37 days in Virginia Itinerary

37 days in Virginia Itinerary

Created using Inspirock Virginia itinerary planner

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Route & dates

37 days in Virginia Itinerary

Start: Winchester
Drive:  1​h 30​min
1
Chantilly
— Few hours
Drive:  30​min
2
McLean
— 1 night
Drive:  30​min
3
Arlington
— 3 nights
subway:  30​min
4
Alexandria
— 2 nights
Drive:  2​h
5
Luray
— 4 nights
Drive:  4​h 15​min
6
Damascus
— 2 nights
Drive:  2​h
7
Pembroke
— 1 night
Drive:  1​h 30​min
8
Natural Bridge
— 2 nights
Drive:  1​h 45​min
9
Shenandoah National Park
— 4 nights
Drive:  1​h 45​min
10
Doswell
— 2 nights
Drive:  1​h 15​min
11
Williamsburg
— 4 nights
Drive:  1​h 15​min
12
Virginia Beach
— 5 nights
Drive:  2​h 30​min
13
Chincoteague Island
— 6 nights
Drive:  5​h
End: Winchester

few
hours
Chantilly

Chantilly ©
Chantilly is a census-designated place (CDP) in western Fairfax County, Virginia, United States. Kick off your visit on the 29th (Thu): see the interesting displays at Steven F. Udvar-Hazy Center.

For other places to visit, photos, where to stay, and other tourist information, you can read our Chantilly visit planner .

Winchester to Chantilly is an approximately 1.5-hour car ride. You can also take a bus. In August, daytime highs in Chantilly are 85°F, while nighttime lows are 64°F. 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
Find places to stay Aug 29 — 30:
Highlights from your plan
Steven F. Udvar-Hazy Center ©
Steven F. Udvar-Hazy Center

1
night
McLean

McLean ©
McLean is a census-designated place (CDP) in Fairfax County in Northern Virginia. For traveler tips, where to stay, more things to do, and tourist information, refer to the McLean online trip itinerary builder .

McLean is very close to Chantilly. Traveling from Chantilly in August, plan for somewhat warmer nights in McLean, with lows around 71°F. Finish your sightseeing early on the 30th (Fri) so you can drive to Arlington.

Things to do in McLean

Parks Nature
Find places to stay Aug 29 — 30:
Highlights from your plan
Great Falls Park ©
Great Falls Park

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.
Your day-by-day itinerary now includes Theodore Roosevelt Island Park as well as Gravelly Point Park. On the 30th (Fri), step off the mainland to explore Theodore Roosevelt Island Park. Here are some ideas for day two: explore the landscape on two wheels at Mount Vernon Trail and then walk around Gravelly Point Park.

For more things to do, ratings, reviews, and other tourist information, use the Arlington online trip itinerary planner .

Arlington is just a short distance from McLean. In August, daily temperatures in Arlington can reach 87°F, while at night they dip to 71°F. On the 2nd (Mon), you're off toAlexandria.

Things to do in Arlington

Parks Historic Sites Trails
Find places to stay Aug 30 — Sep 2:
Highlights from your plan
Mount Vernon Trail ©
Mount Vernon Trail
Theodore Roosevelt Island Park ©
Theodore Roosevelt Island Park
Gravelly Point Park
Gravelly Point Park

2
nights
Alexandria

Alexandria ©
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): walk around Jones Point Park, take a leisurely stroll along Old Town Waterfront, then take in the exciting artwork at Torpedo Factory Art Center, and finally take a stroll through Old Town. On the 3rd (Tue), you'll have a packed day of sightseeing: step on board at Potomac Riverboat Company.

For more things to do, other places to visit, photos, and other tourist information, read Alexandria day trip site .

Alexandria is very close to Arlington. September in Alexandria sees daily highs of 82°F and lows of 65°F at night. On the 4th (Wed), you'll travel to Luray.

Things to do in Alexandria

Tours Transportation Outdoors
Find places to stay Sep 2 — 4:
Highlights from your plan
Potomac Riverboat Company ©
Potomac Riverboat Company
Old Town ©
Old Town
Old Town Waterfront ©
Old Town Waterfront

4
nights
Luray

Luray ©
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.
Appalachian Adventures has been added to your itinerary. Go for a jaunt from Luray to Oakland to see Swallow Falls State Park about 2 hours away. There's still lots to do: explore the stunning scenery at Luray Caverns, admire nature's wide array of creatures at Luray Zoo - A Rescue Zoo, and stroll through Stony Man Mountain Overlook.

For ratings, traveler tips, and tourist information, you can read our Luray trip planning site .

Drive from Alexandria to Luray in 2 hours. Alternatively, you can do a combination of train and car; or do a combination of bus and taxi. Expect a bit cooler evenings in Luray when traveling from Alexandria in September, with lows around 57°F. Wrap up your sightseeing on the 8th (Sun) early enough to travel to Damascus.

Things to do in Luray

Parks Outdoors Nature

Side Trip

Swallow Falls State Park
Find places to stay Sep 4 — 8:
Highlights from your plan
Luray Caverns ©
Luray Caverns
Stony Man Mountain Overlook ©
Stony Man Mountain Overlook
Swallow Falls State Park ©
Swallow Falls State Park

2
nights
Damascus

Damascus ©
Damascus is a town in Washington County, Virginia, United States. Kick off your visit on the 8th (Sun): look for gifts at Mast General Store, then whizz through the canopy at some of the top local zipline courses and adventure parks, and then trek along Virginia Creeper National Recreation Trail. On the 9th (Mon), you'll have a packed day of sightseeing: ride a horse along Moses H. Cone Memorial Park and then relax and float downstream with a rafting and tubing tour.

To find other places to visit, traveler tips, maps, and more tourist information, read Damascus trip itinerary planning tool .

Getting from Luray to Damascus by car takes about 4.5 hours. Other options: do a combination of car and flight. In September, daily temperatures in Damascus can reach 79°F, while at night they dip to 59°F. Finish up your sightseeing early on the 10th (Tue) so you can travel to Pembroke.

Things to do in Damascus

Outdoors Tours Adventure

Side Trips

Blowing Rock, Mast General Store, River Rafting & Tubing
Find places to stay Sep 8 — 10:
Highlights from your plan
Zipline
River Rafting & Tubing

1
night
Pembroke

Pembroke ©
Pembroke is a town in Giles County, Virginia, United States. Kick off your visit on the 10th (Tue): hike along Cascades National Recreation Trail, admire the sheer force of Cascade Falls, and then steep yourself in history at Sinking Creek Covered Bridge.

To see more things to do, other places to visit, maps, and tourist information, refer to the Pembroke trip planner.

Traveling by car from Damascus to Pembroke takes 2 hours. In September, daytime highs in Pembroke are 76°F, while nighttime lows are 57°F. Wrap up your sightseeing on the 11th (Wed) early enough to drive to Natural Bridge.

Things to do in Pembroke

Parks Trails Outdoors

Side Trip

Sinking Creek Covered Bridge
Find places to stay Sep 10 — 11:
Highlights from your plan
Cascade Falls ©
Cascade Falls

2
nights
Natural Bridge

Natural Bridge ©
Natural Bridge is an unincorporated community in Rockbridge County, Virginia, United States. Kick off your visit on the 11th (Wed): identify plant and animal life at Virginia Safari Park, take in the pleasant sights at Dinosaur Kingdom II, and then take in the dramatic natural features at Natural Bridge State Park. Keep things going the next day: pause for some photo ops at National D-Day Memorial, then learn about wildlife with up-close encounters at Natural Bridge Zoo, then Head underground at Caverns At Natural Bridge, and finally make a trip to Foamhenge.

To find reviews, ratings, and tourist information, read our Natural Bridge trip planner .

Traveling by car from Pembroke to Natural Bridge takes 1.5 hours. While traveling from Pembroke, expect slightly colder days and about the same nights in Natural Bridge, ranging from highs of 68°F to lows of 54°F. Cap off your sightseeing on the 13th (Fri) early enough to go by car to Shenandoah National Park.

Things to do in Natural Bridge

Parks Wildlife Nature

Side Trip

National D-Day Memorial
Find places to stay Sep 11 — 13:
Highlights from your plan
Virginia Safari Park ©
Virginia Safari Park
Natural Bridge State Park ©
Natural Bridge State Park
Caverns At Natural Bridge ©
Caverns At Natural Bridge

4
nights
Shenandoah National Park

Shenandoah National Park ©
Shenandoah National Park showcases a particularly scenic section of Virginia's Blue Ridge Mountains.
Venture out of the city with trips to Grand Caverns (in Grottoes) and SoLace Studios Fine Handcrafts (in Elkton). And it doesn't end there: tour the pleasant surroundings at Old Rag Mountain Hike, take in the awesome beauty at Skyland, cruise along Skyline Drive, and take in the dramatic scenery at Dark Hollow Falls.

To see more things to do, maps, traveler tips, and more tourist information, use the Shenandoah National Park road trip planning website .

You can drive from Natural Bridge to Shenandoah National Park in 2 hours. Another option is to do a combination of bus and taxi. Traveling from Natural Bridge in September, things will get somewhat warmer in Shenandoah National Park: highs are around 80°F and lows about 60°F. Wrap up your sightseeing on the 17th (Tue) early enough to travel to Doswell.

Things to do in Shenandoah National Park

Parks Nature Outdoors

Side Trips

Grand Caverns, Black Bear Art Studio, SoLace Studios Fine Handcrafts
Find places to stay Sep 13 — 17:
Highlights from your plan
Old Rag Mountain Hike ©
Old Rag Mountain Hike
Skyline Drive ©
Skyline Drive
Grand Caverns ©
Grand Caverns

2
nights
Doswell

Doswell ©
Doswell is an unincorporated community in Hanover County in the Central Region of the U.S. Start off your visit on the 17th (Tue): take an in-depth tour of 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, then steep yourself in history at Chatham Manor, then take in the history at Chancellorsville Battlefield Visitor Center, and finally appreciate the extensive heritage of Old Town.

For traveler tips, reviews, photos, and more tourist information, read Doswell day trip planning website .

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

Things to do in Doswell

Historic Sites Theme Parks Fun & Games

Side Trips

Fredericksburg, Room Escape Games, Chancellorsville Battlefield Visitor Center
Find places to stay Sep 17 — 19:
Highlights from your plan
Kings Dominion ©
Kings Dominion
Room Escape Games

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.
Williamsburg is known for historic sites, theme parks, shopping, museums, and wineries. Your plan includes some of its best attractions: cool off at Busch Gardens Williamsburg, take a tour of Jamestown Settlement, steep yourself in history at Colonial Williamsburg, and witness the site of a historic battle at American Revolution Museum at Yorktown.

To see ratings, photos, reviews, and tourist information, you can read our Williamsburg trip planner .

You can drive from Doswell to Williamsburg in 1.5 hours. In September, daily temperatures in Williamsburg can reach 84°F, while at night they dip to 66°F. Finish your sightseeing early on the 23rd (Mon) to allow enough time to drive to Virginia Beach.

Things to do in Williamsburg

Historic Sites Museums Theme Parks

Side Trip

Yorktown
Find places to stay Sep 19 — 23:
Highlights from your plan
Busch Gardens Williamsburg ©
Busch Gardens Williamsburg
Water Country USA ©
Water Country USA
Jamestown Settlement ©
Jamestown Settlement

5
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.
Explore Virginia Beach's surroundings by going to Jockey's Ridge State Park (in Nags Head), Parasailing & Paragliding (in Duck) and Wright Brothers National Memorial (in Kill Devil Hills). And it doesn't end there: take in the waterfront at Virginia Beach Boardwalk, get up close and personal with brilliant marine life at Virginia Aquarium & Marine Science Center, admire the majestic nature at First Landing State Park, and visit a coastal fixture at Cape Henry Lighthouse.

To see other places to visit, ratings, more things to do, and other tourist information, go to the Virginia Beach online trip maker .

Traveling by car from Williamsburg to Virginia Beach takes 1.5 hours. Alternatively, you can take a bus; or take a bus. Expect a daytime high around 81°F in September, and nighttime lows around 67°F. Cap off your sightseeing on the 28th (Sat) early enough to go by car to Chincoteague Island.

Things to do in Virginia Beach

Parks Outdoors Museums

Side Trips

Parasailing & Paragliding, Jockey's Ridge State Park, Wright Brothers National Memorial
Find places to stay Sep 23 — 28:
Highlights from your plan
Virginia Beach ©
Virginia Beach
Jockey's Ridge State Park ©
Jockey's Ridge State Park
Parasailing & Paragliding

6
nights
Chincoteague Island

Chincoteague Island ©
Famous for a wild breed of horses--Chincoteague Ponies--Chincoteague Island embraces the mystery of some of North America’s oldest inhabitants.
Change things up with these side-trips from Chincoteague Island: Cambridge (Blackwater National Wildlife Refuge, Choptank River Lighthouse, & more), Salisbury (Salisbury Zoo & Arthur W. Perdue Stadium (Delmarva Shorebirds)) and Janes Island State Park (in Crisfield). There's still lots to do: explore the striking landscape of Chincoteague National Wildlife Refuge, head outdoors with Donald J. Leonard, get your game on at Funland Amusements, and let little ones run wild at Chincoteague Veteran's Memorial Park.

For more things to do, other places to visit, ratings, and more tourist information, refer to the Chincoteague Island road trip site .

You can drive from Virginia Beach to Chincoteague Island in 2.5 hours. Other options are to take a bus; or take a bus. In September, daytime highs in Chincoteague Island are 80°F, while nighttime lows are 64°F. Wrap up your sightseeing by early afternoon on the 4th (Fri) to allow enough time to drive back home.

Things to do in Chincoteague Island

Parks Wildlife Outdoors

Side Trips

Cambridge, Salisbury, Assateague Lighthouse, Janes Island State Park, Bishop's Stock Fine Art, Craft & Wine
Find places to stay Sep 28 — Oct 4:
Highlights from your plan
Chincoteague National Wildlife Refuge ©
Nature & Wildlife Tours
Fishing Charters & Tours

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