From Seaside To Bayside: An Insiders Tour Of The Eastern Shore

Share in the secrets of this rural peninsula tucked between the broad waters of the Chesapeake Bay and the great Atlantic Ocean. The Eastern Shore specializes in “boutique tours.” Intimate tours allow your group to revel in scenic beauty and relax where island ponies run free. Discover hidden hamlets and a vital arts community exemplified by the Turner Sculpture and art gallery. “Drink in” the Eastern Shore at its wineries and taste the bay’s bounty with fresh-from-the tides seafood. Seaside to Bayside: “You’ll Love Our Nature.”

Day One:

Kayaking is easy for all ages and the perfect way to explore serene waters. Experienced eco-tour operators will take your group where only the dolphins and birds play. Meander through historic small towns, shop local art and antiques, lunch at a former 1920s men’s haberdashery in Cape Charles. Stay in lodges a gull’s cry from quiet beaches, fishing pier, bike and hiking trails.

Day Two:

Swing a club, raise a glass. Bay Creek Resort and Club boasts multi-award-winning golf courses: twin breathtaking Jack Nicklaus and Arnold Palmer courses along the Chesapeake Bay. Hit the happy wine trail. Three picturesque vineyards offer tastings: Bloxom WineryHolly Grove Vineyards and the county’s only kayak-winery tour at Chatham Vineyards.

Day Three:

Travel to the Colonial port of beautiful Onancock and explore its history. Then, ferry to Tangier Island, one of the last remaining working watermen’s hamlets on Chesapeake Bay. Or visit Wallops Island Visitors Center, one of NASA’s working launch facilities.

Day Four:

Go on Island Time! Share undeveloped beaches with the famed Chincoteague ponies at the Chincoteague National Wildlife Refuge. Climb the Assateague Lighthouse or bike the charming town. It’s a perfect way to work up an appetite for “fresh from the docks” seafood. Finish with a sweet “nightcap” at nostalgic ice cream parlors.


Visit a Virginia winery with your friends and family to discover exceptional, award-winning wines…