Paddle Your Glass Off — A Chesapeake Bay Paddle to Chatham Vineyards

FRANKTOWN WATER ACTIVITIES FIELD GUIDE

Paddle Your Glass Off — A Chesapeake Bay Paddle to Chatham Vineyards

A guided outing that combines a 45-minute scenic paddle through Church Creek with a winery stop at Chatham Vineyards during a three-hour experience.

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Paddle Your Glass Off — A Chesapeake Bay Paddle to Chatham Vineyards.

Duration
Contact operator
Location
Franktown
Operator
SouthEast Expeditions
Category
Water Activities
Previously listed: USD 132.50

Adventure brief

Paddle Your Glass Off — A Chesapeake Bay Paddle to Chatham Vineyards

On the Chesapeake Bay, a short guided paddle threads Church Creek from the local Wharf of Bayford to the lawns of Chatham Vineyards, where the route pauses for an award-winning glass of Church Creek Merlot and a tour of the historic property before a return paddle.

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.

Route Schematic

Route Schematic

Key stops along the three-hour outing from launch to vineyard and back.

  1. Wharf of Bayford — Launch

    Meet at the local Wharf of Bayford and board boats provided by the operator to begin the guided paddle.

  2. Church Creek — Paddle

    A guided, scenic 45-minute paddle through Church Creek with interpretive notes on local wildlife and aquaculture.

  3. Chatham Vineyards — Tasting & Grounds

    Explore the historic property, enjoy a complementary wine tasting featuring Church Creek Merlot, and relax with a cheese tray; each pair of paddlers receives a complementary bottle.

  4. Return Paddle — Back to Wharf

    After time at the vineyard participants paddle back to the Wharf of Bayford to conclude the outing.

The full outing is scheduled as a three-hour experience; the operator provides all gear and welcomes first-time paddlers and children—participants should be prepared for a multi-hour on-water outing and follow guide instructions.

What the day feels like

What the Outing Feels Like

The trip unfolds as an easy, guided paddle: launch from the local wharf, glide through Church Creek while guides identify wildlife and aquaculture, step ashore for a winery experience and tasting at Chatham Vineyards with a cheese tray, then paddle back to the launch point—the whole outing organized to balance active time on the water with relaxed time at the vineyard.

A 45-minute Paddle through Church Creek

THE ROUTE

A 45-minute Paddle through Church Creek

The guided portion includes a roughly 45-minute paddle through Church Creek from the Wharf of Bayford to Chatham Vineyards, with guides pointing out local wildlife and aquaculture along the way.

Wine, Cheese and a Historic Vineyard Stop

THE TASTING

Wine, Cheese and a Historic Vineyard Stop

Once ashore at Chatham Vineyards participants enjoy a complementary wine tasting featuring award-winning Church Creek Merlot, time to sit outside with a cheese tray and a complementary bottle of Church Creek wine for every two paddlers.

Guides, Gear and a Boat Provided

THE INCLUSIONS

Guides, Gear and a Boat Provided

The operator provides the tour guide, all necessary gear and boat so first-time paddlers and kids can join with minimal personal equipment required.

Suitability

Who it's for

Who this outing suits best.

1
First-time PaddlersSpecifically suitable — the operator welcomes first-time paddlers and provides all necessary gear and instruction.
2
Families with KidsFamily friendly — children are welcome and the guided format and provided equipment make participation straightforward.
3
Casual Outdoor GroupsA relaxed, guided paddle that accommodates casual paddlers who want a short on-water experience combined with a vineyard stop.
4
Beginner PaddlersIdeal for beginners — the outing is designed to include novices with guide support and provided boats and gear.

Practical planner

Details to review before reserving

Timing & Duration

The full outing is organized as a three-hour experience, with a guided 45-minute paddle each way between the Wharf of Bayford and Chatham Vineyards.

What’s Provided

The operator supplies the tour guide, boat and all required gear; the winery experience and a complementary bottle of Church Creek wine for every two paddlers are included.

Money Matters

The price does not include gratuity.

Booking Notice

Review cancellation policies before reserving.

Frequently asked questions

Planning Your Outing

How long is the trip?

The outing is scheduled as a three-hour experience.

How long is the on-water paddle?

The guided paddle to Chatham Vineyards is about 45 minutes each way through Church Creek.

Is equipment provided?

Yes — the tour includes the boat and all necessary gear provided by the operator.

Is there wine included?

The winery experience and a complementary tasting are included, and every two paddlers receive a complementary bottle of Church Creek wine.

Can beginners and children participate?

Yes — first-time paddlers and kids are welcome on the outing.

How this guide was prepared

This field guide is synthesized using verified supplier specifications, route descriptions, and destination data. Some booking links may generate affiliate revenue for ADV Guides.

  • Verified: 2026-09-05T19:27:19.213Z

Some booking links may generate revenue for ADV Guides or The Adventure Collective.

Availability, pricing, schedules and operating details can change.

Trip details and contextual sources were reviewed by ADV Guides Editorial.

Paddle Your Glass Off — A Chesapeake Bay Paddle to Chatham Vineyards