24 days in Virginia Itinerary
Created using Inspirock Virginia trip planner
Start: Kuwait City
Fly to Washington Dulles International Airport, Drive to Winchester
1
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
End: Kuwait City
Tue, Oct 25 - Thu, Nov 17
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Winchester — 2 nights
©
Winchester is an independent city located in the northwestern portion of the Commonwealth of Virginia. Here are some ideas for day two: pick up some local products at Virginia Farm Market, shop like a local with Gallery On Madison, and then do a tasting at Mediterranean Cellars.
To find other places to visit, where to stay, ratings, and tourist information, you can read our Winchester trip site.
Kuwait City, Kuwait to Winchester is an approximately 19-hour combination of flight and car. You'll gain 8 hours traveling from Kuwait City to Winchester due to the time zone difference. Traveling from Kuwait City in October, things will get much colder in Winchester: highs are around 67°F and lows about 46°F. Finish your sightseeing early on the 27th (Thu) so you can drive to Floyd.
more
To find other places to visit, where to stay, ratings, and tourist information, you can read our Winchester trip site.
Kuwait City, Kuwait to Winchester is an approximately 19-hour combination of flight and car. You'll gain 8 hours traveling from Kuwait City to Winchester due to the time zone difference. Traveling from Kuwait City in October, things will get much colder in Winchester: highs are around 67°F and lows about 46°F. Finish your sightseeing early on the 27th (Thu) so you can drive to Floyd.
Side Trips
Find places to stay Oct 25 — 27:
Highlights from your trip
Floyd — 3 nights
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Floyd is a town in Floyd County, Virginia, United States. Shop till you drop at Floyd Country Store and Floyd Farmers Market. Explore Floyd's surroundings by going to Southwest Virginia Farmers Market (in Hillsville) and Foggy Ridge Cider (in Dugspur). There's lots more to do: pick up a one of a kind souvenir at Finders Keepers, learn about winemaking at Chateau Morrisette Winery, sample the fine beverages at Five Mile Mountain Distillery, and steep yourself in history at Cockram Mill.
Plan a trip to Floyd easily and quickly by telling Inspirock to suggest an itinerary.
You can drive from Winchester to Floyd in 3.5 hours. In October in Floyd, expect temperatures between 67°F during the day and 44°F at night. Finish your sightseeing early on the 30th (Sun) so you can drive to Orange.
more
Plan a trip to Floyd easily and quickly by telling Inspirock to suggest an itinerary.
You can drive from Winchester to Floyd in 3.5 hours. In October in Floyd, expect temperatures between 67°F during the day and 44°F at night. Finish your sightseeing early on the 30th (Sun) so you can drive to Orange.
Side Trips
Find places to stay Oct 27 — 30:
Highlights from your trip
Orange — 1 night
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Orange is a town in, and county seat of, Orange County, Virginia, United States. Kick off your visit on the 31st (Mon): take in the exciting artwork at The Arts Center in Orange, brush up on your knowledge of spirits at Belmont Farms Distillery, then pick up a one of a kind souvenir at Finders Keepers, and finally awaken your taste buds at Central Virginia Wine Tours & Transportation.
For maps, ratings, other places to visit, and other tourist information, you can read our Orange sightseeing planner.
You can drive from Floyd to Orange in 3.5 hours. Another option is to drive. October in Orange sees daily highs of 70°F and lows of 48°F at night. Finish your sightseeing early on the 31st (Mon) so you can drive to Richmond.
more
For maps, ratings, other places to visit, and other tourist information, you can read our Orange sightseeing planner.
You can drive from Floyd to Orange in 3.5 hours. Another option is to drive. October in Orange sees daily highs of 70°F and lows of 48°F at night. Finish your sightseeing early on the 31st (Mon) so you can drive to Richmond.
Side Trip
Find places to stay Oct 30 — 31:
Highlights from your trip
Richmond — 4 nights
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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.Head to King Family Vineyards and Tom Leonard's Farmer's Marketfor plenty of shopping. You'll find plenty of places to visit near Richmond: Charlottesville (Kluge-Ruhe Aboriginal Art Collection of the University of Virginia & Monticello), Washington DC (White House, Washington Monument, &more) and iLoveKickboxing.com (in Glen Allen). The adventure continues: take a stroll through Carytown, get a taste of the local shopping with Short Pump Mall, learn about winemaking at Blue Bee Cider, and brush up on your military savvy at White House of the Confederacy.
To find traveler tips, photos, other places to visit, and more tourist information, go to the Richmond trip planner.
Drive from Orange to Richmond in 1.5 hours. Expect a daytime high around 73°F in October, and nighttime lows around 51°F. Cap off your sightseeing on the 4th (Fri) early enough to go by car to Williamsburg.
Side Trips
Find places to stay Oct 31 — Nov 4:
Highlights from your trip
Williamsburg — 5 nights
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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.Shop till you drop at Plantation Peanuts of Wakefield and Yorktown Market Days. Plan for a day of cool, family-friendly fun on the 6th (Sun) at Busch Gardens Williamsburg. Next up on the itinerary: make a trip to Colonial Williamsburg, revel in the low prices at Williamsburg Premium Outlets, browse the different shops at Williamsburg Antique Mall, and tour the pleasant surroundings at Yorktown Beach.
To find where to stay, reviews, maps, and tourist information, read our Williamsburg itinerary app.
You can drive from Richmond to Williamsburg in an hour. Alternatively, you can take a train; or take a bus. In November in Williamsburg, expect temperatures between 63°F during the day and 42°F at night. Finish your sightseeing early on the 9th (Wed) to allow enough time to drive to Virginia Beach.
Side Trips
Find places to stay Nov 4 — 9:
Highlights from your trip
Virginia Beach — 4 nights
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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.Shop till you drop at Gull Hummock Gourmet Market and Brock Environmental Center - Chesapeake Bay Foundation. You'll get in some beach time at Virginia Beach and Grommet Island Park. Change things up with these side-trips from Virginia Beach: Cape Charles (Stage Door Gallery & Cape Charles Beach), Scotch and Soda the Lions (in Norfolk) and Chatham Vineyards (in Machipongo). Next up on the itinerary: brush up on your knowledge of spirits at Tarnished Truth Distilling Co., indulge your thirst for a good beer at New Realm Brewing, make a trip to Flame of Hope Memorial, and brush up on your military savvy at Military Aviation Museum.
For ratings, where to stay, and more tourist information, read Virginia Beach trip itinerary maker app.
Traveling by car from Williamsburg to Virginia Beach takes 1.5 hours. Alternatively, you can take a bus; or do a combination of train and bus. In November, daily temperatures in Virginia Beach can reach 62°F, while at night they dip to 43°F. Finish your sightseeing early on the 13th (Sun) so you can fly to Alexandria.
Side Trips
Find places to stay Nov 9 — 13:
Highlights from your trip
Alexandria — 3 nights
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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 Village at Shirlington. Change things up with these side-trips from Alexandria: Divine Wine Tours of Virginia (in Reston) and Dale City Farmers' Market (in Dale City). Next up on the itinerary: wander the streets of Old Town, view the masterpieces at Torpedo Factory Art Center, get to know the fascinating history of The Tomb of the Unknown Soldier, and stroll the grounds of Arlington National Cemetery.
To see reviews, photos, where to stay, and other tourist information, you can read our Alexandria attractions planner.
You can fly from Virginia Beach to Alexandria in 3 hours. Other options are to drive; or take a train. In November in Alexandria, expect temperatures between 59°F during the day and 42°F at night. Finish your sightseeing early on the 16th (Wed) to allow enough time to travel back home.
Side Trips
Arlington, Divine Wine Tours of Virginia, Dale City Farmers' Market, Tysons Galleria Shopping Center, Buckland Farm Market
Find places to stay Nov 13 — 16:
Highlights from your trip
Virginia travel guide
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.
