Thu, Jun 18: Fly into Norfolk, Virginia and transfer to the Mariners’ Museum and Park in nearby Newport News to kick off your tour.  Dedicated to the storied maritime heritage of the area, it is one of the largest such museums in North America. Explore world-class exhibits and fascinating stories that will inspire you to imagine your own adventure on the high seas! Later, check into the Marriott Newport News City Center, your home for the next four nights. Enjoy a Welcome Dinner and a delightful performance by The Liberty Dolls, a charming vocal trio who serenade audiences with World War II Andrews Sisters classic hits as well as tunes from past decades. (Meals: Dinner) 

Fri, Jun 19: This morning, take your reserved seat at Fort Monroe for the Sail250 Parade of Sail ceremony. Watch as the flotilla—stretching 12 miles across—cruises over the Chesapeake Bay Bridge-Tunnel and the Hampton Roads Bridge-Tunnel. Once the fleet reaches Hampton Roads, the ships will peel off to their respective host cities, including Norfolk, Portsmouth, Chesapeake, and Hampton. Take in the views of the ships still under sail as they proceed down the Elizabeth River to Norfolk. Enjoy a lunch buffet, before heading to Norfolk’s Town Point Park for the 50th Anniversary of Harborfest. Enjoy the traditional maritime attractions and tour some of the tall ships that just docked in the harbor from the parade this morning. Return to the hotel where the balance of evening is yours to enjoy as you wish. (B,L)

Sat, Jun 20: After breakfast this morning, visit the historic Jamestown Settlement, a living history museum recreating the first permanent English settlement in North America. Next, head to Williamsburg, founded in 1632 and named the capital of the Virginia colony in 1699. The town served as an important political center of Virginia until 1780. Explore historic Colonial Williamsburg, the world’s largest living history museum. Tour its key historic buildings, see the homes of some of the town’s most influential residents, watch live demonstrations of 18th century crafts, and enjoy lunch at one of the historic taverns. Return to the hotel following a fun-filled day. This evening, have the option to head to downtown Hampton for a “Summer Saturday” block party featuring free live music, and a variety of local food options for purchase. (B,L)

Sun, Jun 21: This morning transfer to Virginia Beach. A modern hotspot for summer vacationers and beachgoers, the city also contributes immense historical significance. Uncover the city’s rich history on a guided tour, making stops at many famous sites such as Cape Henry Lighthouse marking the first landing of the Jamestown settlers. Head to Virginia Beach Boardwalk for time on your own to shop, grab a bite to eat, and take in the beauty of the oceanfront. Next, tour the Thoroughgood House National Historic Landmark, one of the oldest surviving colonial homes in Virginia Beach, likely built in 1719 by Argall Thorowgood II, great-grandson of Adam Thorowgood who was a leader in the Virginia Colony. Learn about the impact this family had in region, get a glimpse into the daily lifestyle of colonists who lived there, and stroll through the English garden in full bloom. Afterward, head to Norfolk for an included dinner, followed by a serene sunset cruise. (B,D)

Mon, Jun 22: Enjoy a relaxed morning before checking out of the hotel and departing for the Norfolk Botanical Gardens. Take in the vibrant summer blooms on a guided trolley tour and included picnic lunch within the gardens. Afterwards, head to the airport for your evening flights home. (B,L)