combines two of the best things Virginia’s Eastern Shore has to offer: outdoor adventure and world-class wine. Unlike traditional winery visits, the “Paddle Your Glass Off” tour immerses you in the natural beauty of the region before you even taste a drop of wine.
The Virginia Eastern Shore is designated as an American Viticultural Area (AVA), a wine appellation recognized for its unique growing conditions. The coastal climate, influenced by both the Atlantic Ocean and Chesapeake Bay, creates ideal conditions for growing French vinifera grapes.
According to the Virginia Wine Board, the state now boasts over 300 wineries, making it the fifth largest wine-producing state in the nation. But few offer the unique arrival experience of Chatham Vineyards.
What to Expect on Your Kayak Wine Tour
When you arrive on the shores of Chatham Vineyards, you’ll pull your kayak on land and then head over to Chatham’s tasting room for some delicious Church Creek wine and a behind-the-scenes tour of the facility.
After the wine tasting, you can relax for a bit at one of the tables overlooking the vineyard while enjoying your wine. Local cheese and bread plates are also available. After all that paddling, you deserve it!
The estate-grown wines you’ll taste include varieties like Chardonnay (both oaked and the popular unoaked “steel” chardonnay), Rosé, Cabernet Franc, Merlot, and their signature blends. Many of Chatham’s wines have won awards in regional and national competitions.
After you’ve finished your wine and perhaps purchased a bottle or two, you’ll get back in your kayak and paddle your way back to where you started your journey. The entire experience takes approximately 4 to 5 hours.
Tour Details and Booking Information
The tour is $89 per paddler, which includes the guide, boat, gear, and Chatham winery experience. Plus you get a complimentary bottle of wine for every two paddlers! First-time kayakers are welcome and encouraged.
Wine and kayak tours run daily from March through December, weather permitting. Advanced reservations through SouthEast Expeditions are required.
To book a “Paddle Your Glass Off” kayak and wine tour:
- Visit SoutheastExpeditions.com
- Call (757) 210-8288
- Email: Info@SouthEastExpeditions.com
SouthEast Expeditions has over 25 years of professional paddling experience, and their Virginia Certified Eco-Tour Guides are trained naturalists as well as world-class kayak instructors. The tour has been featured in The New York Times, Washington Post, Virginia Living, Southern Living, and Coastal Living.


