Wine and Kayaking at Chatham Vineyards

February 3, 2026

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.

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:

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.

How Did Chatham Vineyards and Winery Start?

Owned and operated by Jon Wehner and his wife, Mills, along with their three children, Chatham has been a working farm for over four centuries. A second-generation winegrower, Jon learned about the art of growing grapes from his parents who operated Great Falls Vineyard in Great Falls, Virginia for over thirty years.

Since 1999, more than twenty acres of high-density French vinifera varietals have been planted, including Merlot, Chardonnay, Cabernet Franc, Cabernet Sauvignon, and Petit Verdot. The winery was constructed in 2005 and currently produces between 3,000 to 5,000 cases annually.

The Wehner family’s commitment to sustainable viticulture and hands-on winemaking has resulted in consistently excellent wines that reflect the unique terroir of Virginia’s Eastern Shore.

The Rich History Behind Chatham

The land at Chatham Vineyards lies along Church Creek, which was patented back in 1640 and has been a working farm for over four centuries. Driving into Chatham winery, you’re taken down a long dirt road surrounded by gorgeous grape vines.

At the end of that road, you can’t help but notice a beautiful Federal-period brick house called Chatham that was built in 1818 by a man named Major Scarborough Pitts. It was named for William Pitt, the Earl of Chatham and friend of the American Revolution.

The property also contains historic outbuildings, barns, and two early 1900s homes on the property that have been recently renovated. One of the homes, a 1915 farmhouse, is a 3-bedroom, 2-bath rental available for guests. It would make the perfect retreat for a relaxing and romantic Eastern Shore getaway.

Exploring More of Virginia’s Eastern Shore

While you’re visiting Chatham Vineyards, consider extending your trip to explore more of this beautiful region. Virginia’s Eastern Shore is a hidden gem that offers:

Charming coastal towns: Visit Onancock for its historic district and waterfront dining, or explore Cape Charles with its beautiful beaches and Victorian architecture
Fresh seafood: The Eastern Shore is famous for its oysters, clams, and blue crabs. Don’t miss the opportunity to enjoy farm-to-table dining featuring local seafood and produce
Wildlife viewing: The area is part of the Virginia Coast Reserve, one of the last undeveloped coastal wilderness areas on the East Coast
Other wineries: Explore the Virginia wine country with additional stops at nearby vineyards

Planning Your Visit: What to Bring and Know

To make the most of your “Paddle Your Glass Off” experience, here are some tips:

Wear comfortable clothes that can get wet (quick-dry fabrics are best)
Bring sunscreen, a hat, and sunglasses
Water shoes or sandals with straps are recommended
Bring a reusable water bottle to stay hydrated
Don’t forget your camera or phone (in a waterproof case) for stunning photos
Consider bringing a small dry bag for personal items
Plan to arrive 15 minutes early for check-in and safety briefing

No prior kayaking experience is necessary. The SouthEast Expeditions guides provide instruction and ensure everyone feels comfortable before departing. The paddle is suitable for most fitness levels, as the pace is relaxed and there are opportunities to rest.

Why Virginia Wine Tourism Is Booming

Virginia’s wine industry has experienced remarkable growth over the past two decades. According to Virginia Wine, the industry now contributes over $1.37 billion annually to the state’s economy and attracts more than 2 million visitors each year.

The success of Virginia wineries can be attributed to several factors:

Ideal growing conditions in designated AVAs
Skilled winemakers, many trained at Virginia Tech’s renowned Enology-Viticulture program
Strong agritourism infrastructure
Proximity to major metropolitan areas like Washington, D.C. and Richmond
Innovative experiences like the kayak wine tour

Chatham Vineyards exemplifies this success, combining quality winemaking with unique visitor experiences that showcase the natural beauty of the region.

Making a Weekend of It

The “Paddle Your Glass Off” tour is the perfect centerpiece for a weekend getaway. Here’s a suggested itinerary:

Day 1: Arrive on the Eastern Shore, check into your accommodation in Cape Charles or Onancock. Explore the town, enjoy dinner at a local seafood restaurant.

Day 2: Morning kayak and wine tour at Chatham Vineyards. Afternoon relaxation at the beach or exploring local shops and galleries. Evening dinner featuring local cuisine.

Day 3: Visit additional attractions like the Eastern Shore of Virginia National Wildlife Refuge, Kiptopeke State Park, or explore more local wineries before heading home.

For accommodations, consider staying at the historic Chatham Vineyards farmhouse, charming bed and breakfasts in Onancock, or beachfront hotels in Cape Charles.

The Perfect Combination of Eco-Tourism and Wine Tourism

What makes the “Paddle Your Glass Off” tour so special is how it seamlessly blends eco-tourism with wine tourism. As you paddle through the pristine marshes and creeks, you’re exploring one of the most ecologically important areas on the East Coast.

The Virginia Coast Reserve, managed by The Nature Conservancy, protects 14 barrier islands and the surrounding waters. This undeveloped coastline provides critical habitat for migratory birds, sea turtles, and numerous fish species.

Your paddle takes you through this remarkable ecosystem, where you might spot osprey, great blue herons, egrets, and if you’re lucky, dolphins playing in the bay. This connection to nature enhances the wine tasting experience, as you gain a deeper appreciation for the land that produces these excellent wines.

If You Would Like to Skip the Adventure and Head Straight to the Wine Tasting

Chatham Vineyards welcomes visitors who prefer to arrive by car as well. The tasting room offers a relaxed, friendly atmosphere where you can sample their full range of wines.

Chatham Vineyards & Winery

chathamvineyards.com

Other Virginia Wine Experiences Worth Exploring

If you love the combination of outdoor adventure and wine tasting, Virginia offers several other unique experiences:

Bike and Wine Tours: Several regions offer guided bicycle tours through wine country
Hot Air Balloon Rides: Some vineyards offer balloon rides over the vineyards
Horseback Riding Tours: Combine trail riding with wine tasting in the Piedmont region
Wine and Chocolate Pairings: Many wineries offer special dessert wine and artisan chocolate events

For more Virginia travel inspiration, check out our guides to Chatham Vineyards, Chincoteague, and other day trips from Washington DC.

Why “Paddle Your Glass Off” Should Be on Your Bucket List

The “Paddle Your Glass Off” kayak and wine tour at Chatham Vineyards offers something truly special: a chance to slow down, connect with nature, and enjoy world-class wine in one unforgettable experience.

Whether you’re celebrating a special occasion, looking for a unique date idea, or simply want to try something different, this tour delivers. The combination of gentle exercise, stunning scenery, wildlife viewing, and excellent wine creates memories that last long after the last sip.

The tour has earned rave reviews on TripAdvisor, with visitors praising the knowledgeable guides, beautiful scenery, and high-quality wines. Many guests report that it was the highlight of their Eastern Shore visit.

As one recent reviewer noted: “This tour offers a little something for everyone. It’s the perfect blend of adventure, relaxation, and great wine. Our guide was fantastic, and the experience exceeded our expectations.”

Book Your Adventure Today

Ready to paddle your glass off? Don’t wait to book this popular tour. Spots fill up quickly, especially during peak season (May through October) and on weekends.

Visit SoutheastExpeditions.com or call (757) 210-8288 to reserve your spot. Chatham Vineyards and SouthEast Expeditions look forward to sharing this unique Virginia experience with you.

Whether you’re a wine enthusiast, an outdoor adventurer, or simply someone looking for a memorable way to spend a day on Virginia’s beautiful Eastern Shore, the “Paddle Your Glass Off” tour is an experience you won’t forget. Cheers to adventure!