Great Bridge Battlefield and Waterways Museum in Chesapeake
Exploring Nearby

Exploring Nearby

A great starting point for your next adventure

If you’re looking for things to do near Chesapeake, VA, consider a day trip! 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 and features living history sites the likes of Jamestown, Williamsburg, and Yorktown.

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. After working up your appetite exploring nearby sites, make your way back into Chesapeake for five-star dining right in the heart of it all.

Day 1: Day Trip to Roanoke Island

Take a road trip back in time with a southward jaunt to Roanoke Island. The first English explorers stepped ashore this mysterious island 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 the energy of the site 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 while you’re there – it’s the nation’s first and longest-running outdoor symphonic drama! Staged at the Waterside Theater, the show details the events of the 117 English settlers who vanished from Roanoke Island.

Roanoke Island Festival Park houses a replica 16th-century ship complete with costumed re-enactors that embody the bygone era. Once you’ve seen all the evidence firsthand, you’ll be ready to voice your own theory about the mysterious disappearance of the Lost Colony.

Day 2: Make Your Way to Virginia Beach

Start your day at the First Landing Cross on the shore of present-day Virginia Beach. The current granite cross was erected in 1935. But history reveals the first permanent English settlers originally laid claim to the site in 1607 for the glory of God, and of course the English crown.

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 well worth the climb for deep blue views of Cape Henry and Chesapeake Bay.

After spending the morning exploring Virginia Beach, head back into Chesapeake for a tour of the Great Bridge Battlefield & Waterways Museum – the site of the first American victory of the Revolutionary War.  Then, treat yourself to an authentic dinner of savory wood-fired pizza at Andiamo Ristorante Pizza Napoletana. You deserve it.

Day 3: Explore Virginia’s Historic Triangle

Immerse yourself in 17th-century life in Jamestown, Williamsburg, and Yorktown, the three settlements that make up 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. Explore a Continental Army encampment. Learn about Yorktown's importance as an 18th-century port. And witness the development of a new government with the Constitution and Bill of Rights.

Cap off your exploration of all there is to do in and around Chesapeake 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. Cheers to you!

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