11 days in Virginia Itinerary
Created using Inspirock Virginia journey planner
Start: Anchorage
Fly
1
Charlottesville
— 1 night
Drive
2
Floyd
— 1 night
Drive
3
Winchester
— 1 night
Drive
4
Arlington
— 1 night
Fly
5
Williamsburg
— 3 nights
Drive
6
Virginia Beach
— 3 nights
Fly
End: Anchorage
Wed, Oct 5 - Sat, Oct 15
Edit
| S | M | T | W | T | F | S |
|---|---|---|---|---|---|---|
|
2
|
3
|
4
|
5
|
6
|
7
|
8
|
|
9
|
10
|
11
|
12
|
13
|
14
|
15
|
View full calendar
Charlottesville — 1 night
©
Hoo-Ville
Kick off your visit on the 6th (Thu): do a tasting at King Family Vineyards and then take in nature's colorful creations at Monticello.
To find where to stay, other places to visit, and tourist information, refer to the Charlottesville road trip planning website.
Anchorage to Charlottesville is an approximately 11-hour flight. You can also drive. The time zone changes from Alaska Standard Time (AKST) to Eastern Standard Time (EST), which is usually a 4 hour difference. When traveling from Anchorage in October, plan for warmer days in Charlottesville, with highs around 71°F, while nights are somewhat warmer with lows around 49°F. Finish your sightseeing early on the 6th (Thu) so you can drive to Floyd.
more
To find where to stay, other places to visit, and tourist information, refer to the Charlottesville road trip planning website.
Anchorage to Charlottesville is an approximately 11-hour flight. You can also drive. The time zone changes from Alaska Standard Time (AKST) to Eastern Standard Time (EST), which is usually a 4 hour difference. When traveling from Anchorage in October, plan for warmer days in Charlottesville, with highs around 71°F, while nights are somewhat warmer with lows around 49°F. Finish your sightseeing early on the 6th (Thu) so you can drive to Floyd.
Side Trip
Find places to stay Oct 5 — 6:
Highlights from your trip
Floyd — 1 night
©
Kick off your visit on the 7th (Fri): take in the exciting artwork at Bell Gallery and Garden, browse for treasures at Finders Keepers, then take in the exciting artwork at Troika Contemporary Crafts, and finally stop by Floyd Country Store.
To see other places to visit, traveler tips, photos, and other tourist information, you can read our Floyd trip planner.
Use the Route module to find suitable travel options from Charlottesville to Floyd. Plan for little chillier nights when traveling from Charlottesville in October since evenings lows in Floyd dip to 44°F. Cap off your sightseeing on the 7th (Fri) early enough to go by car to Winchester.
more
To see other places to visit, traveler tips, photos, and other tourist information, you can read our Floyd trip planner.
Use the Route module to find suitable travel options from Charlottesville to Floyd. Plan for little chillier nights when traveling from Charlottesville in October since evenings lows in Floyd dip to 44°F. Cap off your sightseeing on the 7th (Fri) early enough to go by car to Winchester.
Find places to stay Oct 6 — 7:
Highlights from your trip
Winchester — 1 night
©
Start off your visit on the 8th (Sat): relax in the rural setting at Marker-Miller Orchards, pick up a one of a kind souvenir at Strasburg Emporium Antiques, and then take in the exciting artwork at Shenandoah Valley Artworks.
To find traveler tips, ratings, and tourist information, you can read our Winchester attractions app.
Explore your travel options from Floyd to Winchester with the Route module. In October, daily temperatures in Winchester can reach 67°F, while at night they dip to 46°F. Wrap up your sightseeing on the 8th (Sat) to allow time to drive to Arlington.
more
To find traveler tips, ratings, and tourist information, you can read our Winchester attractions app.
Explore your travel options from Floyd to Winchester with the Route module. In October, daily temperatures in Winchester can reach 67°F, while at night they dip to 46°F. Wrap up your sightseeing on the 8th (Sat) to allow time to drive to Arlington.
Side Trip
Find places to stay Oct 7 — 8:
Highlights from your trip
Arlington — 1 night
©
National History, Local Flavor
On the 9th (Sun), get to know the fascinating history of The Tomb of the Unknown Soldier, stroll the grounds of Arlington National Cemetery, then look for gifts at The Spice & Tea Exchange® of Alexandria, and finally take in the exciting artwork at Torpedo Factory Art Center.
To find more things to do, traveler tips, other places to visit, and more tourist information, use the Arlington trip itinerary maker tool.
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 bus. Traveling from Winchester in October, plan for somewhat warmer nights in Arlington, with lows around 54°F. Finish your sightseeing early on the 9th (Sun) to allow enough time to fly to Williamsburg.
more
To find more things to do, traveler tips, other places to visit, and more tourist information, use the Arlington trip itinerary maker tool.
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 bus. Traveling from Winchester in October, plan for somewhat warmer nights in Arlington, with lows around 54°F. Finish your sightseeing early on the 9th (Sun) to allow enough time to fly to Williamsburg.
Side Trip
Find places to stay Oct 8 — 9:
Highlights from your trip
Williamsburg — 3 nights
©
Colonial Capital
Popular historic sites such as Colonial Williamsburg and Jamestown Settlement are in your itinerary. Give yourself a bit of retail therapy at Yankee Candle Village and Williamsburg Art Gallery. There's still lots to do: contemplate the long history of Historic Jamestowne, buy something for everyone on your list at Merchants Square, and find something for the whole family at Busch Gardens Williamsburg.
To see other places to visit, reviews, maps, and other tourist information, read Williamsburg road trip app.
Fly from Arlington to Williamsburg in 3 hours. Alternatively, you can drive; or do a combination of subway and train. In October, plan for daily highs up to 75°F, and evening lows to 55°F. Finish up your sightseeing early on the 12th (Wed) so you can go by car to Virginia Beach.
more
To see other places to visit, reviews, maps, and other tourist information, read Williamsburg road trip app.
Fly from Arlington to Williamsburg in 3 hours. Alternatively, you can drive; or do a combination of subway and train. In October, plan for daily highs up to 75°F, and evening lows to 55°F. Finish up your sightseeing early on the 12th (Wed) so you can go by car to Virginia Beach.
Find places to stay Oct 9 — 12:
Highlights from your trip
Virginia Beach — 3 nights
©
The Resort City
You'll get in some beach time at Virginia Beach and Croatan Beach. Do your shopping at Brock Environmental Center - Chesapeake Bay Foundation and Lynnhaven Mall. Explore Virginia Beach's surroundings by going to Cape Charles Beach (in Cape Charles), Barrier Islands Center (in Machipongo) and Skipjack Nautical Wares & Marine Art Gallery (in Portsmouth). The adventure continues: take a leisurely stroll along Virginia Beach Boardwalk.
To find traveler tips, maps, photos, and other tourist information, refer to the Virginia Beach road trip tool.
Getting from Williamsburg to Virginia Beach by car takes about 1.5 hours. Other options: take a bus; or do a combination of train and bus. In October, daily temperatures in Virginia Beach can reach 74°F, while at night they dip to 56°F. Cap off your sightseeing on the 15th (Sat) early enough to catch the flight back home.
more
To find traveler tips, maps, photos, and other tourist information, refer to the Virginia Beach road trip tool.
Getting from Williamsburg to Virginia Beach by car takes about 1.5 hours. Other options: take a bus; or do a combination of train and bus. In October, daily temperatures in Virginia Beach can reach 74°F, while at night they dip to 56°F. Cap off your sightseeing on the 15th (Sat) early enough to catch the flight back home.
Side Trips
Find places to stay Oct 12 — 15:
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.
