37 days in Virginia Itinerary

37 days in Virginia Itinerary

Created using Inspirock Virginia itinerary planner

Make it your trip
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Chantilly
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2
McLean
— 1 night
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3
Arlington
— 3 nights
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4
Alexandria
— 2 nights
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5
Luray
— 4 nights
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6
Damascus
— 2 nights
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7
Pembroke
— 1 night
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Natural Bridge
— 2 nights
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Shenandoah National Park
— 4 nights
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10
Doswell
— 2 nights
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11
Williamsburg
— 4 nights
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12
Virginia Beach
— 5 nights
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13
Chincoteague Island
— 6 nights
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Chantilly

Chantilly is a census-designated place (CDP) in western Fairfax County, Virginia, United States. On the 29th (Thu), examine the collection at Steven F. Udvar-Hazy Center.

To see other places to visit, ratings, maps, and tourist information, go to the Chantilly trip planner.

Winchester to Chantilly is an approximately 1.5-hour car ride. You can also do a combination of taxi, bus, and subway. In August in Chantilly, expect temperatures between 85°F during the day and 64°F at night. Wrap up your sightseeing by early afternoon on the 29th (Thu) to allow enough time to drive to McLean.

Things to do in Chantilly

Museums
Highlights from your trip

McLean

— 1 night
McLean is a census-designated place (CDP) in Fairfax County in Northern Virginia. To find ratings, other places to visit, traveler tips, and other tourist information, go to the McLean online sightseeing planner.

McLean is very close to Chantilly. Traveling from Chantilly in August, you can expect nighttime temperatures to be somewhat warmer in McLean, with lows of 71°F. Wrap up your sightseeing on the 30th (Fri) early enough to drive to Arlington.

Things to do in McLean

Parks · Nature
Highlights from your trip

Arlington

— 3 nights

National History, Local Flavor

Located just across the Potomac River from Washington, D.C., the county of Arlington blends big city and sprawling suburban environments.
Your day by day itinerary now includes Theodore Roosevelt Island Park as well as Gravelly Point Park. Start off your visit on the 30th (Fri): step off the mainland to explore Theodore Roosevelt Island Park. Get ready for a full day of sightseeing on the 31st (Sat): stroll through Mount Vernon Trail and then stroll around Gravelly Point Park.

To see photos, more things to do, reviews, and tourist information, go to the Arlington trip maker app.

Arlington is just a short distance from McLean. August in Arlington sees daily highs of 87°F and lows of 71°F at night. You'll set off for Alexandria on the 2nd (Mon).

Things to do in Arlington

Parks · Historic Sites · Trails · Outdoors

Alexandria

— 2 nights
Just a few metro stops away from the bustle of Washington D.C., Alexandria provides a respite from the fast-paced capital.
Your day by day itinerary now includes Potomac Riverboat Company as well as Jones Point Park. Kick off your visit on the 2nd (Mon): stroll around Jones Point Park, then take a leisurely stroll along Old Town Waterfront, then view the masterpieces at Torpedo Factory Art Center, and finally wander the streets of Old Town. Get ready for a full day of sightseeing on the next day: get from here to there with Potomac Riverboat Company.

To find traveler tips, photos, where to stay, and other tourist information, you can read our Alexandria trip planner.

Alexandria is just a short distance from Arlington. In September, daily temperatures in Alexandria can reach 82°F, while at night they dip to 65°F. On the 4th (Wed), you're off to Luray.

Things to do in Alexandria

Tours · Transportation · Outdoors · Parks

Luray

— 4 nights

Cabin Capital of Virginia

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.
You've now added Appalachian Adventures to your itinerary. Change things up with a short trip to Swallow Falls State Park in Oakland (about 2 hours away). There's still lots to do: Head underground at Luray Caverns, tour the pleasant surroundings at Stony Man Mountain Overlook, and get to know the resident critters at Luray Zoo - A Rescue Zoo.

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

Getting from Alexandria to Luray by car takes about 2 hours. Other options: do a combination of train and car; or do a combination of bus and taxi. Traveling from Alexandria in September, you can expect nighttime temperatures to be little chillier in Luray, with lows of 57°F. Cap off your sightseeing on the 8th (Sun) early enough to travel to Damascus.

Things to do in Luray

Parks · Outdoors · Nature · Tours

Side Trip

Damascus

— 2 nights
Damascus is a town in Washington County, Virginia, United States. Start off your visit on the 8th (Sun): stop by Mast General Store, then kick your exploration up a notch at some of the top local zipline courses and adventure parks, and then trek along Virginia Creeper National Recreation Trail. Keep things going the next day: explore by horseback at Moses H. Cone Memorial Park.

To see ratings, photos, where to stay, and more tourist information, refer to the Damascus online sightseeing planner.

Traveling by car from Luray to Damascus takes 4.5 hours. Alternatively, you can do a combination of car and flight. September in Damascus sees daily highs of 79°F and lows of 59°F at night. Wrap up your sightseeing by early afternoon on the 10th (Tue) to allow time for travel to Pembroke.

Things to do in Damascus

Outdoors · Trails · Parks · Tours

Side Trips

Pembroke

— 1 night
Pembroke is a town in Giles County, Virginia, United States. Start off your visit on the 10th (Tue): trek along Cascades National Recreation Trail, then take in the dramatic scenery at Cascade Falls, and then contemplate the long history of Sinking Creek Covered Bridge.

For reviews, ratings, photos, and tourist information, you can read our Pembroke road trip planning app.

Traveling by car from Damascus to Pembroke takes 2 hours. September in Pembroke sees daily highs of 76°F and lows of 57°F at night. Cap off your sightseeing on the 11th (Wed) early enough to go by car to Natural Bridge.

Things to do in Pembroke

Parks · Trails · Outdoors · Nature

Side Trip

Highlights from your trip

Natural Bridge

— 2 nights
Natural Bridge is an unincorporated community in Rockbridge County, Virginia, United States. Start off your visit on the 11th (Wed): look for all kinds of wild species at Virginia Safari Park, then appreciate the history behind Dinosaur Kingdom II, and then explore the striking landscape at Natural Bridge State Park. Get ready for a full day of sightseeing on the 12th (Thu): pause for some photo ops at National D-Day Memorial, then get to know the resident critters at Natural Bridge Zoo, then Head underground at Caverns At Natural Bridge, and finally don't miss a visit to Foamhenge.

To see traveler tips, other places to visit, and tourist information, use the Natural Bridge tour planner.

Getting from Pembroke to Natural Bridge by car takes about 1.5 hours. Expect slightly colder weather when traveling from Pembroke in September: highs in Natural Bridge hover around 68°F, while lows dip to 54°F. Finish up your sightseeing early on the 13th (Fri) so you can go by car to Shenandoah National Park.

Things to do in Natural Bridge

Parks · Wildlife · Nature · Historic Sites

Side Trip

Shenandoah National Park

— 4 nights
Shenandoah National Park showcases a particularly scenic section of Virginia's Blue Ridge Mountains.
Explore Shenandoah National Park's surroundings by going to Grand Caverns (in Grottoes) and SoLace Studios Fine Handcrafts (in Elkton). And it doesn't end there: stroll through Old Rag Mountain Hike, explore and take pictures at Skyline Drive, explore the different monuments and memorials at Dean Cemetery, and trek along Appalachian Trail.

To see reviews, ratings, photos, and tourist information, go to the Shenandoah National Park travel site.

You can drive from Natural Bridge to Shenandoah National Park in 2 hours. Another option is to do a combination of taxi and bus. Expect somewhat warmer temperatures when traveling from Natural Bridge in September; daily highs in Shenandoah National Park reach 80°F and lows reach 60°F. Wrap up your sightseeing on the 17th (Tue) to allow time to travel to Doswell.

Things to do in Shenandoah National Park

Parks · Nature · Outdoors · Trails

Side Trips

Doswell

— 2 nights
Doswell is an unincorporated community in Hanover County in the Central Region of the U.S. Commonwealth of Virginia. Kick off your visit on the 17th (Tue): steep yourself in history at The Rising Sun Tavern, then test your problem-solving skills at popular escape rooms, and then find something for the whole family at Kings Dominion. On the 18th (Wed), you'll have a packed day of sightseeing: steep yourself in history at Chatham Manor, take in the history at Fredericksburg & Spotsylvania National Military Park, then take in the history at Chancellorsville Battlefield Visitor Center, and finally appreciate the extensive heritage of Old Town.

Plan a Doswell trip in moments using our itinerary builder.

Drive from Shenandoah National Park to Doswell in 2.5 hours. In September, daily temperatures in Doswell can reach 80°F, while at night they dip to 61°F. Finish up your sightseeing early on the 19th (Thu) so you can go by car to Williamsburg.

Things to do in Doswell

Historic Sites · Theme Parks · Fun & Games · Museums

Side Trips

Williamsburg

— 4 nights

Colonial Capital

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 historic sites, theme parks, and shopping. Your plan includes some of its best attractions: get in on the family fun at Busch Gardens Williamsburg, cool off at Water Country USA, contemplate the long history of Yorktown Battlefield, and take an in-depth tour of Historic Jamestowne.

For photos, reviews, traveler tips, and other tourist information, you can read our Williamsburg road trip planner.

Drive from Doswell to Williamsburg in 1.5 hours. September in Williamsburg sees daily highs of 84°F and lows of 66°F at night. Wrap up your sightseeing on the 23rd (Mon) early enough to drive to Virginia Beach.

Things to do in Williamsburg

Historic Sites · Museums · Theme Parks · Shopping

Side Trip

Virginia Beach

— 5 nights

The Resort City

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.
Change things up with these side-trips from Virginia Beach: Parasailing & Paragliding (in Duck), Jockey's Ridge State Park (in Nags Head) and Wright Brothers National Memorial (in Kill Devil Hills). The adventure continues: take a leisurely stroll along Virginia Beach Boardwalk, enjoy the sea views from Cape Henry Lighthouse, enjoy the sand and surf at Sandbridge Beach, and get your game on at Tribal Axe.

To see other places to visit, ratings, and tourist information, read Virginia Beach travel itinerary planner.

Drive from Williamsburg to Virginia Beach in 1.5 hours. Alternatively, you can take a bus; or do a combination of train and bus. Expect a daytime high around 81°F in September, and nighttime lows around 67°F. Wrap up your sightseeing on the 28th (Sat) early enough to drive to Chincoteague Island.

Things to do in Virginia Beach

Parks · Outdoors · Wildlife · Museums

Side Trips

Chincoteague Island

— 6 nights
Famous for a wild breed of horses--Chincoteague Ponies--Chincoteague Island embraces the mystery of some of North America’s oldest inhabitants.
Explore Chincoteague Island's surroundings by going to Janes Island State Park (in Crisfield), Cambridge (Blackwater National Wildlife Refuge, Choptank River Lighthouse, &more) and Salisbury (Salisbury Zoo & Arthur W. Perdue Stadium (Delmarva Shorebirds)). There's still lots to do: look for all kinds of wild species at Chincoteague National Wildlife Refuge, enjoy the sea views from Assateague Lighthouse, get a dose of the wild on a nature and wildlife tour, and let little ones run wild at Chincoteague Veteran's Memorial Park.

Inspirock's itinerary builder makes planning a Chincoteague Island trip simple and quick.

Drive from Virginia Beach to Chincoteague Island in 2.5 hours. Alternatively, you can take a bus; or take a bus. In September, daily temperatures in Chincoteague Island can reach 80°F, while at night they dip to 64°F. Wrap up your sightseeing by early afternoon on the 4th (Fri) to allow time for the car ride back home.

Things to do in Chincoteague Island

Parks · Wildlife · Outdoors · Nature

Side Trips

Virginia travel guide

4.6
Historic Sites · Wineries & Vineyards · Gardens
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.