16 days in Virginia Itinerary

16 days in Virginia Itinerary

Created using Inspirock Virginia trip itinerary planner

Plan created by another user. Make it yours
Fly
1
Arlington
— 2 nights
Drive
2
Winchester
— 1 night
Drive
3
Luray
— 1 night
Drive
4
Charlottesville
— 2 nights
Drive
5
Bedford
— 1 night
Drive
6
Williamsburg
— 3 nights
Drive
7
Virginia Beach
— 3 nights
Drive
8
Chincoteague Island
— 2 nights
Fly

S M T W T F S
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1
2

2
nights
Arlington

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.
Explore Arlington's surroundings by going to Steven F. Udvar-Hazy Center (in Chantilly) and George Washington's Mount Vernon (in Mount Vernon). The adventure continues: explore the different monuments and memorials at Arlington National Cemetery, tour the pleasant surroundings at Mount Vernon Trail, pause for some photo ops at Air Force Memorial, and take a stroll through Old Town.

Start your trip to Arlington by creating a personalized itinerary on Inspirock.

San Diego to Arlington is an approximately 7-hour flight. You can also drive; or do a combination of train and subway. The time zone difference moving from Pacific Standard Time (PST) to Eastern Standard Time (EST) is 3 hours. In September, daily temperatures in Arlington can reach 82°F, while at night they dip to 65°F. Finish your sightseeing early on the 15th (Wed) so you can drive to Winchester.

Things to do in Arlington

Historic Sites · Museums · Trails · Parks

Side Trips

1
night
Winchester

Winchester is an independent city located in the northwestern portion of the Commonwealth of Virginia. Kick off your visit on the 16th (Thu): contemplate the long history of Belle Grove Plantation, stop by Marker-Miller Orchards, then admire the masterpieces at Museum of the Shenandoah Valley, and finally wander the wide-open spaces of Rocking S Ranch.

To find where to stay, ratings, more things to do, and other tourist information, go to the Winchester trip builder site.

You can drive from Arlington to Winchester in 1.5 hours. Alternatively, you can do a combination of bus and taxi; or do a combination of subway, train, and taxi. Traveling from Arlington in September, expect a bit cooler with lows of 56°F in Winchester. Wrap up your sightseeing on the 16th (Thu) early enough to drive to Luray.

Things to do in Winchester

Historic Sites · Museums · Shopping

Side Trip

1
night
Luray

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 17th (Fri): brush up on your knowledge of spirits at Copper Fox Distillery, then hike along Stony Man Mountain Overlook, then take a pleasant ride with Jordan Hollow Stables, and finally explore the fascinating underground world of Luray Caverns.

To find reviews, maps, where to stay, and more tourist information, you can read our Luray trip itinerary tool.

Getting from Winchester to Luray by car takes about 1.5 hours. In September, daytime highs in Luray are 79°F, while nighttime lows are 57°F. Finish up your sightseeing early on the 17th (Fri) so you can go by car to Charlottesville.

Things to do in Luray

Parks · Outdoors · Nature · Trails

Side Trips

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.
Kick off your visit on the 18th (Sat): relax in the rural setting at Carter Mountain Orchard and then gain some tasty knowledge on Norm's Executive Transportation. Keep things going the next day: admire the natural beauty at Monticello, then contemplate the long history of James Monroe's Highland, and then test your problem-solving skills at Crack The Code Escape Room.

To see where to stay, more things to do, traveler tips, and other tourist information, you can read our Charlottesville itinerary maker site.

Traveling by car from Luray to Charlottesville takes 1.5 hours. Alternatively, you can do a combination of taxi and bus. In September in Charlottesville, expect temperatures between 80°F during the day and 60°F at night. Finish your sightseeing early on the 19th (Sun) so you can travel to Bedford.

Things to do in Charlottesville

Historic Sites · Breweries & Distilleries · Transportation · Parks

Side Trip

1
night
Bedford

Bedford is an incorporated town and former independent city located within Bedford County in the U.S. On the 20th (Mon), admire the striking features of Thomas Jefferson's Poplar Forest, see the interesting displays at Bedford Museum & Genealogical Library, and then pause for some photo ops at National D-Day Memorial.

For other places to visit, where to stay, maps, and tourist information, you can read our Bedford driving holiday planning tool.

You can drive from Charlottesville to Bedford in 2 hours. In September in Bedford, expect temperatures between 79°F during the day and 59°F at night. Finish up your sightseeing early on the 20th (Mon) so you can travel to Williamsburg.

Things to do in Bedford

Museums

Side Trip

3
nights
Williamsburg

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.
Venture out of the city with trips to The Mariners' Museum & Park (in Newport News) and St. Luke's Historic Church & Museum (in Smithfield). And it doesn't end there: steep yourself in history at Colonial Williamsburg, stop by Quirks of Art, trek along Tyndall's Point Park, and step aboard Jamestown Settlement.

For ratings, where to stay, more things to do, and other tourist information, refer to the Williamsburg trip itinerary maker tool.

Traveling by car from Bedford to Williamsburg takes 3.5 hours. Expect a bit warmer evenings in Williamsburg when traveling from Bedford in September, with lows around 66°F. Finish your sightseeing early on the 23rd (Thu) to allow enough time to drive to Virginia Beach.

Things to do in Williamsburg

Historic Sites · Museums · Parks · Trails

Side Trips

3
nights
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.
Virginia Beach is known for beaches, zoos & aquariums, and adventure. Your plan includes some of its best attractions: take a leisurely stroll along Virginia Beach Boardwalk, brush up on your military savvy at Military Aviation Museum, immerse yourself in nature at First Landing State Park, and kick back and relax at Sandbridge Beach.

To find other places to visit, ratings, and tourist information, use the Virginia Beach trip app.

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 September, daily temperatures in Virginia Beach can reach 81°F, while at night they dip to 67°F. Finish your sightseeing early on the 26th (Sun) so you can drive to Chincoteague Island.

Things to do in Virginia Beach

Outdoors · Parks · Beaches · Tours

Side Trip

2
nights
Chincoteague Island

Famous for a wild breed of horses--Chincoteague Ponies--Chincoteague Island embraces the mystery of some of North America’s oldest inhabitants.
On the 27th (Mon), look for all kinds of wild species at Chincoteague National Wildlife Refuge. On the 28th (Tue), you'll have a packed day of sightseeing: look for gifts at Wine Cheese & More, get up close to creatures of the deep with Captain Dan's Around the Island Tours, and then get outside with Donald J. Leonard.

For traveler tips, ratings, photos, and tourist information, go to the Chincoteague Island online trip maker.

You can drive from Virginia Beach to Chincoteague Island in 2.5 hours. Other options are to take a bus; or take a bus. Expect a daytime high around 80°F in September, and nighttime lows around 64°F. Cap off your sightseeing on the 28th (Tue) early enough to travel back home.

Things to do in Chincoteague Island

Wildlife · Parks · Nature · Outdoors

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.