5 days in Virginia Itinerary

5 days in Virginia Itinerary

Created using Inspirock Virginia tour itinerary planner

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Route & dates

5 days in Virginia Itinerary

Start: Hillsborough
Drive:  4​h
1
Williamsburg
— 2 nights
Drive:  1​h
2
Richmond
— 1 night
Drive:  2​h 30​min
3
Quicksburg
— 1 night
Drive:  4​h 30​min
End: Hillsborough

2
nights
Williamsburg

Williamsburg ©
Founded in 1632 as a fortified settlement on the high ground between two rivers, Williamsburg served as a colonial capital of Virginia for over 80 years.
Your day-by-day itinerary now includes Jamestown Settlement as well as Spooks and Legends Haunted Tours. Kick off your visit on the 30th (Thu): contemplate the long history of Jamestown Settlement and then join in the after-dark buzz at Spooks and Legends Haunted Tours. On the next day, steep yourself in history at Colonial Williamsburg and then explore the wealth of natural beauty at Colonial National Historic Park.

For maps, ratings, traveler tips, and tourist information, read our Williamsburg road trip tool .

Hillsborough to Williamsburg is an approximately 3.5-hour car ride. In May, daily temperatures in Williamsburg can reach 79°F, while at night they dip to 59°F. Finish up your sightseeing early on the 1st (Sat) so you can catch the train to Richmond.

Things to do in Williamsburg

Historic Sites Museums Nature
Find places to stay May 30 — Jun 1:
Highlights from your plan
Colonial Williamsburg ©
Colonial Williamsburg
Historic Jamestowne ©
Historic Jamestowne
Historic Jamestowne ©
Historic Jamestowne

1
night
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 2nd (Sun): brush up on your military savvy at White House of the Confederacy, stroll the grounds of Hollywood Cemetery, then get a sense of history and politics at Virginia Capitol Building, then get engrossed in the history at Virginia Holocaust Museum, and finally pause for some serene contemplation at St. John's Episcopal Church.

To find traveler tips, photos, other places to visit, and tourist information, you can read our Richmond trip itinerary site .

Traveling by train from Williamsburg to Richmond takes an hour. Alternatively, you can drive. In June, daytime highs in Richmond are 86°F, while nighttime lows are 66°F. Finish your sightseeing early on the 2nd (Sun) so you can travel to Quicksburg.

Things to do in Richmond

Museums Historic Sites
Find places to stay Jun 1 — 2:
Highlights from your plan
White House of the Confederacy ©
White House of the Confederacy
Hollywood Cemetery ©
Hollywood Cemetery
Virginia Holocaust Museum ©
Virginia Holocaust Museum

1
night
Quicksburg

Quicksburg ©
Start off your visit on the 3rd (Mon): learn about winemaking at Third Hill at DeMello Vineyards, examine the collection at Shenandoah Caverns - American Celebration on Parade, see the interesting displays at American Celebration on Parade, then explore the fascinating underground world of Shenandoah Caverns, and finally examine the collection at Main Street of Yesteryear.

To see more things to do, reviews, and more tourist information, use the Quicksburg trip itinerary site .

Traveling by car from Richmond to Quicksburg takes 2.5 hours. In June, daytime highs in Quicksburg are 83°F, while nighttime lows are 62°F. Wrap up your sightseeing on the 3rd (Mon) early enough to travel back home.

Things to do in Quicksburg

Museums Nature Parks

Side Trip

Shenandoah Caverns
Find places to stay Jun 2 — 3:
Highlights from your plan
American Celebration on Parade ©
American Celebration on Parade
Shenandoah Caverns ©
Shenandoah Caverns
Third Hill at DeMello Vineyards ©
Third Hill at DeMello Vineyards

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