Is previous kayaking experience required?

No, beginners are welcome. A safety briefing and basic instruction are provided before the trip.

What is the best time of year for this paddle and wine tasting?

Late spring through early fall offers the best weather and calm bay conditions.

Are rentals included or do I need my own kayak?

Kayak and all necessary gear are included as part of the guided tour.

How long is the entire experience?

The guided paddle plus vineyard visit typically lasts about 1.5 to 2 hours.

Can I bring children on the tour?

This trip is suitable for older children who can safely paddle and wear a life jacket.

Is transportation available from nearby towns?

Transportation is not provided; Franktown is the nearest town for accommodations or car access.

Paddle and Pour: Scenic Chesapeake Bay Adventure to Chatham Vineyards | Water Activities | Winery

Adventure Brief

Paddle across the tranquil Chesapeake Bay to Chatham Vineyards near Franktown, Virginia, where you’ll taste award-winning wines and unwind amid historic coastal beauty. This guided 45-minute kayak trip blends adventure with relaxation for a unique outdoor experience.

1.5–2 hours

easy

From $132.50

Located on Virginia's Eastern Shore near the quiet town of Franktown, Chatham Vineyards offers a unique outdoor experience that marries the calm beauty of the Chesapeake Bay with the rich flavors of award-winning wines. This adventure begins with a guided 45-minute paddle across the gentle bay waters, where paddlers glide past suede-colored marshlands, rustling seagrasses, and glimpses of waterbirds like ospreys and great blue herons. The salt-kissed breeze and wide blue sky set the stage for an intimate connection to this lesser-explored corner of Virginia's coastal landscape.

Upon arrival at Chatham Vineyards, visitors are greeted by a historic estate rich in agricultural tradition and an impressive lineup of grapes thriving in the sandy-loam terroir. The vineyard is renowned for its Church Creek Merlot, a full-bodied red that captures the character of this coastal terroir. Guests unwind with a thoughtfully curated cheese tray that complements the wine perfectly, offering a moment to taste and appreciate the fruits of the land and water.

This paddle-and-pour itinerary is designed for those seeking a blend of adventure with leisure, providing an accessible way to explore the area's natural and cultural heritage. The waters of Chesapeake Bay here are calm, making it suitable for beginners and nimble paddlers alike. The vineyard itself stands as a testament to sustainable farming practices and local craftsmanship, making it a standout destination for eco-conscious travelers.

The journey reveals much about the Chesapeake’s intricate estuary system while spotlighting Chatham Vineyards’ role as a key part of the region’s outdoor recreation scene. Whether you come for the paddle, the wine tasting, or both, this experience offers a refreshing break from traditional tourism routes, combining physical activity, scenic views, and culinary satisfaction in one elegant package.

Franktown serves as the nearby hub for visitors, with easy access from larger cities like Norfolk or Virginia Beach. The region’s low-key charm and natural amenities make it an excellent stopping point for travelers eager to experience Virginia's coastal outdoors paired with authentic local flavors. From kayaking quietly along the water to savoring the vineyards’ finest bottles, the Chatham Vineyards paddle adventure is a memorable way to engage the senses and enjoy an active day along Chesapeake Bay.

About SouthEast Expeditions

SouthEast Expeditions is a Virginia Eastern Shore outfitter specializing in guided paddling experiences, rentals, and coastal adventures. The company operates a range of kayak and stand-up paddleboard (SUP) tours — including sunset paddles from Cape Charles, family-friendly trips through Raccoon Creek, and extended explorations of barrier islands and Folly Creek marshes. Rentals include all-inclusive kayak and SUP packages with paddles and life jackets, plus bike rentals and beach setup services. Free delivery and pick-up for weekend or longer rentals adds convenience for visitors and locals. Guides on SouthEast Expeditions tours are described as experienced and safety-focused, offering route selection, local habitat interpretation, and beginner instruction. Trips emphasize wildlife viewing, hands-on aquaculture experiences like clamming and oyster education, and opportunities to support local conservation while exploring coastal marshes, creeks, and barrier beaches. Family-friendly options suit first-time paddlers and children, with gear provided and staff assistance available. Bookings can accommodate half-day and full-day itineraries, private groups, and mixed-activity days combining paddling, biking, and beach time. Emphasis on small groups and expert guidance helps minimize environmental impact and maximize comfort. Equipment maintenance and safety protocols are highlighted through routine checks and provided life jackets. As a local operator serving visitors to Cape Charles and the Eastern Shore, SouthEast Expeditions positions itself as a convenient, credible choice for outdoor experiences that combine natural history, active recreation, and easy logistics for families and adventurers alike. Advance online booking and flexible scheduling accommodate seasonal demand, group sizes, and rental delivery or pickup preferences easily and securely.