6 days in Virginia Itinerary

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.

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.

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.

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.