39 days in Virginia Itinerary

39 days in Virginia Itinerary

Created using Inspirock Virginia tour planner

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Route & dates

39 days in Virginia Itinerary

Start: Tallinn
+2
Fly + bus + subway:  17​h 30​min
1
Arlington
— 3 nights
Drive:  1​h 30​min
2
Winchester
— 3 nights
Drive:  1​h 15​min
3
Luray
— 4 nights
Drive:  1​h 15​min
4
Shenandoah National Park
— 4 nights
Drive:  1​h 15​min
5
Charlottesville
— 4 nights
Drive:  4​h
6
Wytheville
— 4 nights
Drive:  1​h 30​min
7
Abingdon
— 4 nights
Drive:  6​h
8
Williamsburg
— 2 nights
Drive:  3​h
9
Chincoteague Island
— 4 nights
Drive:  2​h 30​min
10
Virginia Beach
— 3 nights
Fly:  17​h
End: Tallinn

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.
Explore the numerous day-trip ideas around Arlington: Steven F. Udvar-Hazy Center (in Chantilly), George Washington's Mount Vernon (in Mount Vernon) and National Museum of the Marine Corps (in Triangle). There's still lots to do: explore the different monuments and memorials at Arlington National Cemetery, don't miss a visit to John F. Kennedy Grave Site, stroll through Gravelly Point Park, and get to know the fascinating history of Tomb of the Unknowns.

To find maps, reviews, photos, and other tourist information, read Arlington road trip planning site .

Tallinn, Estonia to Arlington is an approximately 17.5-hour flight. The time zone difference moving from Eastern European Time to Eastern Standard Time is minus 7 hours. Traveling from Tallinn in November, expect Arlington to be somewhat warmer, temps between 17°C and 6°C. Finish your sightseeing early on the 27th (Tue) so you can drive to Winchester.

Things to do in Arlington

Historic Sites Parks Museums

Side Trips

Old Town, National Museum of the Marine Corps, Steven F. Udvar-Hazy Center, Quantico National Cemetery, 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

3
nights
Winchester

Winchester ©
Winchester is an independent city located in the northwestern portion of the Commonwealth of Virginia. Change things up with these side-trips from Winchester: Raven Rocks (in Bluemont), Hartland Family Orchard (in Markham) and Blue Ridge Center for Environmental Stewardship (in Purcellville). There's lots more to do: explore and take pictures at Rocking S Ranch, take in nature's colorful creations at State Arboretum of Virginia, head outdoors with Royal Horseshoe Farm, and tour the pleasant surroundings at Sherando Park.

Planning Winchester trip won't be overwheling when you use's Insprock itinerary maker.

Traveling by car from Arlington to Winchester takes 1.5 hours. Prepare for a bit cooler weather when traveling from Arlington in November: high temperatures in Winchester hover around 14°C and lows are around 1°C. Finish your sightseeing early on the 30th (Fri) so you can drive to Luray.

Things to do in Winchester

Parks Outdoors Trails

Side Trips

Front Royal, Blue Ridge Center for Environmental Stewardship, Hartland Family Orchard, State Arboretum of Virginia, Raven Rocks
Highlights from your plan
Rocking S Ranch ©
Rocking S Ranch
Raven Rocks ©
Raven Rocks

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: Woodstock (Big Schloss & W.O. Riley Park) and Culpeper National Cemetery (in Culpeper). The adventure continues: take in breathtaking views at Luray Caverns, trek along Massanutten Storybook Trail, stroll through Kennedy Peak Hike, and brush up on your knowledge of spirits at Copper Fox Distillery.

Make your Luray itinerary with Inspirock to find out what to see and where to go.

You can drive from Winchester to Luray in 1.5 hours. In November, plan for daily highs up to 16°C, and evening lows to 1°C. Cap off your sightseeing on the 4th (Tue) early enough to go by car to Shenandoah National Park.

Things to do in Luray

Parks Outdoors Trails

Side Trips

Sperryville, Woodstock, Culpeper National Cemetery
Highlights from your plan
Luray Caverns ©
Luray Caverns
Stony Man Mountain Hike ©
Stony Man Mountain Hike
Birdsong Pleasure Garden ©
Birdsong Pleasure Garden

4
nights
Shenandoah National Park

Shenandoah National Park ©
Shenandoah National Park showcases a particularly scenic section of Virginia's Blue Ridge Mountains.
When in Shenandoah National Park, make a side trip to see Sherando Lake Family Recreation Area Campground in Lyndhurst, approximately 54 minutes away. And it doesn't end there: cruise along Skyline Drive, tour the pleasant surroundings at Old Rag Mountain Hike, take in the awesome beauty at Bearfence Mountain, and identify plant and animal life at Elkwallow Picnic Area.

Plan my day in Shenandoah National Park using traveler tips and tourist information provided by Inspirock.

Drive from Luray to Shenandoah National Park in 1.5 hours. In December, daily temperatures in Shenandoah National Park can reach 13°C, while at night they dip to 1°C. Finish your sightseeing early on the 8th (Sat) so you can drive to Charlottesville.

Things to do in Shenandoah National Park

Parks Outdoors Nature

Side Trip

Sherando Lake Family Recreation Area Campground
Highlights from your plan
Old Rag Mountain Hike ©
Old Rag Mountain Hike
Skyline Drive ©
Skyline Drive
Appalachian Trail ©
Appalachian Trail

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.
Get out of town with these interesting Charlottesville side-trips: Presbyterian Cemetery (in Lynchburg), National D-Day Memorial (in Bedford) and Staunton (Star B Stables & Trinity Episcopal Church). Spend the 11th (Tue) exploring nature at Ivy Creek Natural Area. And it doesn't end there: explore the galleries of Thomas Jefferson's Monticello, deepen your understanding at University of Virginia, experience rural life at Open Gate Farm, and explore and take pictures at Virginia Military Institute.

To see other places to visit, maps, ratings, and tourist information, use the Charlottesville day trip website .

Traveling by car from Shenandoah National Park to Charlottesville takes 1.5 hours. Alternatively, you can do a combination of taxi and bus. In December in Charlottesville, expect temperatures between 13°C during the day and 1°C at night. Finish your sightseeing early on the 12th (Wed) to allow enough time to travel to Wytheville.

Things to do in Charlottesville

Parks Outdoors Trails

Side Trips

Staunton, National D-Day Memorial, Open Gate Farm, Presbyterian Cemetery, Virginia Military Institute
Highlights from your plan
National D-Day Memorial ©
National D-Day Memorial
Monticello ©
Monticello
Virginia Military Institute ©
Virginia Military Institute

4
nights
Wytheville

Wytheville ©
Wytheville is a town in, and the county seat of, Wythe County, Virginia, United States. Explore Wytheville's surroundings by going to Pete Dye River Course of Virginia Tech (in Radford), Hahn Horticulture Garden at Virginia Tech (in Blacksburg) and Blue Ridge Music Center (in Galax). There's lots more to do: stroll through Mount Rogers National Recreation Area, take an in-depth tour of Wythe County Historical and Genealogical Research Center, see the interesting displays at Edith Bolling Wilson Birthplace Museum, and contemplate the long history of Haller-Gibboney Rock House.

For reviews, maps, traveler tips, and tourist information, read our Wytheville road trip planning app .

Getting from Charlottesville to Wytheville by car takes about 3 hours. In December, daytime highs in Wytheville are 10°C, while nighttime lows are 0°C. Finish up your sightseeing early on the 16th (Sun) so you can travel to Abingdon.

Things to do in Wytheville

Parks Museums Outdoors

Side Trips

Floyd, Pete Dye River Course of Virginia Tech, Lincolnshire Park, Blue Ridge Music Center, West Wind Farm Vineyard & Winery
Highlights from your plan
Blue Ridge Music Center ©
Blue Ridge Music Center
Lincolnshire Park ©
Lincolnshire Park

4
nights
Abingdon

Abingdon ©
Abingdon is a town in Washington County, Virginia, United States, southwest of Roanoke. Explore Abingdon's surroundings by going to The Channels Natural Area Preserve (in Lebanon), Virginia Creeper Trail (in Damascus) and Grayson Highlands State Park (in Mouth of Wilson). And it doesn't end there: hike along Virginia Creeper Trail Club, explore the different monuments and memorials at Sinking Spring Cemetery, tour the pleasant surroundings at The Devil's Bathtub, and take an in-depth tour of Historical Society of Washington County, VA.

For other places to visit, more things to do, ratings, and other tourist information, read Abingdon holiday maker website .

Drive from Wytheville to Abingdon in an hour. In December, plan for daily highs up to 12°C, and evening lows to 1°C. Wrap up your sightseeing on the 20th (Thu) early enough to travel to Williamsburg.

Things to do in Abingdon

Parks Outdoors Trails

Side Trips

Bristol, Grayson Highlands State Park, The Channels Natural Area Preserve, Virginia Creeper Trail, The Devil's Bathtub
Highlights from your plan
Grayson Highlands State Park ©
Grayson Highlands State Park
Virginia Creeper Trail Club ©
Virginia Creeper Trail Club
Birthplace of Country Music Museum ©
Birthplace of Country Music Museum

2
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.
Pack the 22nd (Sat) with family-friendly diversions at Busch Gardens Williamsburg. And it doesn't end there: steep yourself in history at Colonial Williamsburg, get engrossed in the history at Historic Jamestowne, take in the architecture and atmosphere at Bruton Parish Episcopal Church, and explore the striking landscape of Colonial National Historic Park.

For other places to visit, more things to do, ratings, and other tourist information, go to the Williamsburg travel planner.

Getting from Abingdon to Williamsburg by car takes about 5.5 hours. Other options: fly. In December, daytime highs in Williamsburg are 15°C, while nighttime lows are 3°C. Finish your sightseeing early on the 23rd (Sun) so you can drive to Chincoteague Island.

Things to do in Williamsburg

Historic Sites Theme Parks Museums
Highlights from your plan
Colonial Williamsburg ©
Colonial Williamsburg
Busch Gardens Williamsburg ©
Busch Gardens Williamsburg
Historic Jamestowne ©
Historic Jamestowne

4
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.
Spend the 24th (Mon) exploring nature at Chincoteague National Wildlife Refuge. There's much more to do: get outside with Donald J. Leonard, explore the landscape on two wheels at Bike Depot, let the kids burn off some steam at Chincoteague Veteran's Memorial Park, and view the masterpieces at Tryfan Gallery.

To find traveler tips, ratings, maps, and other tourist information, refer to the Chincoteague Island trip itinerary planner.

You can drive from Williamsburg to Chincoteague Island in 3 hours. Another option is to take a bus. In December, daytime highs in Chincoteague Island are 13°C, while nighttime lows are 2°C. Cap off your sightseeing on the 27th (Thu) early enough to go by car to Virginia Beach.

Things to do in Chincoteague Island

Wildlife Outdoors Parks
Highlights from your plan
Chincoteague National Wildlife Refuge ©
Nature & Wildlife Tours
Chincoteague Cultural Alliance ©
Chincoteague Cultural Alliance

3
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 Weyanoke Bird and Wildflower Sanctuary (in Norfolk) and St. Luke's Historic Church & Museum (in Smithfield). The adventure continues: take in the waterfront at Virginia Beach Boardwalk, appreciate the history behind Naval Aviation Monument, tour the pleasant surroundings at Sandbridge Beach, and admire the masterpieces at Chrysler Museum of Art.

You can plan Virginia Beach trip in no time by asking Inspirock to help create your itinerary.

You can drive from Chincoteague Island to Virginia Beach in 2.5 hours. Other options are to take a bus; or take a bus. In December, daily temperatures in Virginia Beach can reach 15°C, while at night they dip to 4°C. Wrap up your sightseeing on the 30th (Sun) to allow time to travel back home.

Things to do in Virginia Beach

Parks Museums Beaches

Side Trips

Norfolk, St. Luke's Historic Church & Museum
Highlights from your plan
St. Luke's Historic Church & Museum ©
Virginia Beach Boardwalk ©
Virginia Beach Boardwalk
Military Aviation Museum ©
Military Aviation Museum

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