14 days in Virginia Itinerary

14 days in Virginia Itinerary

Created using Inspirock Virginia visit planner

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Route & dates

14 days in Virginia Itinerary

Start: Detroit
Fly:  4​h
1
Arlington
— 3 nights
Drive:  1​h 30​min
2
Winchester
— 3 nights
Drive:  4​h
3
Smithfield
— 3 nights
Drive:  1​h 30​min
4
Richmond
— 4 nights
Fly:  5​h
End: Detroit

3
nights
Arlington

Arlington ©
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: Inside Ski Training Center (in Leesburg), Steven F. Udvar-Hazy Center (in Chantilly) and National Museum of the Marine Corps (in Triangle). Next up on the itinerary: explore the different monuments and memorials at Arlington National Cemetery, pause for some serene contemplation at Our Lady Queen of Peace Catholic Church, get your game on at iFLY Indoor Skydiving - Loudoun, and step off the mainland to explore Theodore Roosevelt Island Park.

To find more things to do, reviews, photos, and other tourist information, use the Arlington travel route builder tool .

Detroit to Arlington is an approximately 4-hour flight. You can also do a combination of flight, bus, and subway; or drive. Traveling from Detroit in December, expect Arlington to be a bit warmer, temps between 51°F and 37°F. Finish up your sightseeing early on the 26th (Thu) so you can go by car to Winchester.

Things to do in Arlington

Parks Historic Sites Outdoors

Side Trips

iFLY Indoor Skydiving - Loudoun, Steven F. Udvar-Hazy Center, Room Escape Games, Inside Ski Training Center, National Museum of the Marine Corps
Find places to stay Dec 23 — 26:
Highlights from your plan
Arlington National Cemetery ©
Arlington National Cemetery
The Tomb of the Unknown Soldier ©
The Tomb of the Unknown Soldier
Mount Vernon Trail ©
Mount Vernon Trail

3
nights
Winchester

Winchester ©
Winchester is an independent city located in the northwestern portion of the Commonwealth of Virginia. Explore the numerous day-trip ideas around Winchester: Sperryville (Copper Fox Distillery & Cooter's in the Country), Shenandoah National Park (Old Rag Mountain Hike & Appalachian Trail) and Luray (River Hill Wine & Spirits & Stony Man Mountain Hike). Next up on the itinerary: wander the wide-open spaces of Rocking S Ranch, shop like a local with Marker-Miller Orchards, sample the tasty concoctions at Escutcheon Brewing Co, and see the interesting displays at Virginia Museum of Veiled History.

To see where to stay, photos, traveler tips, and other tourist information, refer to the Winchester trip itinerary planning site .

Drive from Arlington to Winchester in 1.5 hours. Alternatively, you can take a bus; or take a train. Plan for little chillier nights when traveling from Arlington in December since evenings lows in Winchester dip to 31°F. Wrap up your sightseeing on the 29th (Sun) early enough to travel to Smithfield.

Things to do in Winchester

Parks Outdoors Trails

Side Trips

Sperryville, Luray, Shenandoah National Park, Cascade Falls
Find places to stay Dec 26 — 29:
Highlights from your plan
Rocking S Ranch ©
Rocking S Ranch
Old Rag Mountain Hike ©
Old Rag Mountain Hike
Escutcheon Brewing Co ©
Escutcheon Brewing Co

3
nights
Smithfield

Smithfield ©
Smithfield is a town in Isle of Wight County, in the South Hampton Roads subregion of the Hampton Roads region of Virginia in the United States. Explore Smithfield's surroundings by going to Williamsburg (Colonial Williamsburg Musket Range, Colonial Williamsburg, & more), Chrysler Museum of Art (in Norfolk) and Moore House (in Yorktown). There's still lots to do: contemplate the long history of St. Luke's Historic Church & Museum, look for gifts at The Christmas Store, trek along The Noland Trail, and browse the exhibits of The Mariners' Museum & Park.

To find other places to visit, photos, traveler tips, and tourist information, read Smithfield holiday planning tool .

You can drive from Winchester to Smithfield in 4 hours. Traveling from Winchester in December, expect Smithfield to be a bit warmer, temps between 54°F and 38°F. Finish up your sightseeing early on the 1st (Wed) so you can go by car to Richmond.

Things to do in Smithfield

Museums Historic Sites Parks

Side Trips

Williamsburg, Newport News, Moore House, Chrysler Museum of Art
Find places to stay Dec 29 — Jan 1:
Highlights from your plan
Colonial Williamsburg ©
Colonial Williamsburg
St. Luke's Historic Church & Museum ©
Windsor Castle Park ©
Windsor Castle Park

4
nights
Richmond

Richmond ©
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.
You'll find plenty of places to visit near Richmond: Charlottesville (Monticello & Jefferson School African American Heritage Center), Orange (Finders Keepers, St. Thomas Parish Church, & more) and Escape Old Towne - Escape Rooms (in Petersburg). Next up on the itinerary: admire the masterpieces at Virginia Museum of Fine Arts, shop like a local with Shockoe Bottom Clay, explore the different monuments and memorials at Blandford Church and Cemetery, and appreciate the history behind Bill Bojangles Robinson Monument.

To see photos, ratings, other places to visit, and other tourist information, use the Richmond tour planner .

Traveling by car from Smithfield to Richmond takes 1.5 hours. In January, plan for daily highs up to 47°F, and evening lows to 28°F. Finish your sightseeing early on the 5th (Sun) to allow enough time to travel back home.

Things to do in Richmond

Historic Sites Museums Fun & Games

Side Trips

Orange, Charlottesville, Petersburg, Cold Harbor National Cemetery
Find places to stay Jan 1 — 5:
Highlights from your plan
Blandford Church and Cemetery ©
Blandford Church and Cemetery
Virginia Museum of Fine Arts ©
Virginia Museum of Fine Arts
Monticello ©
Monticello

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