30 days in Virginia Itinerary

30 days in Virginia Itinerary

Created using Inspirock Virginia trip itinerary planner

Make it your trip
Train to Airport Terminal B, Fly to Chincoteague Island
1
Chincoteague Island
— 2 nights
Drive
2
Virginia Beach
— 4 nights
Drive
3
Williamsburg
— 4 nights
Drive
4
Charlottesville
— 4 nights
Drive
5
Bedford
— 2 nights
Drive
6
Damascus
— 2 nights
Drive
7
Luray
— 4 nights
Drive
8
Winchester
— 3 nights
Drive
9
Arlington
— 4 nights
Fly

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Chincoteague Island

— 2 nights
Famous for a wild breed of horses--Chincoteague Ponies--Chincoteague Island embraces the mystery of some of North America’s oldest inhabitants.
Spend the 2nd (Thu) exploring nature at Chincoteague National Wildlife Refuge. Next up on the itinerary: get up close to creatures of the deep with Captain Dan's Around the Island Tours, make a trip to Chincoteague Cultural Alliance, explore the landscape on two wheels at Bike Depot, and get outside with Donald J. Leonard.

To find reviews, maps, where to stay, and tourist information, go to the Chincoteague Island day trip app.

New York City to Chincoteague Island is an approximately 5-hour combination of train and flight. You can also drive; or do a combination of train and bus. In September, daily temperatures in Chincoteague Island can reach 80°F, while at night they dip to 64°F. Finish your sightseeing early on the 3rd (Fri) to allow enough time to drive to Virginia Beach.

Things to do in Chincoteague Island

Wildlife · Parks · Nature · Outdoors

Side Trip

Virginia Beach

— 4 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.
Change things up with these side-trips from Virginia Beach: Norfolk (Hermitage Museum and Gardens & Weyanoke Bird and Wildflower Sanctuary). And it doesn't end there: take in the waterfront at Virginia Beach Boardwalk, step aboard Battleship Wisconsin at Nauticus, don't miss a visit to Cape Henry Lighthouse, and enjoy the sand and surf at Sandbridge Beach.

To see photos, maps, more things to do, and other tourist information, read our Virginia Beach trip tool.

Drive from Chincoteague Island to Virginia Beach in 2.5 hours. Alternatively, you can take a bus; or take a bus. September in Virginia Beach sees daily highs of 81°F and lows of 67°F at night. Finish up your sightseeing early on the 7th (Tue) so you can go by car to Williamsburg.

Things to do in Virginia Beach

Parks · Outdoors · Museums · Beaches

Side Trip

Williamsburg

— 4 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.
Change things up with these side-trips from Williamsburg: St. Luke's Historic Church & Museum (in Smithfield) and The Mariners' Museum & Park (in Newport News). The adventure continues: get engrossed in the history at Colonial Williamsburg, steep yourself in history at Historic Jamestowne, find something for the whole family at Busch Gardens Williamsburg, and stop by Quirks of Art.

To see other places to visit, photos, reviews, and other tourist information, go to the Williamsburg itinerary planning tool.

Traveling by car from Virginia Beach to Williamsburg takes 1.5 hours. Alternatively, you can take a bus; or do a combination of bus and train. September in Williamsburg sees daily highs of 84°F and lows of 66°F at night. Wrap up your sightseeing on the 11th (Sat) early enough to drive to Charlottesville.

Things to do in Williamsburg

Historic Sites · Museums · Theme Parks · Parks

Side Trips

Charlottesville

— 4 nights

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.
Explore Charlottesville's surroundings by going to Virginia Military Institute (in Lexington), James Madison's Montpelier (in Montpelier Station) and Old Rag Mountain Hike (in Shenandoah National Park). And it doesn't end there: steep yourself in history at Monticello, experience rural life at Seamans’ Orchard, explore the striking landscape of Appomattox Court House National Historical Park, and take in the dramatic natural features at Natural Bridge State Park.

To see where to stay, maps, reviews, and other tourist information, read our Charlottesville trip itinerary planning tool.

You can drive from Williamsburg to Charlottesville in 2.5 hours. Alternatively, you can take a bus; or do a combination of train and bus. Traveling from Williamsburg in September, you can expect nighttime temperatures to be slightly colder in Charlottesville, with lows of 60°F. Finish your sightseeing early on the 15th (Wed) so you can travel to Bedford.

Things to do in Charlottesville

Historic Sites · Parks · Nature · Trails

Side Trips

Bedford

— 2 nights
Bedford is an incorporated town and former independent city located within Bedford County in the U.S. state of Virginia. Start off your visit on the 16th (Thu): contemplate the long history of Booker T. Washington National Monument, contemplate the waterfront views at Smith Mountain Lake, and then get to know the fascinating history of Historic Centertown Bedford. On your second day here, admire the landmark architecture of Thomas Jefferson's Poplar Forest, then examine the collection at Bedford Museum & Genealogical Library, and then appreciate the history behind National D-Day Memorial.

To find traveler tips, maps, other places to visit, and more tourist information, use the Bedford online sightseeing planner.

Traveling by car from Charlottesville to Bedford takes 2 hours. In September, plan for daily highs up to 79°F, and evening lows to 59°F. Finish your sightseeing early on the 17th (Fri) so you can travel to Damascus.

Things to do in Bedford

Historic Sites · Neighborhoods · Museums · Nature

Side Trips

Damascus

— 2 nights
Damascus is a town in Washington County, Virginia, United States. On the 18th (Sat), hike along Appalachian Trail, grab your bike and head to Adventure Damascus, and then stroll through Virginia Creeper National Recreation Trail. Get ready for a full day of sightseeing on the next day: take in the awesome beauty at Whitetop Mountain, admire the majestic nature at Grayson Highlands State Park, and then admire the majestic nature at Hungry Mother State Park.

To find maps, reviews, other places to visit, and more tourist information, you can read our Damascus trip builder app.

You can drive from Bedford to Damascus in 3 hours. Expect a daytime high around 79°F in September, and nighttime lows around 59°F. Wrap up your sightseeing on the 19th (Sun) early enough to travel to Luray.

Things to do in Damascus

Parks · Trails · Outdoors · Nature

Side Trips

Luray

— 4 nights

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.
Explore the numerous day-trip ideas around Luray: A Dream Come True Playground (in Harrisonburg), SoLace Studios Fine Handcrafts (in Elkton) and Skyline Drive (in Shenandoah National Park). And it doesn't end there: take in breathtaking views at Luray Caverns, tour the pleasant surroundings at Luray Hawksbill Greenway, admire the natural beauty at Birdsong Pleasure Garden, and see the interesting displays at The Car and Carriage Caravan Museum.

To see other places to visit, where to stay, photos, and tourist information, read Luray tour itinerary builder site.

You can drive from Damascus to Luray in 4.5 hours. Another option is to do a combination of car and flight. Expect a daytime high around 79°F in September, and nighttime lows around 57°F. Finish your sightseeing early on the 23rd (Thu) to allow enough time to drive to Winchester.

Things to do in Luray

Parks · Outdoors · Nature · Trails

Side Trips

Winchester

— 3 nights
Winchester is an independent city located in the northwestern portion of the Commonwealth of Virginia. Venture out of the city with trips to Purcellville (Blue Ridge Center for Environmental Stewardship, Catoctin Creek Distillery, &more), National Sporting Library & Museum (in Middleburg) and Sky Meadows State Park (in Delaplane). And it doesn't end there: get a taste of life in the country at Rocking S Ranch, steep yourself in history at Patsy Cline Historic House, get engrossed in the history at Virginia Museum of Veiled History, and admire the masterpieces at Museum of the Shenandoah Valley.

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

You can drive from Luray to Winchester in 1.5 hours. In September, daily temperatures in Winchester can reach 78°F, while at night they dip to 56°F. Finish your sightseeing early on the 26th (Sun) so you can drive to Arlington.

Things to do in Winchester

Parks · Historic Sites · Museums · Trails

Side Trips

Arlington

— 4 nights

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.
You'll find plenty of places to visit near Arlington: George Washington's Mount Vernon (in Mount Vernon), Steven F. Udvar-Hazy Center (in Chantilly) and National Museum of the Marine Corps (in Triangle). There's still lots to do: stroll the grounds of Arlington National Cemetery, make a trip to John F. Kennedy Grave Site, steep yourself in history at Little Library, and visit Old Town.

To see ratings, more things to do, traveler tips, and tourist information, you can read our Arlington route planner.

Traveling by car from Winchester to Arlington takes 1.5 hours. Alternatively, you can do a combination of taxi and bus; or do a combination of taxi, train, and subway. Traveling from Winchester in September, Arlington is a bit warmer at night with lows of 65°F. Wrap up your sightseeing on the 30th (Thu) early enough to fly back home.

Things to do in Arlington

Historic Sites · Parks · Museums · Trails

Side Trips

Virginia travel guide

4.6
History Museums · Wineries & Vineyards · Historic Sites
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.