7 days in Virginia & Washington DC Itinerary
Created using Inspirock United States trip planner
Start from...
1
Dulles
— 1 day
Drive
2
Washington DC
— 1 night
Fly
3
Charlottesville
— 1 night
Drive
4
Williamsburg
— 1 night
Drive
5
Virginia Beach
Drive
6
Dulles
— 1 night
Drive
End: Chicago
Sat, Oct 7 - Fri, Oct 13
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Dulles — 1 day

On the 7th (Sat), do a tasting at Quattro Goomba's Winery, learn about winemaking at Chrysalis Vineyards at The Ag District, and then do a tasting at Cana Vineyards and Winery.
To see more things to do, ratings, and more tourist information, go to the Dulles day trip planner.
The Route module shows you travel options from your home to Dulles. In October, daily temperatures in Dulles can reach 70°F, while at night they dip to 47°F. Wrap up your sightseeing on the 7th (Sat) early enough to drive to Washington DC.
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To see more things to do, ratings, and more tourist information, go to the Dulles day trip planner.
The Route module shows you travel options from your home to Dulles. In October, daily temperatures in Dulles can reach 70°F, while at night they dip to 47°F. Wrap up your sightseeing on the 7th (Sat) early enough to drive to Washington DC.
Side Trips
Highlights from your trip
Washington DC — 1 night

Start off your visit on the 8th (Sun): take an in-depth tour of United States Holocaust Memorial Museum, admire the masterpieces at National Gallery of Art, appreciate the history behind Washington Monument, then appreciate the history behind Vietnam Veterans Memorial, and finally appreciate the history behind Lincoln Memorial.
To see reviews, photos, maps, and tourist information, go to the Washington DC online travel planner.
Getting from Dulles to Washington DC by car takes about an hour. Other options: drive. Traveling from Dulles in October, you can expect nighttime temperatures to be somewhat warmer in Washington DC, with lows of 54°F. On the 9th (Mon), wrap the sightseeing up by early afternoon so you can fly to Charlottesville.
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To see reviews, photos, maps, and tourist information, go to the Washington DC online travel planner.
Getting from Dulles to Washington DC by car takes about an hour. Other options: drive. Traveling from Dulles in October, you can expect nighttime temperatures to be somewhat warmer in Washington DC, with lows of 54°F. On the 9th (Mon), wrap the sightseeing up by early afternoon so you can fly to Charlottesville.
Highlights from your trip
Charlottesville — 1 night
Hoo-Ville
Kick off your visit on the 9th (Mon): view the masterpieces at C'ville Arts: A Cooperative Gallery and then admire the striking features of University of Virginia.
To find more things to do, ratings, photos, and tourist information, read our Charlottesville trip itinerary builder site.
Traveling by flight from Washington DC to Charlottesville takes 2.5 hours. Alternatively, you can drive; or take a train. Plan for a bit cooler nights when traveling from Washington DC in October since evenings lows in Charlottesville dip to 49°F. Finish your sightseeing early on the 10th (Tue) to allow enough time to drive to Williamsburg.
more
To find more things to do, ratings, photos, and tourist information, read our Charlottesville trip itinerary builder site.
Traveling by flight from Washington DC to Charlottesville takes 2.5 hours. Alternatively, you can drive; or take a train. Plan for a bit cooler nights when traveling from Washington DC in October since evenings lows in Charlottesville dip to 49°F. Finish your sightseeing early on the 10th (Tue) to allow enough time to drive to Williamsburg.
Highlights from your trip
Williamsburg — 1 night

Colonial Capital
Start off your visit on the 11th (Wed): contemplate the long history of Governor's Palace, contemplate the long history of Colonial Williamsburg, then contemplate the long history of Yorktown Battlefield, and finally hike along Tyndall's Point Park.
For where to stay, traveler tips, ratings, and more tourist information, read our Williamsburg road trip planning app.
You can drive from Charlottesville to Williamsburg in 2.5 hours. Alternatively, you can take a bus; or do a combination of bus and train. Traveling from Charlottesville in October, plan for somewhat warmer nights in Williamsburg, with lows around 55°F. Finish up your sightseeing early on the 11th (Wed) so you can go by car to Virginia Beach.
more
For where to stay, traveler tips, ratings, and more tourist information, read our Williamsburg road trip planning app.
You can drive from Charlottesville to Williamsburg in 2.5 hours. Alternatively, you can take a bus; or do a combination of bus and train. Traveling from Charlottesville in October, plan for somewhat warmer nights in Williamsburg, with lows around 55°F. Finish up your sightseeing early on the 11th (Wed) so you can go by car to Virginia Beach.
Side Trips
Highlights from your trip

The Resort City
To find reviews, maps, where to stay, and tourist information, read our Virginia Beach vacation builder website.
Drive from Williamsburg to Virginia Beach in 1.5 hours. Alternatively, you can take a bus; or do a combination of train and bus. In October, daily temperatures in Virginia Beach can reach 74°F, while at night they dip to 56°F. On the 11th (Wed), you're off to Dulles.
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Drive from Williamsburg to Virginia Beach in 1.5 hours. Alternatively, you can take a bus; or do a combination of train and bus. In October, daily temperatures in Virginia Beach can reach 74°F, while at night they dip to 56°F. On the 11th (Wed), you're off to Dulles.
Dulles — 1 night

Start off your visit on the 12th (Thu): tee off at 1757 Golf Club, do a tasting at Greenhill Winery and Vineyards, and then learn about winemaking at Barrel Oak Winery.
For ratings, reviews, other places to visit, and other tourist information, you can read our Dulles trip itinerary tool.
Drive from Virginia Beach to Dulles in 3.5 hours. Traveling from Virginia Beach in October, expect slightly colder with lows of 47°F in Dulles. On the 13th (Fri), wrap the sightseeing up by early afternoon so you can drive back home.
more
For ratings, reviews, other places to visit, and other tourist information, you can read our Dulles trip itinerary tool.
Drive from Virginia Beach to Dulles in 3.5 hours. Traveling from Virginia Beach in October, expect slightly colder with lows of 47°F in Dulles. On the 13th (Fri), wrap the sightseeing up by early afternoon so you can drive back home.
Side Trips
Highlights from your trip
Virginia travel guide
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.