41 days in Virginia Itinerary

41 days in Virginia Itinerary

Created using Inspirock Virginia vacation planner
Make it your trip
Fly
1
Winchester
— 3 nights
Drive
2
Luray
— 5 nights
Drive
3
Arlington
— 5 nights
Drive
4
Chincoteague Island
— 4 nights
Drive
5
Virginia Beach
— 5 nights
Drive
6
Williamsburg
— 5 nights
Drive
7
Charlottesville
— 5 nights
Drive
8
Bedford
— 3 nights
Drive
9
Abingdon
— 5 nights
Drive to Asheville, Fly to Fresno

S M T W T F S
18
19
20
21
22
23
24
25
26
27
28
29
30
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
1
2
3
4
5

Winchester — 3 nights

Winchester is an independent city located in the northwestern portion of the Commonwealth of Virginia. Get out of town with these interesting Winchester side-trips: Sky Meadows State Park (in Delaplane) and Purcellville (The Washington & Old Dominion Trail & Catoctin Creek Distillery). There's much more to do: wander the wide-open spaces of Rocking S Ranch, see the interesting displays at Stonewall Jackson's Headquarters, steep yourself in history at Belle Grove Plantation, and stop by Marker-Miller Orchards.

To plan Winchester vacation without wasting time, ask Inspirock to design an itinerary.

Fresno to Winchester is an approximately 8-hour flight. You can also drive; or do a combination of train, bus, and taxi. The time zone difference moving from Pacific Standard Time (PST) to Eastern Standard Time (EST) is 3 hours. Traveling from Fresno in September, expect Winchester to be a bit cooler, temps between 78°F and 56°F. Wrap up your sightseeing on the 23rd (Fri) early enough to drive to Luray.
Museums · Parks · Shopping · Nature
Side Trips

Luray — 5 nights

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: Shenandoah National Park (Hawksbill Mountain & Skyline Drive), Mt. Crawford Creamery (in Mount Crawford) and SoLace Studios Fine Handcrafts (in Elkton). There's much more to do: explore the fascinating underground world of Luray Caverns, take an in-depth tour of The Car and Carriage Caravan Museum, scramble along the landscape with a canyoning and rapelling tour, and stroll through Birdsong Pleasure Garden.

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

Drive from Winchester to Luray in 1.5 hours. In September, daily temperatures in Luray can reach 79°F, while at night they dip to 57°F. Finish your sightseeing early on the 28th (Wed) to allow enough time to drive to Arlington.
Parks · Outdoors · Nature · Trails
Side Trips

Arlington — 5 nights

Located just across the Potomac River from Washington, D.C., the county of Arlington blends big city and sprawling suburban environments.
Explore the numerous day-trip ideas around Arlington: National Museum of the Marine Corps (in Triangle), Manassas National Battlefield Park (in Manassas) and George Washington's Mount Vernon (in Mount Vernon). The adventure continues: stroll the grounds of Arlington National Cemetery, wander the streets of Old Town, appreciate the history behind Pentagon Memorial, and see the interesting displays at Steven F. Udvar-Hazy Center.

To see photos, maps, traveler tips, and other tourist information, go to the Arlington trip planning app.

You can drive from Luray to Arlington in 2 hours. Alternatively, you can fly; or do a combination of taxi and bus. Traveling from Luray in September, plan for somewhat warmer nights in Arlington, with lows around 65°F. Finish your sightseeing early on the 3rd (Mon) so you can drive to Chincoteague Island.
Historic Sites · Museums · Trails · Parks
Side Trips

Chincoteague Island — 4 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 4th (Tue) exploring nature at Chincoteague National Wildlife Refuge. There's still lots to do: get up close to creatures of the deep with a dolphin and whale watching tour, get engrossed in the history at Museum of Chincoteague, look for gifts at MamerSass, and make a trip to Chincoteague Cultural Alliance.

To see reviews, more things to do, traveler tips, and more tourist information, go to the Chincoteague Island trip itinerary app.

Traveling by car from Arlington to Chincoteague Island takes 4 hours. Alternatively, you can do a combination of flight and bus; or do a combination of subway, train, bus, and taxi. In October, daytime highs in Chincoteague Island are 71°F, while nighttime lows are 54°F. Finish your sightseeing early on the 7th (Fri) so you can drive to Virginia Beach.
Wildlife · Parks · Nature · Outdoors
Side Trip

Virginia Beach — 5 nights

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.
Explore Virginia Beach's surroundings by going to Richmond (Capitol Square Park & Virginia Capitol Building). And it doesn't end there: take a leisurely stroll along Virginia Beach Boardwalk, brush up on your knowledge of spirits at Tarnished Truth Distilling Company, get a new perspective on things with Boat Tours & Water Sports, and stroll through Virginia Aquarium & Marine Science Center.

For traveler tips, photos, other places to visit, and other tourist information, read our Virginia Beach trip app.

Getting from Chincoteague Island to Virginia Beach by car takes about 2.5 hours. Other options: take a bus; or take a bus. In October, daily temperatures in Virginia Beach can reach 74°F, while at night they dip to 56°F. Wrap up your sightseeing on the 12th (Wed) to allow time to drive to Williamsburg.
Parks · Museums · Outdoors · Beaches
Side Trips

Williamsburg — 5 nights

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.
Get out of town with these interesting Williamsburg side-trips: St. Luke's Historic Church & Museum (in Smithfield) and The Mariners' Museum & Park (in Newport News). Spend the 16th (Sun) exploring nature at Colonial National Historical Park. There's lots more to do: get engrossed in the history at Colonial Williamsburg, explore and take pictures at Historic Jamestowne, steep yourself in history at Bassett Hall, and step aboard Jamestown Settlement.

For photos, other places to visit, maps, and tourist information, go to the Williamsburg road trip site.

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. In October in Williamsburg, expect temperatures between 75°F during the day and 55°F at night. Cap off your sightseeing on the 17th (Mon) early enough to go by car to Charlottesville.
Historic Sites · Museums · Parks · Nature
Side Trips

Charlottesville — 5 nights

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 Old Rag Mountain Hike (in Shenandoah National Park), Natural Bridge (Virginia Safari Park & Natural Bridge State Park) and Appomattox Court House National Historical Park (in Appomattox). And it doesn't end there: take in nature's colorful creations at Monticello, experience rural life at Open Gate Farm, indulge your senses at Central Virginia Wine Tours & Transportation, and steep yourself in history at Mulberry Row.

To find other places to visit, ratings, photos, and tourist information, read Charlottesville trip itinerary tool.

Traveling by car from Williamsburg to Charlottesville takes 2.5 hours. Alternatively, you can take a bus; or do a combination of train and bus. Traveling from Williamsburg in October, Charlottesville is slightly colder at night with lows of 49°F. Finish your sightseeing early on the 22nd (Sat) to allow enough time to travel to Bedford.
Historic Sites · Parks · Nature · Tours
Side Trips

Bedford — 3 nights

Bedford is an incorporated town and former independent city located within Bedford County in the U.S. state of Virginia. Explore the numerous day-trip ideas around Bedford: Booker T. Washington National Monument (in Hardy), Smith Mountain Lake (in Moneta) and Patrick Henry's Red Hill (in Brookneal). There's still lots to do: appreciate the history behind National D-Day Memorial, admire the striking features of Thomas Jefferson's Poplar Forest, and experience rural life at A.J. Gross & Sons Orchard.

To find other places to visit, traveler tips, ratings, and more tourist information, use the Bedford driving holiday planning tool.

Drive from Charlottesville to Bedford in 2 hours. October in Bedford sees daily highs of 70°F and lows of 47°F at night. Finish your sightseeing early on the 25th (Tue) to allow enough time to travel to Abingdon.
Historic Sites · Nature · Parks · Museums
Side Trips

Abingdon — 5 nights

Abingdon is a town in Washington County, Virginia, United States, southwest of Roanoke. Go for a jaunt from Abingdon to Mouth of Wilson to see Grayson Highlands State Park about 48 minutes away. There's lots more to do: trek along Virginia Creeper National Recreation Trail, grab your bike and head to Shuttle Shack, see the interesting displays at Star Museum, and gear up at Adventure Damascus.

To find photos, reviews, and other tourist information, go to the Abingdon trip itinerary maker.

Drive from Bedford to Abingdon in 3 hours. In October, daytime highs in Abingdon are 69°F, while nighttime lows are 49°F. Wrap up your sightseeing on the 30th (Sun) early enough to travel back home.
Parks · Trails · Outdoors · Museums
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.