31 days in Virginia Itinerary

31 days in Virginia Itinerary

Created using Inspirock Virginia route planner
Make it your trip
Drive
1
Chincoteague Island
— 2 nights
Drive
2
Virginia Beach
— 4 nights
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3
Williamsburg
— 4 nights
Drive
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Charlottesville
— 4 nights
Drive
5
Damascus
— 1 night
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6
Shenandoah National Park
— 4 nights
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7
Luray
— 4 nights
Drive
8
Winchester
— 3 nights
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9
Arlington
— 4 nights
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Chincoteague Island — 2 nights

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, and museums. Your trip includes some of its best attractions: explore the striking landscape of Chincoteague National Wildlife Refuge, tour the pleasant surroundings at Bike Depot, take an in-depth tour of Museum of Chincoteague, and enjoy the sea views from Assateague Lighthouse.

To find more things to do, ratings, traveler tips, and other tourist information, read our Chincoteague Island road trip app.

Washington DC to Chincoteague Island is an approximately 3.5-hour car ride. You can also do a combination of train, bus, and taxi; or take a bus. In July, daytime highs in Chincoteague Island are 86°F, while nighttime lows are 72°F. Wrap up your sightseeing on the 3rd (Fri) to allow time to drive to Virginia Beach.
Parks · Wildlife · Nature · Fun & Games
Side Trip

Virginia Beach — 4 nights

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.
Virginia Beach is known for sightseeing, beaches, and zoos & aquariums. Your trip includes some of its best attractions: take a leisurely stroll along Virginia Beach Boardwalk, brush up on your knowledge of spirits at Tarnished Truth Distilling Company, brush up on your military savvy at Military Aviation Museum, and immerse yourself in nature at First Landing State Park.

To find other places to visit, more things to do, traveler tips, and more tourist information, read our Virginia Beach trip itinerary maker app.

You can drive from Chincoteague Island to Virginia Beach in 2.5 hours. Alternatively, you can take a bus; or take a bus. July in Virginia Beach sees daily highs of 89°F and lows of 73°F at night. Wrap up your sightseeing on the 7th (Tue) to allow time to drive to Williamsburg.
Parks · Museums · Outdoors · Beaches
Side Trip

Williamsburg — 4 nights

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.
Williamsburg is known for museums, theme parks, and historic sites. Your trip includes some of its best attractions: find something for the whole family at Busch Gardens Williamsburg, get engrossed in the history at Colonial Williamsburg, contemplate the long history of Bassett Hall, and explore the galleries of Historic Jamestowne.

For maps, where to stay, photos, and more tourist information, read our Williamsburg trip itinerary maker tool.

Getting from Virginia Beach to Williamsburg by car takes about 1.5 hours. Other options: take a bus; or do a combination of bus and train. In July, daily temperatures in Williamsburg can reach 91°F, while at night they dip to 73°F. Cap off your sightseeing on the 11th (Sat) early enough to go by car to Charlottesville.
Historic Sites · Theme Parks · Museums · Tours

Charlottesville — 4 nights

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.
Venture out of the city with trips to National D-Day Memorial (in Bedford), James Madison's Montpelier (in Montpelier Station) and Natural Bridge State Park (in Natural Bridge). There's lots more to do: take in nature's colorful creations at Monticello, gain insight at Virginia Military Institute, experience rural life at Carter Mountain Orchard, and pause for some serene contemplation at Saint Francis of Assisi Catholic Church.

For other places to visit, maps, reviews, and tourist information, read our Charlottesville itinerary maker site.

Traveling by car from Williamsburg to Charlottesville takes 2.5 hours. Alternatively, you can take a bus; or do a combination of train and bus. Traveling from Williamsburg in July, plan for little chillier nights in Charlottesville, with lows around 68°F. Finish up your sightseeing early on the 15th (Wed) so you can travel to Damascus.
Historic Sites · Parks · Nature · Museums
Side Trips

Damascus — 1 night

Damascus is a town in Washington County, Virginia, United States. Kick off your visit on the 16th (Thu): hike along Appalachian Trail, then grab your bike and head to Adventure Damascus, and then trek along Virginia Creeper National Recreation Trail.

To see other places to visit, where to stay, and other tourist information, refer to the Damascus road trip tool.

Traveling by car from Charlottesville to Damascus takes 4 hours. Alternatively, you can do a combination of car and flight. Expect a daytime high around 84°F in July, and nighttime lows around 66°F. Finish up your sightseeing early on the 16th (Thu) so you can travel to Shenandoah National Park.
Outdoors · Parks · Trails
Side Trips

Shenandoah National Park — 4 nights

Shenandoah National Park showcases a particularly scenic section of Virginia's Blue Ridge Mountains.
Step out of Shenandoah National Park to go to Grottoes and see Grand Caverns, which is approximately 50 minutes away. There's lots more to do: explore and take pictures at Skyline Drive, explore the different monuments and memorials at Dean Cemetery, admire the sheer force of Dark Hollow Falls, and take your sightseeing to a higher altitude at Bearfence Mountain.

To see ratings, where to stay, more things to do, and more tourist information, read our Shenandoah National Park planning tool.

Drive from Damascus to Shenandoah National Park in 4.5 hours. Alternatively, you can do a combination of car and flight. In July, daily temperatures in Shenandoah National Park can reach 88°F, while at night they dip to 68°F. Finish your sightseeing early on the 20th (Mon) to allow enough time to drive to Luray.
Parks · Outdoors · Nature · Trails
Side Trip

Luray — 4 nights

Nestled in the heart of the valley formed by the Shenandoah River, Luray draws visitors with a vast underground cavern system adorned with stalactites, stalagmites, and mirrored pools.
Get out of town with these interesting Luray side-trips: Harrisonburg (A Dream Come True Playground, Explore More Discovery Museum, &more). There's much more to do: explore the fascinating underground world of Luray Caverns, whizz through the canopy at some of the top local zipline courses and adventure parks, witness the site of a historic battle at New Market State Historical Park, and walk around Shenandoah River State Park.

To plan Luray vacation without wasting time, ask Inspirock to design an itinerary.

Traveling by car from Shenandoah National Park to Luray takes 1.5 hours. In July, plan for daily highs up to 86°F, and evening lows to 66°F. Finish your sightseeing early on the 24th (Fri) to allow enough time to drive to Winchester.
Parks · Outdoors · Nature · Museums
Side Trips

Winchester — 3 nights

Winchester is an independent city located in the northwestern portion of the Commonwealth of Virginia. Explore the numerous day-trip ideas around Winchester: Cascade Falls (in Pembroke), Catoctin Creek Distillery (in Purcellville) and Fox Meadow Winery (in Linden). There's lots more to do: get a taste of life in the country at Rocking S Ranch, admire the masterpieces at Museum of the Shenandoah Valley, look for gifts at My Neighbor And Me, and take an in-depth tour of Stonewall Jackson's Headquarters.

To see photos, maps, reviews, and other tourist information, read Winchester trip itinerary builder tool.

Traveling by car from Luray to Winchester takes 1.5 hours. In July in Winchester, expect temperatures between 85°F during the day and 65°F at night. Finish up your sightseeing early on the 27th (Mon) so you can go by car to Arlington.
Museums · Parks · Childrens Museums · Nature
Side Trips

Arlington — 4 nights

Located just across the Potomac River from Washington, D.C., the county of Arlington blends big city and sprawling suburban environments.
Change things up with these side-trips from Arlington: iFLY Indoor Skydiving - Loudoun (in Ashburn), Steven F. Udvar-Hazy Center (in Chantilly) and George Washington's Mount Vernon (in Mount Vernon). There's lots more to do: explore the different monuments and memorials at Arlington National Cemetery, get to know the fascinating history of The Tomb of the Unknown Soldier, contemplate the long history of Little Library, and don't miss a visit to John F. Kennedy Grave Site.

To find more things to do, maps, other places to visit, and more tourist information, read Arlington vacation planning tool.

Traveling by car from Winchester to Arlington takes 1.5 hours. Alternatively, you can do a combination of taxi and bus; or do a combination of taxi, train, and bus. Traveling from Winchester in July, Arlington is a bit warmer at night with lows of 73°F. Finish your sightseeing early on the 31st (Fri) to allow enough time to drive back home.
Historic Sites · Museums · Parks · Nature
Side Trips

Virginia travel guide

4.6
History Museums · Wineries & Vineyards · Historic Sites
Old Dominion
The home of the first permanent English colony in the New World, Virginia is a prime holiday destination for those looking to immerse themselves in American heritage. Proud of its colorful history, distinct culture, and southern drawl, Virginians see their state as the place where the imaginary line between the north and the south is drawn. With scenic beauties as diverse as its people, Virginia is a land of rolling hills, rugged mountains, lush valleys, dense forests, and secluded beaches along picturesque bays. Bordered on the east by the Atlantic and the west by the Appalachian Mountains, with rolling farmland in the middle, the state offers countless places to visit for history buffs, nature lovers, and passionate foodies.