17 days in Virginia Itinerary

17 days in Virginia Itinerary

Created using Inspirock Virginia trip planner

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Route & dates

17 days in Virginia Itinerary

Start: Orlando
Drive:  13​h
1
Virginia Beach
— 2 nights
Drive:  1​h 15​min
2
Williamsburg
— 4 nights
Drive:  2​h 45​min
3
Arlington
— 3 nights
Drive:  2​h 30​min
4
Charlottesville
— 3 nights
Drive:  2​h
5
Petersburg
— 3 nights
Drive:  10​h 15​min
End: Orlando

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.
Your day-by-day itinerary now includes Funny Bone. Step out of Virginia Beach with an excursion to Currituck Beach Lighthouse and Museum in Corolla--about 1h 05 min away. The adventure continues: take in the waterfront at Virginia Beach Boardwalk, explore the galleries of Virginia Aquarium & Marine Science Center, brush up on your knowledge of spirits at Chesapeake Bay Distillery, and see the interesting displays at Virginia Beach Surf & Rescue Museum.

For traveler tips, more things to do, maps, and more tourist information, read our Virginia Beach road trip tool .

Orlando to Virginia Beach is an approximately 4.5-hour combination of train, taxi, and flight. You can also drive; or do a combination of train and tram. Traveling from Orlando in May, expect Virginia Beach to be slightly colder, temps between 77°F and 60°F. Wrap up your sightseeing on the 19th (Tue) to allow time to drive to Williamsburg.

Things to do in Virginia Beach

Museums Parks Zoos & Aquariums

Side Trips

Currituck Beach Lighthouse and Museum, Chrysler Museum of Art
Highlights from your plan
Currituck Beach Lighthouse and Museum ©
Virginia Beach Boardwalk ©
Virginia Beach Boardwalk

4
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.
Colonial Williamsburg and St. Luke's Historic Church & Museum will appeal to history buffs. Plan for a day of cool, family-friendly fun on the 22nd (Fri) at Busch Gardens Williamsburg. The adventure continues: get engrossed in the history at Historic Jamestowne, pause for some serene contemplation at Bruton Parish Episcopal Church, steep yourself in history at Governor's Palace, and take a tour of Jamestown Settlement.

To see ratings, traveler tips, where to stay, and more tourist information, you can read our Williamsburg day trip tool .

Drive from Virginia Beach to Williamsburg in 1.5 hours. Alternatively, you can take a bus; or take a bus. In May, daytime highs in Williamsburg are 79°F, while nighttime lows are 59°F. Cap off your sightseeing on the 23rd (Sat) early enough to go by car to Arlington.

Things to do in Williamsburg

Historic Sites Museums Theme Parks

Side Trip

St. Luke's Historic Church & Museum
Highlights from your plan
Colonial Williamsburg ©
Colonial Williamsburg
Historic Jamestowne ©
Historic Jamestowne
Jamestown Settlement ©
Jamestown Settlement

3
nights
Arlington

Arlington ©
Located just across the Potomac River from Washington, D.C., the county of Arlington blends big city and sprawling suburban environments.
Get some historical perspective at Arlington National Cemetery and Old Town. Explore Arlington's surroundings by going to George Washington's Mount Vernon (in Mount Vernon), Manassas National Battlefield Park (in Manassas) and Steven F. Udvar-Hazy Center (in Chantilly). Next up on the itinerary: get to know the fascinating history of Tomb of the Unknowns, pause for some photo ops at Air Force Memorial, steep yourself in history at Arlington House - The Robert E. Lee Memorial, and make a trip to John F. Kennedy Grave Site.

To find traveler tips, other places to visit, maps, and tourist information, read our Arlington sightseeing planner .

Drive from Williamsburg to Arlington in 3 hours. Alternatively, you can do a combination of train and subway; or do a combination of bus, flight, and subway. May in Arlington sees daily highs of 76°F and lows of 58°F at night. Finish up your sightseeing early on the 26th (Tue) so you can go by car to Charlottesville.

Things to do in Arlington

Historic Sites Museums Neighborhoods

Side Trips

Mount Vernon, Manassas National Battlefield Park, Old Town, Steven F. Udvar-Hazy Center
Highlights from your plan
Tomb of the Unknowns ©
Tomb of the Unknowns
Arlington National Cemetery ©
Arlington National Cemetery
George Washington's Mount Vernon ©
George Washington's Mount Vernon

3
nights
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.
Thomas Jefferson's Monticello and Frontier Culture Museum will appeal to history buffs. Get out of town with these interesting Charlottesville side-trips: Luray Caverns (in Luray) and James Madison's Montpelier (in Montpelier Station). And it doesn't end there: steep yourself in history at James Monroe's Highland, contemplate in the serene atmosphere at Holy Comforter Roman Catholic Church, gain insight at The Glass Palette - Interactive Glass Art Studio, and stop by Michie Tavern ca. 1784.

For traveler tips, maps, ratings, and more tourist information, refer to the Charlottesville day trip tool .

Getting from Arlington to Charlottesville by car takes about 2.5 hours. Other options: do a combination of subway, bus, and flight; or do a combination of subway and train. In May in Charlottesville, expect temperatures between 76°F during the day and 55°F at night. Wrap up your sightseeing on the 29th (Fri) early enough to travel to Petersburg.

Things to do in Charlottesville

Historic Sites Parks Museums

Side Trips

Frontier Culture Museum, James Madison's Montpelier, Luray Caverns
Highlights from your plan
Thomas Jefferson's Monticello ©
Thomas Jefferson's Monticello
James Madison's Montpelier ©
James Madison's Montpelier
James Monroe's Highland ©
James Monroe's Highland

3
nights
Petersburg

Petersburg ©
Petersburg is an independent city in the U.S. Popular historic sites such as Pamplin Historical Park and Blandford Church and Cemetery are in your itinerary. Venture out of the city with trips to Charles City (Berkeley Plantation & Shirley Plantation) and Cold Harbor National Cemetery (in Mechanicsville). There's lots more to do: witness the site of a historic battle at Petersburg National Battlefield Park, contemplate the long history of Point of Rocks, and see the interesting displays at Pocahontas Island Black History Museum.

To find photos, reviews, other places to visit, and other tourist information, you can read our Petersburg trip builder site .

Traveling by car from Charlottesville to Petersburg takes 2 hours. In May in Petersburg, expect temperatures between 79°F during the day and 56°F at night. Finish up your sightseeing early on the 1st (Mon) so you can travel back home.

Things to do in Petersburg

Historic Sites Museums Parks

Side Trips

Charles City, Cold Harbor National Cemetery, Point of Rocks
Highlights from your plan
Pamplin Historical Park ©
Pamplin Historical Park
Petersburg National Battlefield Park ©
Berkeley Plantation ©
Berkeley Plantation

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