14 days in Virginia Itinerary

14 days in Virginia Itinerary

Created using Inspirock Virginia holiday planner
Make it your trip
Fly
1
Williamsburg
— 2 nights
Drive
2
Virginia Beach
— 3 nights
Drive
3
Chincoteague Island
— 2 nights
Drive
4
Fredericksburg
— 2 nights
Drive
5
Charlottesville
— 2 nights
Drive
6
Luray
— 2 nights
Fly

S M T W T F S
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Williamsburg — 2 nights

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.
Satisfy your inner culture vulture at American Revolution Museum at Yorktown and Public Hospital Museum. Museum-lovers will appreciate Colonial Williamsburg and Abby Aldrich Rockefeller Folk Art Museum. There's lots more to do: pause for some serene contemplation at Bruton Parish Episcopal Church, get outside with Outdoor Activities, get engrossed in the history at Historic Jamestowne, and get thoroughly spooked out with a ghost and vampire tour.

For photos, other places to visit, ratings, and tourist information, you can read our Williamsburg trip planner.

Chicago to Williamsburg is an approximately 3.5-hour flight. You can also drive; or take a bus. The time zone difference moving from Central Standard Time to Eastern Standard Time is 1 hour. While traveling from Chicago, expect a bit warmer days and about the same nights in Williamsburg, ranging from highs of 89°F to lows of 70°F. Wrap up your sightseeing on the 15th (Tue) to allow time to drive to Virginia Beach.
Historic Sites · Museums · Tours · Outdoors
Side Trip

Virginia Beach — 3 nights

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.
Do some cultural sightseeing at Military Aviation Museum and Nauticus. You'll discover tucked-away gems like Chrysler Museum of Art and Casemate Museum at Fort Monroe. There's lots more to do: glide through the air with a parasailing or paragliding tour, brush up on your knowledge of spirits at Tarnished Truth Distilling Company, and stroll through Sandbridge Beach.

To find reviews, maps, and more tourist information, use the Virginia Beach trip planner.

You can drive from Williamsburg to Virginia Beach in 1.5 hours. Other options are to take a bus; or do a combination of train and bus. Expect a daytime high around 86°F in August, and nighttime lows around 72°F. Finish your sightseeing early on the 18th (Fri) so you can drive to Chincoteague Island.
Museums · Outdoors · Tours · Beaches
Side Trips

Chincoteague Island — 2 nights

Famous for a wild breed of horses--Chincoteague Ponies--Chincoteague Island embraces the mystery of some of North America’s oldest inhabitants.
On the 19th (Sat), grab your bike and head to Bike Depot, then take an in-depth tour of Museum of Chincoteague, and then take a tour by water with Boat Tours & Water Sports. On the 20th (Sun), you'll have a packed day of sightseeing: tour the pleasant surroundings at Chincoteague National Wildlife Refuge.

To see maps, ratings, traveler tips, and other tourist information, use the Chincoteague Island trip planning tool.

Getting from Virginia Beach to Chincoteague Island by car takes about 2.5 hours. Other options: take a bus; or take a bus. Expect a daytime high around 84°F in August, and nighttime lows around 68°F. Cap off your sightseeing on the 20th (Sun) early enough to go by car to Fredericksburg.
Parks · Nature · Wildlife · Outdoors

Fredericksburg — 2 nights

Fredericksburg is an independent city located in the Commonwealth of Virginia in the Eastern United States. On the 21st (Mon), take in the history at Fredericksburg & Spotsylvania National Military Park, take an in-depth tour of Hugh Mercer Apothecary Shop, then get engrossed in the history at The Rising Sun Tavern, and finally appreciate the extensive heritage of Old Town. On the 22nd (Tue), you'll have a packed day of sightseeing: contemplate the long history of Chatham Manor and then brush up on your military savvy at National Museum of the Marine Corps.

For where to stay, reviews, more things to do, and tourist information, read our Fredericksburg trip itinerary builder tool.

Traveling by car from Chincoteague Island to Fredericksburg takes 4.5 hours. Alternatively, you can do a combination of bus and flight; or do a combination of bus and train. August in Fredericksburg sees daily highs of 85°F and lows of 66°F at night. Cap off your sightseeing on the 22nd (Tue) early enough to go by car to Charlottesville.
Historic Sites · Museums
Side Trip

Charlottesville — 2 nights

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.
Kick off your visit on the 23rd (Wed): contemplate the long history of Woodrow Wilson Presidential Library and Museum and then get engrossed in the history at Frontier Culture Museum. On your second day here, contemplate the long history of James Madison's Montpelier and then contemplate the long history of James Monroe's Highland.

To see other places to visit, where to stay, reviews, and more tourist information, use the Charlottesville trip tool.

Traveling by car from Fredericksburg to Charlottesville takes 2 hours. Alternatively, you can take a bus; or take a train. August in Charlottesville sees daily highs of 84°F and lows of 65°F at night. Finish your sightseeing early on the 24th (Thu) so you can drive to Luray.
Historic Sites · Museums
Side Trips

Luray — 2 nights

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.
On the 25th (Fri), explore the fascinating underground world of Shenandoah Caverns, then explore the fascinating underground world of Luray Caverns, and then take an in-depth tour of The Car and Carriage Caravan Museum. Keep things going the next day: kick your exploration up a notch at some of the top local zipline courses and adventure parks, then hike along Stony Man Mountain Overlook, and then take in the dramatic scenery at Dark Hollow Falls.

Plan my trip to Luray with suggested itineraries provided by Inspirock.

Traveling by car from Charlottesville to Luray takes 1.5 hours. Alternatively, you can do a combination of bus and taxi. In August, plan for daily highs up to 83°F, and evening lows to 63°F. Finish your sightseeing early on the 26th (Sat) to allow enough time to fly back home.
Parks · Nature · Outdoors · Museums
Side Trips

Virginia travel guide

4.6
History Museums · Wineries & Vineyards · Historic Sites
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.