56 days in Virginia Itinerary

56 days in Virginia Itinerary

Created using Inspirock Virginia trip itinerary builder
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Fly to Washington Dulles International Airport, Drive to Winchester
1
Winchester
— 5 nights
Drive
2
Alexandria
— 6 nights
Drive
3
Chincoteague Island
— 5 nights
Drive
4
Virginia Beach
— 6 nights
Drive
5
Williamsburg
— 6 nights
Fly
6
Abingdon
— 6 nights
Drive
7
Mouth of Wilson
— 1 night
Drive
8
Floyd
— 3 nights
Drive
9
Bedford
— 4 nights
Drive
10
Charlottesville
— 6 nights
Drive
11
Luray
— 7 nights
Drive to Washington Dulles International Airport, Fly to Exeter

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Winchester — 5 nights

Winchester is an independent city located in the northwestern portion of the Commonwealth of Virginia. You'll find plenty of places to visit near Winchester: Front Royal (Shenandoah Valley Golf Club & Royal Horseshoe Farm), Purcellville (The Washington & Old Dominion Trail, Catoctin Creek Distillery, &more) and Hartland Family Orchard (in Markham). The adventure continues: wander the wide-open spaces of Rocking S Ranch, steep yourself in history at Belle Grove Plantation, explore the world behind art at Museum of the Shenandoah Valley, and look for gifts at Marker-Miller Orchards.

To see more things to do, traveler tips, and more tourist information, read Winchester online journey maker.

Exeter, UK to Winchester is an approximately 15-hour combination of flight and car. The time zone difference when traveling from Exeter to Winchester is minus 5 hours. In September in Winchester, expect temperatures between 30°C during the day and 15°C at night. Wrap up your sightseeing on the 10th (Sat) early enough to drive to Alexandria.
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Museums · Parks · Outdoors · Shopping
Side Trips
Find places to stay Sep 5 — 10:

Alexandria — 6 nights

Just a few metro stops away from the bustle of Washington D.C., Alexandria provides a respite from the fast-paced capital.
Change things up with these side-trips from Alexandria: Patawomeck Park (in Stafford), National Museum of the Marine Corps (in Triangle) and Hugh Mercer Apothecary Shop (in Fredericksburg). The adventure continues: contemplate the long history of Arlington National Cemetery, explore the world behind art at Virginia Museum of Fine Arts, take in the history at Manassas National Battlefield Park, and see the interesting displays at Steven F. Udvar-Hazy Center.

To see more things to do, maps, photos, and more tourist information, you can read our Alexandria tour planner.

You can drive from Winchester to Alexandria in 2 hours. Alternatively, you can do a combination of taxi, bus, and subway; or do a combination of taxi and train. Plan for a bit warmer nights when traveling from Winchester in September since evenings lows in Alexandria dip to 21°C. Wrap up your sightseeing on the 16th (Fri) to allow time to drive to Chincoteague Island.
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Historic Sites · Museums · Parks · Outdoors
Side Trips
Find places to stay Sep 10 — 16:

Chincoteague Island — 5 nights

Famous for a wild breed of horses--Chincoteague Ponies--Chincoteague Island embraces the mystery of some of North America’s oldest inhabitants.
Get out of town with these interesting Chincoteague Island side-trips: Onancock (Ten Good Sheep & Ker Place). Spend the 17th (Sat) exploring nature at Chincoteague National Wildlife Refuge. There's much more to do: see majestic marine mammals with a dolphin and whale watching tour, take in the pleasant sights at Chincoteague Island Waterman's Memorial, take a leisurely stroll along Robert N. Reed Downtown Waterfront Park, and view the masterpieces at Tryfan Gallery.

For more things to do, reviews, and tourist information, read Chincoteague Island itinerary planner.

You can drive from Alexandria to Chincoteague Island in 4 hours. Alternatively, you can do a combination of subway, train, bus, and taxi; or do a combination of flight and bus. Expect a daytime high around 31°C in September, and nighttime lows around 20°C. Finish your sightseeing early on the 21st (Wed) to allow enough time to drive to Virginia Beach.
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Parks · Wildlife · Nature · Museums
Side Trips
Find places to stay Sep 16 — 21:

Virginia Beach — 6 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.
Get out of town with these interesting Virginia Beach side-trips: Blandford Church and Cemetery (in Petersburg), Chesapeake Bay Bridge-Tunnel (in Cape Charles) and Keystone Tractor Works (in Colonial Heights). And it doesn't end there: take a leisurely stroll along Virginia Beach Boardwalk, admire the majestic nature at First Landing State Park, kick back and relax at Virginia Beach, and take a memorable tour with Tours.

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

Traveling by car from Chincoteague Island to Virginia Beach takes 2.5 hours. Alternatively, you can take a bus; or take a bus. Expect a daytime high around 32°C in September, and nighttime lows around 22°C. Finish your sightseeing early on the 27th (Tue) so you can drive to Williamsburg.
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Parks · Museums · Outdoors · Nature
Side Trips
Find places to stay Sep 21 — 27:

Williamsburg — 6 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.
Change things up with these side-trips from Williamsburg: The Mariners' Museum & Park (in Newport News) and Smithfield (St. Luke's Historic Church & Museum & Windsor Castle Park). Plan for a day of cool, family-friendly fun on the 30th (Fri) at Busch Gardens Williamsburg. There's lots more to do: contemplate the long history of Colonial Williamsburg, explore the striking landscape of Colonial National Historical Park, take an in-depth tour of Historic Jamestowne, and take a memorable tour with Tours.

To find reviews, where to stay, photos, and more tourist information, go to the Williamsburg road trip app.

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 September, daytime highs in Williamsburg are 34°C, while nighttime lows are 22°C. Wrap up your sightseeing on the 3rd (Mon) to allow time to fly to Abingdon.
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Historic Sites · Parks · Museums · Theme Parks
Side Trips
Find places to stay Sep 27 — Oct 3:

Abingdon — 6 nights

Abingdon is a town in Washington County, Virginia, United States, southwest of Roanoke. Venture out of the city with trips to Wise (High Knob Recreational Area & MountainRose Vineyards), Breaks Interstate Park (in Breaks) and South Holston River Company (in Bristol). There's much more to do: hike along Virginia Creeper National Recreation Trail, admire the striking features of Moss Arts Center, explore the landscape on two wheels at Shuttle Shack, and take an in-depth tour of The Birthplace of Country Music Museum.

To see reviews, photos, and more tourist information, go to the Abingdon trip planner.

Traveling by flight from Williamsburg to Abingdon takes 5 hours. Alternatively, you can drive; or do a combination of bus and taxi. In October, Abingdon is a bit cooler than Williamsburg - with highs of 24°C and lows of 11°C. Finish your sightseeing early on the 9th (Sun) to allow enough time to drive to Mouth of Wilson.
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Parks · Outdoors · Trails · Museums
Side Trips
Find places to stay Oct 3 — 9:

Mouth of Wilson — 1 night

Mouth of Wilson is an unincorporated community, in Grayson County in the U.S. state of Virginia, just north of the North Carolina state line. On the 10th (Mon), take your sightseeing to a higher altitude at Whitetop Mountain and then immerse yourself in nature at Grayson Highlands State Park.

For ratings, other places to visit, where to stay, and other tourist information, you can read our Mouth of Wilson trip maker site.

You can drive from Abingdon to Mouth of Wilson in 1.5 hours. While traveling from Abingdon, expect slightly colder days and about the same nights in Mouth of Wilson, ranging from highs of 20°C to lows of 9°C. Finish your sightseeing early on the 10th (Mon) so you can drive to Floyd.
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Parks · Nature
Find places to stay Oct 9 — 10:

Floyd — 3 nights

Floyd is a town in Floyd County, Virginia, United States. Venture out of the city with trips to Draper Mountain Overlook (in Pulaski), Primland Resort Golf Course (in Meadows of Dan) and Beaver Dam Creek Walking Trail (in Hillsville). There's still lots to do: get in on the family fun at Buffalo Mountain Ziplines, look for all kinds of wild species at Rocky Knob Recreational Area, contemplate the long history of Mabry Mill, and look for gifts at Floyd Country Store.

To find maps, more things to do, photos, and tourist information, refer to the Floyd trip website.

You can drive from Mouth of Wilson to Floyd in 1.5 hours. In October, daytime highs in Floyd are 22°C, while nighttime lows are 7°C. Cap off your sightseeing on the 13th (Thu) early enough to go by car to Bedford.
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Shopping · Wildlife · Outdoors · Parks
Side Trips
Find places to stay Oct 10 — 13:

Bedford — 4 nights

Bedford is an incorporated town and former independent city located within Bedford County in the U.S. state of Virginia. Explore the numerous day-trip ideas around Bedford: Falling Springs Waterfall (in Covington), Smith Mountain Lake (in Moneta) and Booker T. Washington National Monument (in Hardy). There's still lots to do: appreciate the history behind National D-Day Memorial, experience rural life at A.J. Gross & Sons Orchard, bet on your favorite at South Boston Speedway, and take an in-depth tour of Bedford Boys Tribute Center.

To see more things to do, ratings, traveler tips, and more tourist information, read Bedford trip planner.

You can drive from Floyd to Bedford in 1.5 hours. October in Bedford sees daily highs of 24°C and lows of 9°C at night. Cap off your sightseeing on the 17th (Mon) early enough to go by car to Charlottesville.
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Parks · Nature · Historic Sites · Museums
Side Trips
Find places to stay Oct 13 — 17:

Charlottesville — 6 nights

Hoo-Ville

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.
Explore the numerous day-trip ideas around Charlottesville: Natural Bridge (Virginia Safari Park & Natural Bridge State Park), Old Rag Mountain Hike (in Shenandoah National Park) and Orange (James Madison Museum, Central Virginia Wine Tours & Transportation, &more). There's much more to do: admire the natural beauty at Monticello, deepen your understanding at Virginia Military Institute, examine the collection at Camera Heritage Museum, and admire the masterpieces at Kluge-Ruhe Aboriginal Art Collection of the University of Virginia.

To find other places to visit, more things to do, where to stay, and tourist information, read Charlottesville journey maker app.

You can drive from Bedford to Charlottesville in 2 hours. October in Charlottesville sees daily highs of 25°C and lows of 11°C at night. Wrap up your sightseeing on the 23rd (Sun) early enough to drive to Luray.
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Parks · Historic Sites · Nature · Wildlife
Side Trips
Find places to stay Oct 17 — 23:

Luray — 7 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.
Change things up with these side-trips from Luray: Magnolia Vineyards (in Amissville), Shenandoah National Park (Skyline Drive & Hawksbill Mountain) and Moving Meadows Farm (in Culpeper). Spend the 28th (Fri) exploring nature at Shenandoah National Park. Next up on the itinerary: take in breathtaking views at Luray Caverns, get a dose of the wild on Raptor Hill Falconry, take a memorable excursion with Birdsong Pleasure Garden, and stroll through Luray Hawksbill Greenway.

To see where to stay, other places to visit, and more tourist information, use the Luray day trip app.

You can drive from Charlottesville to Luray in 1.5 hours. Another option is to do a combination of bus and taxi. In October, plan for daily highs up to 24°C, and evening lows to 10°C. Wrap up your sightseeing on the 30th (Sun) early enough to travel back home.
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Parks · Nature · Outdoors · Tours
Side Trips
Find places to stay Oct 23 — 30:

Virginia travel guide

4.5
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.
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