6 days in Virginia Itinerary
6 days in Virginia Itinerary
Created using Inspirock Virginia trip planner
Route & dates
6 days in Virginia Itinerary
Start: Chicago
Fly:
4h 15min
1
Virginia Beach
— 1 night
Drive:
1h 15min
2
Williamsburg
— 2 nights
Drive:
3h 15min
3
Luray
— 1 night
Drive:
1h 45min
4
Arlington
— 1 night
Fly:
3h 30min
End: Chicago
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1
night
Virginia Beach
1
night

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.Start off your visit on the 17th (Wed): enjoy the sand and surf at Virginia Beach.
For traveler tips, maps, photos, and more tourist information, read our Virginia Beach trip planning tool .
Chicago to Virginia Beach is an approximately 4.5-hour combination of flight and taxi. You can also drive; or do a combination of train and tram. The time zone difference when traveling from Chicago to Virginia Beach is 1 hour. Expect somewhat warmer temperatures when traveling from Chicago in October; daily highs in Virginia Beach reach 74°F and lows reach 56°F. Finish your sightseeing early on the 18th (Thu) to allow enough time to drive to Williamsburg.
Things to do in Virginia Beach
Highlights from your plan

Virginia Beach
3:00pm, Wed Oct 17

Sandbridge Beach
12:00pm, Thu Oct 18

Virginia Beach Boardwalk
4:00pm, Thu Oct 18
2
nights
Williamsburg
2
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.Kick off your visit on the 19th (Fri): take an in-depth tour of Colonial Williamsburg, steep yourself in history at Historic Jamestowne, and then steep yourself in history at Jamestown Settlement. Get ready for a full day of sightseeing on the 20th (Sat): find something for the whole family at Busch Gardens Williamsburg.
For maps, ratings, where to stay, and tourist information, use the Williamsburg trip planner.
Getting from Virginia Beach to Williamsburg by car takes about 1.5 hours. Other options: take a bus. October in Williamsburg sees daily highs of 75°F and lows of 55°F at night. Finish up your sightseeing early on the 20th (Sat) so you can go by car to Luray.
Things to do in Williamsburg
Highlights from your plan

Colonial Williamsburg
10:00am, Fri Oct 19

Busch Gardens Williamsburg
10:00am, Sat Oct 20

Historic Jamestowne
2:30pm, Fri Oct 19
1
night
Luray
1
night

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.Start off your visit on the 21st (Sun): take a memorable drive along Skyline Drive and then take in breathtaking views at Luray Caverns.
To see traveler tips, maps, and more tourist information, you can read our Luray day trip planning website .
Drive from Williamsburg to Luray in 3.5 hours. Alternatively, you can do a combination of train and car; or do a combination of bus, flight, and car. Expect slightly colder temperatures when traveling from Williamsburg in October; daily highs in Luray reach 70°F and lows reach 48°F. Wrap up your sightseeing on the 21st (Sun) early enough to drive to Arlington.
Things to do in Luray
Side Trip
Skyline Drive
Highlights from your plan

Luray Caverns
2:30pm, Sun Oct 21

Skyline Drive
10:00am, Sun Oct 21
1
night
Arlington
1
night

National History, Local Flavor
Located just across the Potomac River from Washington, D.C., the county of Arlington blends big city and sprawling suburban environments.Kick off your visit on the 22nd (Mon): appreciate the extensive heritage of Tomb of the Unknowns, contemplate the long history of Old Town, and then explore the different monuments and memorials at Arlington National Cemetery.
To find maps, ratings, more things to do, and other tourist information, read Arlington online itinerary builder .
You can drive from Luray to Arlington in 2 hours. Alternatively, you can do a combination of taxi, bus, and subway; or do a combination of taxi, flight, bus, and subway. Traveling from Luray in October, expect somewhat warmer with lows of 54°F in Arlington. Cap off your sightseeing on the 22nd (Mon) early enough to travel back home.
Things to do in Arlington
Side Trip
Old Town
Highlights from your plan

Arlington National Cemetery
3:00pm, Mon Oct 22

Old Town
12:30pm, Mon Oct 22

Tomb of the Unknowns
10:00am, Mon Oct 22
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