8 days in Virginia Itinerary

8 days in Virginia Itinerary

Created using Inspirock Virginia planner

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Route & dates

8 days in Virginia Itinerary

Start: Chicago
Fly + Drive:  4​h 45​min
1
Lexington
— 1 night
Drive:  1​h 15​min
2
Charlottesville
— 1 night
Drive:  1​h 15​min
3
Richmond
— 2 nights
Drive:  3​h 45​min
4
Chincoteague Island
— 1 night
Drive:  2​h 30​min
5
Virginia Beach
— 2 nights
Fly:  4​h 30​min
End: Chicago

1
night
Lexington

Lexington ©
Home to two prestigious educational institutions, Lexington was founded in 1778.
Start off your visit on the 3rd (Mon): contemplate the long history of Lee Chapel and Museum and then take in the exciting artwork at Earth, Fire, & Spirit Pottery.

To see other places to visit, maps, where to stay, and other tourist information, use the Lexington trip website .

Chicago to Lexington is an approximately 5-hour combination of flight and car. You can also do a combination of flight and bus; or drive. The time zone difference when traveling from Chicago to Lexington is 1 hour. Traveling from Chicago in June, things will get a bit cooler in Lexington: highs are around 72°F and lows about 58°F. Finish your sightseeing early on the 4th (Tue) so you can drive to Charlottesville.

Things to do in Lexington

Historic Sites Wildlife Parks

Side Trip

Virginia Safari Park
Highlights from your plan
Lee Chapel and Museum ©
Lee Chapel and Museum
Virginia Safari Park ©
Virginia Safari Park
Washington and Lee University ©
Washington and Lee University

1
night
Charlottesville

Charlottesville ©
Situated at the foothills of the Blue Ridge Mountains, Charlottesville is perhaps best known as the home of three of the United States' founding fathers, including Thomas Jefferson.
Kick off your visit on the 5th (Wed): gain insight at University of Virginia, then do a tasting at King Family Vineyards, and then contemplate the long history of James Monroe's Highland.

For more things to do, other places to visit, traveler tips, and more tourist information, read our Charlottesville trip planner .

You can drive from Lexington to Charlottesville in 1.5 hours. Alternatively, you can do a combination of taxi and train. Plan for somewhat warmer temperatures traveling from Lexington in June, with highs in Charlottesville at 84°F and lows at 64°F. Wrap up your sightseeing on the 5th (Wed) early enough to drive to Richmond.

Things to do in Charlottesville

Shopping Wineries Historic Sites

Side Trip

King Family Vineyards
Highlights from your plan
James Monroe's Highland ©
James Monroe's Highland
King Family Vineyards ©
King Family Vineyards
University of Virginia ©
University of Virginia

2
nights
Richmond

Richmond ©
The capital city of Virginia, Richmond has diverse architecture, a large collection of monuments, and world-class museums that reveal the city's important role in American history.
Kick off your visit on the 6th (Thu): see the interesting displays at White House of the Confederacy, learn about all things military at Tredegar Iron Works, explore the different monuments and memorials at Hollywood Cemetery, then contemplate the long history of Virginia Capitol Building, and finally contemplate in the serene atmosphere at St. Paul's Episcopal Church. Get ready for a full day of sightseeing on the 7th (Fri): take in the history at Petersburg National Battlefield Park, steep yourself in history at Pamplin Historical Park, and then pause for some serene contemplation at St. John's Episcopal Church.

To find more things to do, reviews, other places to visit, and more tourist information, use the Richmond day trip planner .

Drive from Charlottesville to Richmond in 1.5 hours. Alternatively, you can take a bus. Expect a daytime high around 86°F in June, and nighttime lows around 66°F. Finish your sightseeing early on the 7th (Fri) to allow enough time to drive to Chincoteague Island.

Things to do in Richmond

Historic Sites Museums Parks

Side Trip

Petersburg
Highlights from your plan
White House of the Confederacy ©
White House of the Confederacy
Pamplin Historical Park ©
Pamplin Historical Park
Petersburg National Battlefield Park ©

1
night
Chincoteague Island

Famous for a wild breed of horses--Chincoteague Ponies--Chincoteague Island embraces the mystery of some of North America’s oldest inhabitants.
Kick off your visit on the 8th (Sat): surround yourself with nature on a nature and wildlife tour, get engrossed in the history at Museum of Chincoteague, and then grab your bike and head to Bike Depot.

For ratings, photos, more things to do, and other tourist information, use the Chincoteague Island trip planner .

You can drive from Richmond to Chincoteague Island in 4 hours. Other options are to take a bus; or take a bus. Expect a daytime high around 82°F in June, and nighttime lows around 66°F. Cap off your sightseeing on the 8th (Sat) early enough to go by car to Virginia Beach.

Things to do in Chincoteague Island

Outdoors Tours Wildlife
Highlights from your plan
Nature & Wildlife Tours
Museum of Chincoteague ©
Museum of Chincoteague

2
nights
Virginia Beach

Virginia Beach ©
Holding a record for the longest pleasure beach in the world, Virginia Beach showcases 35 miles of coastline and maintains a longstanding reputation as a family-friendly vacation destination.
Kick off your visit on the 9th (Sun): learn about all things military at Military Aviation Museum, enjoy the sand and surf at Sandbridge Beach, and then trot along with a tour on horseback. Here are some ideas for day two: examine the collection at Virginia Beach Surf & Rescue Museum, then get up close to creatures of the deep with a dolphin and whale watching tour, then make a trip to Cape Henry Lighthouse, and finally immerse yourself in nature at First Landing State Park.

For photos, more things to do, traveler tips, and tourist information, you can read our Virginia Beach trip itinerary planning app .

Drive from Chincoteague Island to Virginia Beach in 2.5 hours. Alternatively, you can take a bus; or take a bus. Expect a daytime high around 85°F in June, and nighttime lows around 69°F. Wrap up your sightseeing on the 10th (Mon) to allow time to travel back home.

Things to do in Virginia Beach

Outdoors Parks Wildlife
Highlights from your plan
Military Aviation Museum ©
Military Aviation Museum
Sandbridge Beach ©
Sandbridge Beach
First Landing State Park ©
First Landing State Park

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