5 days in Virginia Itinerary

5 days in Virginia Itinerary

Created using Inspirock Virginia visit planner

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Plan created by another user. Make it yours
Fly
1
Chincoteague Island
— 1 day
Drive
2
Virginia Beach
— 1 night
Drive
3
Charlottesville
— 2 nights
Drive
4
Appomattox
— 1 night
Drive

S M T W T F S
27
28
29
30
1
2
3

1
day
Chincoteague Island

Famous for a wild breed of horses--Chincoteague Ponies--Chincoteague Island embraces the mystery of some of North America’s oldest inhabitants.
Start off your visit on the 29th (Tue): get outside with Donald J. Leonard and then get up close to creatures of the deep with Captain Dan's Around the Island Tours.

To find more things to do, where to stay, other places to visit, and other tourist information, read Chincoteague Island road trip planner.

Charlotte to Chincoteague Island is an approximately 4.5-hour flight. You can also drive; or take a bus. September in Chincoteague Island sees daily highs of 80°F and lows of 64°F at night. Finish up your sightseeing early on the 29th (Tue) so you can go by car to Virginia Beach.

Things to do in Chincoteague Island

Outdoors · Wildlife · Tours
Highlights from your trip

1
night
Virginia Beach

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.
Kick off your visit on the 30th (Wed): take a pleasant ride with a tour on horseback, then kick back and relax at Sandbridge Beach, then get the adrenaline pumping with iFLY Va Beach Indoor Skydiving, and finally admire the majestic nature at First Landing State Park.

To find photos, where to stay, traveler tips, and tourist information, read our Virginia Beach online tour planner.

Traveling by car from Chincoteague Island to Virginia Beach takes 2.5 hours. Alternatively, you can take a bus; or take a bus. In September, daily temperatures in Virginia Beach can reach 81°F, while at night they dip to 67°F. Wrap up your sightseeing on the 30th (Wed) early enough to drive to Charlottesville.

Things to do in Virginia Beach

Outdoors · Parks · Tours · Wildlife

2
nights
Charlottesville

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.
Start off your visit on the 1st (Thu): contemplate the long history of James Monroe's Highland, then steep yourself in history at James Madison's Montpelier, and then hike along Saunders-Monticello Trail. Keep things going the next day: do a tasting at King Family Vineyards and then do a tasting at Veritas Vineyard & Winery.

Inspirock's itinerary builder makes planning a Charlottesville trip simple and quick.

Getting from Virginia Beach to Charlottesville by car takes about 3 hours. Other options: fly; or take a bus. Traveling from Virginia Beach in September, you can expect nighttime temperatures to be a bit cooler in Charlottesville, with lows of 60°F. Wrap up your sightseeing on the 2nd (Fri) to allow time to drive to Appomattox.

Things to do in Charlottesville

Wineries · Shopping · Historic Sites · Outdoors

Side Trips

1
night
Appomattox

Appomattox is a town in Appomattox County, Virginia, United States. Kick off your visit on the 3rd (Sat): contemplate the long history of McLean House, explore the wealth of natural beauty at Appomattox Court House National Historical Park, and then learn about all things military at The American Civil War Museum - Appomattox.

For other places to visit, reviews, and more tourist information, refer to the Appomattox trip planning site.

Traveling by car from Charlottesville to Appomattox takes 1.5 hours. In October, daytime highs in Appomattox are 70°F, while nighttime lows are 47°F. Finish up your sightseeing early on the 3rd (Sat) so you can travel back home.

Things to do in Appomattox

Historic Sites · Nature · Parks · Museums

Virginia travel guide

4.6
Historic Sites · Wineries & Vineyards · Specialty Museums
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.