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Virginia Beach, Cape Charles & Norfolk

Sightsee your way through the beautiful villas and shoreline of Cape Charles on this picturesque tour. From there, move on to learn the history of Chesapeake Bay, visit an authentic oyster farm, and relax around one of the several wineries you will make a stop at during this getaway! Stroll around the botanical gardens of Virginia, and explore the aquarium and boardwalk of Virginia Beach. This tour is a true fusion of history, fun and relaxation, and delicious seafood cuisine! 


Day 1 - Depart for Virginia Beach, VA

This morning, we depart for a journey that takes us south to where the Chesapeake Bay meets the Atlantic Ocean – Virginia Beach, VA! Take in the beautiful views of the beach as we check into our oceanfront rooms, on the Boardwalk! Dinner is included this evening. (D)

Day 2 - Cape Charles, VA

After breakfast at the hotel, we depart for a  full day of sightseeing in Cape Charles. Geographically removed from the rest of Virginia, this narrow strip of land has a history and culture of its own. Picturesque villages dot the landscape between green pastures and farms, bordered on either side by the deep blues of the Chesapeake and the Atlantic. As we make our way out to Cape Charles by way of the Chesapeake Bay Bridge Tunnel, our guide will tell us about the history of Virginia Beach and the Eastern Shore, and teach us more about the bay and its significance to the region. Our first stop will take us on a VIP behind-the-scenes tour at a Virginia Oyster Farm, where we will see how Virginia clams and oysters are grown and harvested. From here, we will visit the Barrier Island Center, a museum that shelters yesterday’s culture of the islanders and waterman. After a stop at the Chesapeake Bay Blue Crab Company for lunch, we head to the Chatham Winery. This winery, constructed in 2005, was established on a working farm that has been at Chatham for four centuries. Today, the vineyards take up more than 20 acres of land. Tonight, after we’ve returned to Virginia Beach, dinner is included at Waterman’s Surfside Grille. (B, L, D)

Day 3 - Norfolk, VA

Breakfast is included this morning before our travels take us into Norfolk, VA. Don’t forget your camera as we will be visiting the beautiful Norfolk Botanical Gardens. The Gardens include 175 acres with 52 themed gardens, but there’s no need to worry about taking it all in because your ticket includes a tram tour. Each of the themed gardens allows you to see a variety of plants, from the cultivated to the wild. For lunch, we will head to the Mermaid Winery. They relate their vision to produce stunning wines to the mermaid, a mythical source of beauty, and that is where they found their name. This afternoon, we visit the Chrysler Museum of Art and the Moses Myers House. The Chrysler Museum of Art was brought to Norfolk, VA by Walter Chrysler Jr., the son of the car company founder. The city promised Chrysler support, space, and commitment, all of which prompted the move of the fledgling museum from a cramped Massachusetts church to Norfolk in 1971. The Moses Myers House was one of the first brick homes built in Norfolk following the Revolutionary War, which saw most of the town leveled. The home contains a remarkable number of furnishings original to the family, and is currently also home to a special exhibition within the home, Adeline’s Portal. Created by Wisconsin artist Beth Lipman, this exhibition reimagines and reinterprets items from the Myers household in clear glass, including objects like one of Adeline’s needlework samplers. Dinner this evening will be at the Norfolk Seafood Company.

Day 4 - Virginia Beach

Today we will head out after breakfast to the Thoroughgood House. Originally believed to have been built by Adam Thorowgood himself, one of Virginia’s first colonists, architectural historians of today agree that the house was built circa 1719 by Thorowgood’s son Argall, and completed by Argall’s wife Susannah. Some of the most famous elements, such as the extensive wainscoting and paneling, and the dramatic turned staircase, were added by Argall and Susannah’s son John. After, we return to Virginia Beach, the rest of the day is yours to spend however you choose: visit the aquarium, explore the boardwalk, or spend some time on the beach.

Day 5 - Depart Virginia Beach

We bid farewell to this beautiful seaside resort after breakfast. There are so many wonderful things to see and do here, we hope to see you back to enjoy all Virginia Beach has to offer! Evening arrival home.

Tour Details

Hotel / Lodging

The Oceanfront Inn

Oceanfront Inn

Virginia Beach


Roundtrip Motor-coach


8 Meals: 4 Breakfasts | 1 Lunch | 3 Dinners

Trip Highlights

Cape Charles
Oyster Farm Experience
Wine Tastings & Tours
Thoroughgood House
Chrysler Museum of Art
Norfolk Botanical Gardens
And More!

Upcoming Departures

Tour DatesAvailableDeparture Points Subject to Change
Mon May 23, 2022 - Fri May 27, 2022
5/23/2022 - 5/27/2022
  • Manchester, CT
  • West Hartford, CT
  • Danbury, CT
Mon September 12, 2022 - Fri September 16, 2022
9/12/2022 - 9/16/2022
  • West Springfield, MA
  • Wethersfield, CT
  • Milford, CT

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