32 days in Virginia Itinerary

32 days in Virginia Itinerary

Created using Inspirock Virginia trip planner

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Route & dates

32 days in Virginia Itinerary

Start: Houston
Fly:  5​h 45​min
1
Virginia Beach
— 4 nights
Drive:  1​h 15​min
2
Williamsburg
— 5 nights
Drive:  3​h
3
Chincoteague Island
— 3 nights
Drive:  3​h 45​min
4
Arlington
— 4 nights
Drive:  1​h 30​min
5
Winchester
— 4 nights
Drive:  1​h 15​min
6
Luray
— 4 nights
Drive:  1​h 30​min
7
Charlottesville
— 5 nights
Drive:  3​h 45​min
8
Damascus
— 2 nights
Drive + Fly:  10​h 30​min
End: Houston

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.
Virginia Beach is known for beaches, childrens museums, parks, museums, and historic sites. Your plan includes some of its best attractions: take a leisurely stroll along Virginia Beach Boardwalk, identify plant and animal life at First Landing State Park, brush up on your knowledge of spirits at Tarnished Truth Distilling Company, and examine the collection at Military Aviation Museum.

To see photos, ratings, and tourist information, refer to the Virginia Beach trip itinerary app .

Houston to Virginia Beach is an approximately 6-hour flight. You can also do a combination of flight and bus; or drive. You'll lose 1 hour traveling from Houston to Virginia Beach due to the time zone difference. Prepare for a bit cooler weather when traveling from Houston in September: high temperatures in Virginia Beach hover around 81°F and lows are around 67°F. Cap off your sightseeing on the 4th (Fri) early enough to go by car to Williamsburg.

Things to do in Virginia Beach

Parks Museums Outdoors

Side Trip

Norfolk
Highlights from your plan
Tarnished Truth Distilling Company ©
Virginia Beach Boardwalk ©
Virginia Beach Boardwalk
Virginia Beach ©
Virginia Beach

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.
You'll find plenty of places to visit near Williamsburg: Newport News (USS Monitor Center & The Mariners' Museum & Park), St. Luke's Historic Church & Museum (in Smithfield) and Virginia Museum of Fine Arts (in Richmond). The adventure continues: make a splash at Busch Gardens Williamsburg, pause for some serene contemplation at Bruton Parish Episcopal Church, contemplate the long history of Historic Jamestowne, and stop by R.P. Wallace & Sons General Store.

To see photos, other places to visit, where to stay, and tourist information, refer to the Williamsburg vacation builder .

Drive from Virginia Beach to Williamsburg in 1.5 hours. Alternatively, you can take a bus; or take a bus. October in Williamsburg sees daily highs of 75°F and lows of 55°F at night. Wrap up your sightseeing on the 9th (Wed) early enough to drive to Chincoteague Island.

Things to do in Williamsburg

Museums Historic Sites Theme Parks

Side Trips

Newport News, Virginia Museum of Fine Arts, St. Luke's Historic Church & Museum
Highlights from your plan
Busch Gardens Williamsburg ©
Busch Gardens Williamsburg
Colonial Williamsburg ©
Colonial Williamsburg
Historic Jamestowne ©
Historic Jamestowne

3
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.
Chincoteague Island is known for parks, museums, outdoors, shopping, and historic sites. Your plan includes some of its best attractions: look for all kinds of wild species at Chincoteague National Wildlife Refuge, visit a coastal fixture at Assateague Lighthouse, get outside with Donald J. Leonard, and let little ones run wild at Chincoteague Veteran's Memorial Park.

To see maps, where to stay, and other tourist information, go to the Chincoteague Island visit planner .

Getting from Williamsburg to Chincoteague Island by car takes about 3 hours. Other options: take a bus. In October, daytime highs in Chincoteague Island are 71°F, while nighttime lows are 54°F. Cap off your sightseeing on the 12th (Sat) early enough to go by car to Arlington.

Things to do in Chincoteague Island

Wildlife Outdoors Parks

Side Trip

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

4
nights
Arlington

Arlington ©
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: National Museum of the Marine Corps (in Triangle), George Washington's Mount Vernon (in Mount Vernon) and Steven F. Udvar-Hazy Center (in Chantilly). The adventure continues: steep yourself in history at Arlington National Cemetery, pause for some photo ops at Pentagon Memorial, appreciate the extensive heritage of The Tomb of the Unknown Soldier, and step off the mainland to explore Theodore Roosevelt Island Park.

To find maps, reviews, other places to visit, and other tourist information, you can read our Arlington trip planner .

Getting from Chincoteague Island to Arlington by car takes about 4 hours. Other options: do a combination of bus and flight; or do a combination of taxi and bus. In October, plan for daily highs up to 71°F, and evening lows to 54°F. Wrap up your sightseeing on the 16th (Wed) early enough to drive to Winchester.

Things to do in Arlington

Historic Sites Parks Museums

Side Trips

Alexandria, Steven F. Udvar-Hazy Center, National Museum of the Marine Corps, George Washington's Mount Vernon
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

4
nights
Winchester

Winchester ©
Winchester is an independent city located in the northwestern portion of the Commonwealth of Virginia. Explore the numerous day-trip ideas around Winchester: Raven Rocks (in Bluemont), Stribling Orchard (in Markham) and Purcellville (Blue Ridge Center for Environmental Stewardship & The Washington & Old Dominion Trail). There's still lots to do: wander the wide-open spaces of Rocking S Ranch, explore the world behind art at Museum of the Shenandoah Valley, examine the collection at Stonewall Jackson's Headquarters, and stroll around Glenwood Park.

To see photos, where to stay, more things to do, and other tourist information, read our Winchester day trip website .

Getting from Arlington to Winchester by car takes about 1.5 hours. Other options: take a bus; or take a train. Traveling from Arlington in October, you can expect nighttime temperatures to be little chillier in Winchester, with lows of 46°F. Wrap up your sightseeing on the 20th (Sun) to allow time to drive to Luray.

Things to do in Winchester

Parks Outdoors Trails

Side Trips

Purcellville, Raven Rocks, Sky Meadows State Park, My Neighbor and Me, Stribling Orchard
Highlights from your plan
Rocking S Ranch ©
Rocking S Ranch
Cascade Falls ©
Cascade Falls
Museum of the Shenandoah Valley ©
Museum of the Shenandoah Valley

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.
You'll find plenty of places to visit near Luray: Buzzard Rock North (in Front Royal) and Shenandoah National Park (Skyline Drive, Appalachian Trail, & more). And it doesn't end there: take in breathtaking views at Luray Caverns, admire the natural beauty at Birdsong Pleasure Garden, take an in-depth tour of The Car and Carriage Caravan Museum, and hike along Kennedy Peak Hike.

To find ratings, more things to do, other places to visit, and more tourist information, read Luray trip website .

Traveling by car from Winchester to Luray takes 1.5 hours. In October, plan for daily highs up to 70°F, and evening lows to 48°F. Cap off your sightseeing on the 24th (Thu) early enough to go by car to Charlottesville.

Things to do in Luray

Parks Outdoors Nature

Side Trips

Shenandoah National Park, Buzzard Rock North, Copper Fox Distillery
Highlights from your plan
Luray Caverns ©
Luray Caverns
Skyline Drive ©
Skyline Drive
Stony Man Mountain Overlook ©
Stony Man Mountain Overlook

5
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.
Change things up with these side-trips from Charlottesville: Brownsburg Museum (in Brownsburg), National D-Day Memorial (in Bedford) and Appomattox Court House National Historical Park (in Appomattox). The adventure continues: stroll through Monticello, test your team's savvy at popular escape rooms, gain insight at Virginia Military Institute, and view the masterpieces at Earth, Fire, & Spirit Pottery.

To find maps, reviews, other places to visit, and other tourist information, use the Charlottesville route planner.

You can drive from Luray to Charlottesville in 1.5 hours. Another option is to do a combination of car and bus. Expect a daytime high around 71°F in October, and nighttime lows around 49°F. Wrap up your sightseeing on the 29th (Tue) to allow time to travel to Damascus.

Things to do in Charlottesville

Parks Historic Sites Wildlife

Side Trips

Lexington, Natural Bridge, National D-Day Memorial, Brownsburg Museum, Appomattox Court House National Historical Park
Highlights from your plan
National D-Day Memorial ©
National D-Day Memorial
Monticello ©
Monticello
Old Rag Mountain Hike ©
Old Rag Mountain Hike

2
nights
Damascus

Damascus ©
Damascus is a town in Washington County, Virginia, United States. Kick off your visit on the 30th (Wed): stroll the grounds of Sinking Spring Cemetery, take an in-depth tour of The Birthplace of Country Music Museum, then tour the pleasant surroundings at Virginia Creeper Trail Club, and finally tour the pleasant surroundings at Virginia Creeper National Recreation Trail.

For maps, more things to do, reviews, and tourist information, read Damascus trip itinerary planning app .

You can drive from Charlottesville to Damascus in 4 hours. Alternatively, you can do a combination of car and flight. October in Damascus sees daily highs of 69°F and lows of 49°F at night. On the 31st (Thu), wrap the sightseeing up by early afternoon so you can travel back home.

Things to do in Damascus

Parks Outdoors Trails

Side Trips

Abingdon, The Birthplace of Country Music Museum, Grayson Highlands State Park
Highlights from your plan
Grayson Highlands State Park ©
Grayson Highlands State Park
The Birthplace of Country Music Museum ©

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