As the hub of Coastal Virginia, the city lies near major historical sites around the area.
If you find yourself asking, “How far is Chesapeake, VA from Williamsburg, VA?” then the answer may surprise you. Virginia’s Historic Triangle is only an hour north of Chesapeake.
Head 1.5 hours south to solve the mystery of Roanoke Island. Travel half an hour east to Virginia Beach and dip your toes in the Atlantic Ocean.
DAY 1-DAY TRIP TO ROANOKE ISLAND
Take a road trip with a southward jaunt to Roanoke Island. The first English explorers stepped ashore in 1584, only to vanish without a trace. You may think you’ve heard all the theories about the "Lost Colony" of Roanoke, but nothing compares to experiencing it firsthand.
Fort Raleigh National Historic Site protects and preserves the cultural heritage of the Native Americans, European Americans, and African Americans who have lived on Roanoke Island. Take in a performance of "The Lost Colony" – it’s the nation’s first and longest-running outdoor symphonic drama!
Roanoke Island Festival Park houses a replica 16th-century ship complete with costumed re-enactors.
DAY 2- HEAD TO VIRGINIA BEACH
Start your day at the First Landing Cross on the shores of Virginia Beach. The current granite cross was erected in 1935.
Fast forward almost 200 years with a visit to Old Cape Henry Lighthouse and Museum. Dating back to 1791, the first-ever lighthouse authorized by Congress is 191 steps to the top. It’s worth the climb for deep blue views of Cape Henry and Chesapeake Bay.
Head back into Chesapeake and tour the Great Bridge Battlefield & Waterways Museum – the site of the first American victory of the Revolutionary War. Then, treat yourself to an authentic savory wood-fired pizza at Andiamo Ristorante Pizza Napoletana.
DAY 3: EXPLORE VIRGINIA’S HISTORIC TRIANGLE
Immerse yourself in 17th-century life in Jamestown, Williamsburg, and Yorktown, the three settlements that makeup Virginia's Historic Triangle. Tour Jamestown settlement, where the first permanent English settlers arrived in 1607. Experience Colonial Williamsburg, where the ideas of independence and revolution took form.
Discover Yorktown, where the surrender of the British army prompted the end of the Revolutionary War and the beginning of a new nation. Yorktown Victory Center is an interpretive museum that showcases America's evolution from colonial status to nationhood.
Cap off your exploration at Passion the Restaurant. Creative, innovative cuisine sourced from local farmers and fishermen and a selection of 50 curated wines make for a celebratory end to a special day.
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Last Updated: 09/17/2020
