24 days in Virginia Itinerary

24 days in Virginia Itinerary

Created using Inspirock Virginia trip planner
Make it your trip
Fly to Washington Dulles International Airport, Drive to Winchester
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Winchester
— 2 nights
Drive
2
Floyd
— 3 nights
Drive
3
Orange
— 1 night
Drive
4
Richmond
— 4 nights
Drive
5
Williamsburg
— 5 nights
Drive
6
Virginia Beach
— 4 nights
Fly
7
Alexandria
— 3 nights
Drive to Ronald Reagan Washington National Airport, Fly to Kuwait City

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Winchester — 2 nights

Winchester is an independent city located in the northwestern portion of the Commonwealth of Virginia. Get ready for a full day of sightseeing on the 9th (Sun): browse the fresh offerings at Virginia Farm Market, then get a taste of the local shopping with Gallery On Madison, and then do a tasting at Mediterranean Cellars.

To see where to stay, ratings, more things to do, and more tourist information, you can read our Winchester travel planning website.

Kuwait City, Kuwait to Winchester is an approximately 19-hour combination of flight and car. The time zone difference when traveling from Kuwait City to Winchester is minus 8 hours. Prepare for cooler weather when traveling from Kuwait City in October: high temperatures in Winchester hover around 22°C and lows are around 9°C. Finish up your sightseeing early on the 10th (Mon) so you can go by car to Floyd.
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Shopping · Wineries · Museums
Side Trips
Find places to stay Oct 8 — 10:

Floyd — 3 nights

Floyd is a town in Floyd County, Virginia, United States. Shop till you drop at Floyd Country Store and Bell Gallery and Garden. Explore Floyd's surroundings by going to Southwest Virginia Farmers Market (in Hillsville) and Foggy Ridge Cider (in Dugspur). And it doesn't end there: pick up a one of a kind souvenir at Finders Keepers, sample the fine beverages at Five Mile Mountain Distillery, learn about winemaking at Villa Appalaccia Winery, and find something for the whole family at Buffalo Mountain Ziplines.

To see where to stay, photos, traveler tips, and tourist information, you can read our Floyd trip itinerary planning website.

Getting from Winchester to Floyd by car takes about 3.5 hours. In October, daily temperatures in Floyd can reach 22°C, while at night they dip to 7°C. Wrap up your sightseeing on the 13th (Thu) to allow time to drive to Orange.
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Find places to stay Oct 10 — 13:

Orange — 1 night

Orange is a town in, and county seat of, Orange County, Virginia, United States. Start off your visit on the 14th (Fri): view the masterpieces at The Arts Center in Orange, brush up on your knowledge of spirits at Belmont Farms Distillery, then look for gifts at Finders Keepers, and finally do sightseeing your way with Central Virginia Wine Tours & Transportation.

To find more things to do, traveler tips, where to stay, and more tourist information, go to the Orange day trip planner.

Drive from Floyd to Orange in 3.5 hours. Alternatively, you can drive. In October in Orange, expect temperatures between 24°C during the day and 10°C at night. Finish up your sightseeing early on the 14th (Fri) so you can go by car to Richmond.
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Shopping · Wineries · Breweries & Distilleries · Tours
Side Trip
Find places to stay Oct 13 — 14:

Richmond — 4 nights

The River City

The capital city of Virginia, Richmond has diverse architecture, a large collection of monuments, and world-class museums that reveal the city's important role in American history.
Shop till you drop at King Family Vineyards and Short Pump Mall. Venture out of the city with trips to iLoveKickboxing.com (in Glen Allen), Washington DC (White House, Washington Monument, &more) and Charlottesville (Kluge-Ruhe Aboriginal Art Collection of the University of Virginia & Monticello). The adventure continues: take a stroll through Carytown, get a taste of the local shopping with Tom Leonard's Farmer's Market, do a tasting at Blue Bee Cider, and learn about all things military at White House of the Confederacy.

For maps, photos, reviews, and more tourist information, use the Richmond trip itinerary maker app.

Drive from Orange to Richmond in 1.5 hours. In October, daytime highs in Richmond are 26°C, while nighttime lows are 12°C. Finish up your sightseeing early on the 18th (Tue) so you can go by car to Williamsburg.
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Find places to stay Oct 14 — 18:

Williamsburg — 5 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.
Head to Plantation Peanuts of Wakefield and Williamsburg Art Galleryfor some retail therapy. Plan for a day of cool, family-friendly fun on the 20th (Thu) at Busch Gardens Williamsburg. And it doesn't end there: contemplate the long history of Colonial Williamsburg, browse the exhibits of Historic Jamestowne, make a trip to St. George Tucker House, and step aboard Jamestown Settlement.

To find more things to do, where to stay, photos, and more tourist information, go to the Williamsburg road trip planning site.

You can drive from Richmond to Williamsburg in an hour. Alternatively, you can take a train; or take a bus. In October in Williamsburg, expect temperatures between 28°C during the day and 15°C at night. Cap off your sightseeing on the 23rd (Sun) early enough to go by car to Virginia Beach.
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Find places to stay Oct 18 — 23:

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.
For shopping fun, head to Gull Hummock Gourmet Market or Brock Environmental Center - Chesapeake Bay Foundation. Visit Virginia Beach and Grommet Island Park for some beach relaxation. You'll find plenty of places to visit near Virginia Beach: Scotch and Soda the Lions (in Norfolk), Chatham Vineyards (in Machipongo) and Cape Charles (Stage Door Gallery & Cape Charles Beach). There's much more to do: brush up on your knowledge of spirits at Tarnished Truth Distilling Co., browse the different shops at Lynnhaven Mall, indulge your thirst for a good beer at New Realm Brewing, and don't miss a visit to Flame of Hope Memorial.

To see ratings, reviews, other places to visit, and other tourist information, use the Virginia Beach driving holiday website.

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 October, daytime highs in Virginia Beach are 27°C, while nighttime lows are 15°C. Wrap up your sightseeing on the 27th (Thu) early enough to fly to Alexandria.
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Shopping · Beaches · Outdoors · Parks
Side Trips
Find places to stay Oct 23 — 27:

Alexandria — 3 nights

Just a few metro stops away from the bustle of Washington D.C., Alexandria provides a respite from the fast-paced capital.
Do your shopping at Buckland Farm Market and Tysons Galleria Shopping Center. Get out of town with these interesting Alexandria side-trips: Dale City Farmers' Market (in Dale City) and Divine Wine Tours of Virginia (in Reston). There's much more to do: wander the streets of Old Town, buy something for everyone on your list at Village at Shirlington, appreciate the extensive heritage of The Tomb of the Unknown Soldier, and take in the exciting artwork at Torpedo Factory Art Center.

To see other places to visit, maps, reviews, and other tourist information, you can read our Alexandria online sightseeing planner.

Fly from Virginia Beach to Alexandria in 3 hours. Alternatively, you can drive; or take a train. October in Alexandria sees daily highs of 25°C and lows of 14°C at night. Wrap up your sightseeing on the 30th (Sun) early enough to travel back home.
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Shopping · Historic Sites · Wineries · Tours
Side Trips
Find places to stay Oct 27 — 30:

Virginia travel guide

4.5
Historic Sites · Wineries & Vineyards · Gardens
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.
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