8 days in Virginia Itinerary

8 days in Virginia Itinerary

Created using Inspirock Virginia trip itinerary builder
Make it your trip
Shenandoah National Park
— 2 nights
— 1 night
Chincoteague Island
— 1 night
Virginia Beach
— 2 nights


Shenandoah National Park — 2 nights

Shenandoah National Park showcases a particularly scenic section of Virginia's Blue Ridge Mountains.
Kick off your visit on the 18th (Sun): trek along Jones Run Falls Trailhead, then learn about winemaking at Moss Vineyards, and then learn about winemaking at Brix and Columns Vineyards. Here are some ideas for day two: get a dose of the wild on Raptor Hill Falconry, then head outdoors with Shenandoah River Adventures, and then indulge in some personalized pampering at The Spa at Massanutten.

For ratings, where to stay, and tourist information, you can read our Shenandoah National Park online road trip planner.

Des Moines to Shenandoah National Park is an approximately 7-hour flight. You can also drive; or do a combination of bus, train, and taxi. Traveling from Des Moines to Shenandoah National Park, you'll lose 1 hour due to the time zone difference. Plan for a bit warmer temperatures traveling from Des Moines in December, with highs in Shenandoah National Park at 52°F and lows at 34°F. Finish your sightseeing early on the 20th (Tue) to allow enough time to drive to Charlottesville.
Outdoors · Wineries · Tours · Wildlife
Side Trips

Charlottesville — 1 night


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 20th (Tue): learn about winemaking at Valley Road Vineyards. On your second day here, trek along Saunders-Monticello Trail, identify plant and animal life at Ivy Creek Natural Area, and then do a tasting at Barren Ridge Vineyards.

For reviews, photos, more things to do, and tourist information, refer to the Charlottesville road trip tool.

You can drive from Shenandoah National Park to Charlottesville in 1.5 hours. In December, daily temperatures in Charlottesville can reach 52°F, while at night they dip to 34°F. Finish your sightseeing early on the 21st (Wed) so you can drive to Chincoteague Island.
Parks · Wineries · Outdoors · Wildlife
Side Trips

Chincoteague Island — 1 night

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 22nd (Thu): explore the wealth of natural beauty at Chincoteague National Wildlife Refuge.

For more things to do, photos, ratings, and other tourist information, read Chincoteague Island sightseeing planner.

Traveling by car from Charlottesville to Chincoteague Island takes 5 hours. Alternatively, you can do a combination of flight and taxi; or take a bus. Expect a daytime high around 53°F in December, and nighttime lows around 36°F. Finish up your sightseeing early on the 23rd (Fri) so you can go by car to Virginia Beach.
Nature · Wildlife · Parks
Highlights from your trip

Virginia Beach — 2 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.
Your day by day itinerary now includes Virginia Zoo, Virginia Aquarium & Marine Science Center and The Adventure Park at Virginia Aquarium. Take a break from the city and head to Sandbridge Beach and Adrenaline & Extreme Tours. Change things up with a short trip to Weyanoke Bird and Wildflower Sanctuary in Norfolk (about 36 minutes away). There's still lots to do: immerse yourself in nature at First Landing State Park.

For ratings, traveler tips, and tourist information, read Virginia Beach itinerary planner.

Drive from Chincoteague Island to Virginia Beach in 2.5 hours. Alternatively, you can take a bus; or take a bus. Expect a daytime high around 56°F in December, and nighttime lows around 39°F. Finish your sightseeing early on the 25th (Sun) so you can fly back home.
Parks · Outdoors · Tours · Wildlife
Side Trip

Virginia travel guide

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.