31 days in Virginia Itinerary

31 days in Virginia Itinerary

Created using Inspirock Virginia travel route planner

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Route & dates

31 days in Virginia Itinerary

Start: Washington DC
Drive:  30​min
1
Arlington
— 3 nights
Drive:  1​h 30​min
2
Winchester
— 2 nights
Drive:  2​h
3
Shenandoah National Park
— 4 nights
Drive:  1​h 45​min
4
Lexington
— 3 nights
Drive:  1​h 15​min
5
Charlottesville
— 4 nights
Drive:  2​h 15​min
6
Williamsburg
— 5 nights
Drive:  1​h 15​min
7
Virginia Beach
— 4 nights
Drive:  2​h 30​min
8
Chincoteague Island
— 5 nights
Drive:  3​h 45​min
End: Washington DC

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 out of town with these interesting Arlington side-trips: National Museum of the Marine Corps (in Triangle), George Washington's Mount Vernon (in Mount Vernon) and Steven F. Udvar-Hazy Center (in Chantilly). There's lots more to do: stroll the grounds of Arlington National Cemetery, appreciate the extensive heritage of The Tomb of the Unknown Soldier, have some family-friendly fun at iFLY Indoor Skydiving - Loudoun, and take in the history at Manassas National Battlefield Park.

For traveler tips, where to stay, and tourist information, use the Arlington attractions planner .

Washington DC to Arlington is an approximately half hour car ride. In August, plan for daily highs up to 87°F, and evening lows to 71°F. Finish your sightseeing early on the 4th (Sun) to allow enough time to drive to Winchester.

Things to do in Arlington

Historic Sites Parks Museums

Side Trips

National Museum of the Marine Corps, iFLY Indoor Skydiving - Loudoun, Old Town, Manassas National Battlefield Park, Steven F. Udvar-Hazy Center
Highlights from your plan
The Tomb of the Unknown Soldier ©
The Tomb of the Unknown Soldier
Arlington National Cemetery ©
Arlington National Cemetery
Steven F. Udvar-Hazy Center ©
Steven F. Udvar-Hazy Center

2
nights
Winchester

Winchester ©
Winchester is an independent city located in the northwestern portion of the Commonwealth of Virginia. Kick off your visit on the 5th (Mon): admire the sheer force of Cascade Falls, examine the collection at Shenandoah Valley Civil War Museum, then get a taste of life in the country at Rocking S Ranch, and finally get advice or help at Handley Regional Library. Keep things going the next day: get engrossed in the history at Stonewall Jackson's Headquarters, then explore the world behind art at Museum of the Shenandoah Valley, and then trek along Buzzard Rock North.

To see ratings, maps, more things to do, and other tourist information, read Winchester trip builder tool .

Drive from Arlington to Winchester in 1.5 hours. Alternatively, you can take a bus; or take a train. Traveling from Arlington in August, things will get little chillier in Winchester: highs are around 82°F and lows about 62°F. Finish up your sightseeing early on the 6th (Tue) so you can go by car to Shenandoah National Park.

Things to do in Winchester

Parks Museums Trails

Side Trips

Buzzard Rock North, Cascade Falls
Highlights from your plan
Rocking S Ranch ©
Rocking S Ranch
Cascade Falls ©
Cascade Falls
Stonewall Jackson's Headquarters ©
Stonewall Jackson's Headquarters

4
nights
Shenandoah National Park

Shenandoah National Park ©
Shenandoah National Park showcases a particularly scenic section of Virginia's Blue Ridge Mountains.
Appalachian Trail has been added to your itinerary. Change things up with these side-trips from Shenandoah National Park: Cooter's in the Country (in Sperryville) and Luray Caverns (in Luray). There's lots more to do: cruise along Skyline Drive, look for all kinds of wild species at Elkwallow Picnic Area, hike along Mary's Rock Summit Trail, and tour the pleasant surroundings at Old Rag Mountain Hike.

For reviews, other places to visit, maps, and other tourist information, you can read our Shenandoah National Park vacation website .

Getting from Winchester to Shenandoah National Park by car takes about 2 hours. Other options: do a combination of bus and taxi; or do a combination of bus and flight. In August in Shenandoah National Park, expect temperatures between 84°F during the day and 65°F at night. Wrap up your sightseeing on the 10th (Sat) to allow time to drive to Lexington.

Things to do in Shenandoah National Park

Parks Nature Outdoors

Side Trips

SoLace Studios Fine Handcrafts, Luray Caverns, Cooter's in the Country
Highlights from your plan
Appalachian Trail ©
Appalachian Trail
Luray Caverns ©
Luray Caverns
Skyline Drive ©
Skyline Drive

3
nights
Lexington

Lexington ©
Home to two prestigious educational institutions, Lexington was founded in 1778.
Venture out of the city with trips to Cass Scenic Railroad State Park (in Cass), National D-Day Memorial (in Bedford) and Green Bank Observatory (in Green Bank). The adventure continues: gain insight at Virginia Military Institute, learn about all things military at Museum of Military Memorabilia, steep yourself in history at Lee Chapel and Museum, and pause for some photo ops at Stonewall Jackson Memorial Cemetery.

To find traveler tips, other places to visit, and tourist information, go to the Lexington trip tool .

Traveling by car from Shenandoah National Park to Lexington takes 2 hours. Alternatively, you can do a combination of taxi and bus. In August, Lexington is slightly colder than Shenandoah National Park - with highs of 71°F and lows of 57°F. Finish your sightseeing early on the 13th (Tue) so you can drive to Charlottesville.

Things to do in Lexington

Parks Museums Wildlife

Side Trips

Natural Bridge, Green Bank Observatory, National D-Day Memorial, Cass Scenic Railroad State Park
Highlights from your plan
National D-Day Memorial ©
National D-Day Memorial
Virginia Military Institute ©
Virginia Military Institute
Virginia Safari Park ©
Virginia Safari Park

4
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.
Explore Charlottesville's surroundings by going to St. Thomas Parish Church (in Orange), James Madison's Montpelier (in Montpelier Station) and Luray (The Car and Carriage Caravan Museum & Stony Man Mountain Hike). Next up on the itinerary: admire the natural beauty at Monticello, relax in the rural setting at Carter Mountain Orchard, admire all the interesting features of Appomattox Court House National Historical Park, and contemplate the long history of James Monroe's Highland.

To find more things to do, where to stay, and tourist information, refer to the Charlottesville travel route builder .

You can drive from Lexington to Charlottesville in 1.5 hours. Another option is to do a combination of taxi and train. Plan for a bit warmer temperatures traveling from Lexington in August, with highs in Charlottesville at 84°F and lows at 65°F. Finish up your sightseeing early on the 17th (Sat) so you can go by car to Williamsburg.

Things to do in Charlottesville

Historic Sites Parks Museums

Side Trips

Luray, Appomattox Court House National Historical Park, Frontier Culture Museum, St. Thomas Parish Church, James Madison's Montpelier
Highlights from your plan
Monticello ©
Monticello
Stony Man Mountain Overlook ©
Stony Man Mountain Overlook
Carter Mountain Orchard ©
Carter Mountain Orchard

5
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.
Get out of town with these interesting Williamsburg side-trips: Virginia Museum of Fine Arts (in Richmond), Smithfield (Isle of Wight County Museum & St. Luke's Historic Church & Museum) and Newport News (The Mariners' Museum & Park & USS Monitor Center). Next up on the itinerary: cool off at Busch Gardens Williamsburg, take in the exciting artwork at Williamsburg Art Gallery, pause for some serene contemplation at Bruton Parish Episcopal Church, and stop by Quirks of Art.

To find where to stay, other places to visit, traveler tips, and more tourist information, you can read our Williamsburg trip planner .

Getting from Charlottesville to Williamsburg by car takes about 2.5 hours. Other options: take a bus. In August, plan for daily highs up to 89°F, and evening lows to 70°F. Wrap up your sightseeing on the 22nd (Thu) early enough to drive to Virginia Beach.

Things to do in Williamsburg

Museums Historic Sites Theme Parks

Side Trips

Smithfield, Newport News, Virginia Museum of Fine Arts
Highlights from your plan
Busch Gardens Williamsburg ©
Busch Gardens Williamsburg
Colonial Williamsburg ©
Colonial Williamsburg
Historic Jamestowne ©
Historic Jamestowne

4
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.
Get out of town with these interesting Virginia Beach side-trips: Cape Charles (Stage Door Gallery, Cape Charles Beach, & more). The adventure continues: take in the waterfront at Virginia Beach Boardwalk, enjoy the sand and surf at Virginia Beach, brush up on your military savvy at Military Aviation Museum, and step aboard Battleship Wisconsin.

To find ratings, maps, reviews, and more tourist information, read our Virginia Beach sightseeing site .

Traveling by car from Williamsburg to Virginia Beach takes 1.5 hours. Alternatively, you can take a bus; or take a bus. In August, daily temperatures in Virginia Beach can reach 86°F, while at night they dip to 72°F. Wrap up your sightseeing on the 26th (Mon) to allow time to drive to Chincoteague Island.

Things to do in Virginia Beach

Parks Beaches Outdoors

Side Trips

Norfolk, Cape Charles
Highlights from your plan
Virginia Beach ©
Virginia Beach
Virginia Beach Boardwalk ©
Virginia Beach Boardwalk
Military Aviation Museum ©
Military Aviation Museum

5
nights
Chincoteague Island

Famous for a wild breed of horses--Chincoteague Ponies--Chincoteague Island embraces the mystery of some of North America’s oldest inhabitants.
Chincoteague Island is known for nature, wildlife, museums, shopping, and historic sites. Your plan includes some of its best attractions: look for all kinds of wild species at Chincoteague National Wildlife Refuge, cast your line with a fishing tour, make a trip to Chincoteague Cultural Alliance, and get a dose of the wild on a nature and wildlife tour.

For maps, traveler tips, ratings, and tourist information, you can read our Chincoteague Island trip builder app .

Drive from Virginia Beach to Chincoteague Island in 2.5 hours. Alternatively, you can take a bus; or take a bus. Expect a daytime high around 84°F in August, and nighttime lows around 68°F. On the 31st (Sat), wrap the sightseeing up by early afternoon so you can drive back home.

Things to do in Chincoteague Island

Outdoors Wildlife Parks

Side Trips

Chincoteague Bay Field Station, Assateague Lighthouse
Highlights from your plan
Nature & Wildlife Tours
Chincoteague National Wildlife Refuge ©
Museum of Chincoteague ©
Museum of Chincoteague

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