18 days in Virginia Itinerary

18 days in Virginia Itinerary

Created using Inspirock Virginia holiday planner

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Route & dates

18 days in Virginia Itinerary

Start: Detroit
Fly:  4​h 45​min
1
Virginia Beach
— 2 nights
Drive:  2​h 30​min
2
Chincoteague Island
— 4 nights
Drive:  3​h
3
Yorktown
— 3 nights
Drive:  30​min
4
Williamsburg
— 4 nights
Drive:  3​h
5
Appomattox
— 2 nights
Drive:  1​h 30​min
6
Staunton
— 2 nights
bus + Fly:  7​h
End: Detroit

2
nights
Virginia Beach

Virginia Beach ©
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.
Deepen your sense of the past at sights like Cape Henry Lighthouse and Virginia Beach Law Enforcement Memorial. Eschew the tourist crowds and head to Sandbridge Beach and Chrysler Museum of Art. Step out of Virginia Beach to go to Cape Charles and see Chesapeake Bay Bridge-Tunnel, which is approximately 38 minutes away. And it doesn't end there: learn about all things military at Military Aviation Museum, examine the collection at Virginia Beach Surf & Rescue Museum, look for gifts at Mermaid Factory, and admire the majestic nature at First Landing State Park.

To see photos, ratings, more things to do, and more tourist information, read Virginia Beach trip planner.

Detroit to Virginia Beach is an approximately 5-hour flight. You can also do a combination of bus and flight; or drive. Traveling from Detroit in October, things will get somewhat warmer in Virginia Beach: highs are around 74°F and lows about 56°F. Finish your sightseeing early on the 3rd (Thu) so you can drive to Chincoteague Island.

Things to do in Virginia Beach

Parks Museums Outdoors

Side Trips

Chrysler Museum of Art, Chesapeake Bay Bridge-Tunnel
Highlights from your plan
Military Aviation Museum ©
Military Aviation Museum
Sandbridge Beach ©
Sandbridge Beach
First Landing State Park ©
First Landing State Park

4
nights
Chincoteague Island

Famous for a wild breed of horses--Chincoteague Ponies--Chincoteague Island embraces the mystery of some of North America’s oldest inhabitants.
Escape the urban bustle at Nature & Wildlife Tours and Fishing Charters & Tours. Shop till you drop at Tryfan Gallery and MamerSass. Spend the 6th (Sun) exploring nature at Chincoteague National Wildlife Refuge. There's much more to do: get engrossed in the history at Museum of Chincoteague, head outdoors with Donald J. Leonard, and tour the pleasant surroundings at Bike Depot.

To see photos, reviews, other places to visit, and more tourist information, read our Chincoteague Island online travel planner .

Getting from Virginia Beach to Chincoteague Island by car takes about 2.5 hours. Other options: take a bus; or take a bus. In October, daily temperatures in Chincoteague Island can reach 71°F, while at night they dip to 54°F. Finish your sightseeing early on the 7th (Mon) to allow enough time to drive to Yorktown.

Things to do in Chincoteague Island

Wildlife Outdoors Parks
Highlights from your plan
Nature & Wildlife Tours
Chincoteague National Wildlife Refuge ©
Museum of Chincoteague ©
Museum of Chincoteague

3
nights
Yorktown

Yorktown ©
Yorktown is a census-designated place (CDP) in York County, Virginia, United States. American Revolution Museum at Yorktown and York County Historical Museum will appeal to museum buffs. You'll discover tucked-away gems like Colonial Parkway and Yorktown Beach. Venture out of the city with trips to Deltaville Maritime Museum (in Deltaville), Historic Christ Church (in Irvington) and Good Luck Cellars (in Kilmarnock). The adventure continues: look for all kinds of wild species at Savage Neck Dunes Dunes Natural Area Preserve and stop by Whitley's Peanut Factory.

To find ratings, other places to visit, traveler tips, and more tourist information, refer to the Yorktown trip itinerary builder app .

Traveling by car from Chincoteague Island to Yorktown takes 3 hours. Alternatively, you can take a bus; or take a bus. In October, daily temperatures in Yorktown can reach 73°F, while at night they dip to 54°F. Wrap up your sightseeing on the 10th (Thu) early enough to drive to Williamsburg.

Things to do in Yorktown

Outdoors Parks Museums

Side Trips

Deltaville Maritime Museum, Good Luck Cellars, Savage Neck Dunes Dunes Natural Area Preserve, Historic Christ Church, Whitley's Peanut Factory
Highlights from your plan
Yorktown Beach ©
Yorktown Beach
Colonial Parkway ©
Colonial Parkway

4
nights
Williamsburg

Williamsburg ©
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 Carytown and Yankee Candle Companyfor plenty of shopping. Popular historic sites such as Hollywood Cemetery and Bassett Hall are in your itinerary. Explore the numerous day-trip ideas around Williamsburg: The Mariners' Museum & Park (in Newport News), Richmond (Virginia Capitol Building & White House of the Confederacy) and Berkeley Plantation (in Charles City). There's still lots to do: take in the architecture and atmosphere at Bruton Parish Episcopal Church, browse the different shops at Merchants Square, admire the masterpieces at DeWitt Wallace Decorative Arts Museum, and contemplate the long history of Public Hospital Museum.

Plan my trip to Williamsburg with suggested itineraries provided by Inspirock.

Williamsburg is just a short distance from Yorktown. In October in Williamsburg, expect temperatures between 75°F during the day and 55°F at night. Finish up your sightseeing early on the 14th (Mon) so you can travel to Appomattox.

Things to do in Williamsburg

Historic Sites Museums Shopping

Side Trips

Richmond, Berkeley Plantation, The Mariners' Museum & Park
Highlights from your plan
Hollywood Cemetery ©
Hollywood Cemetery
Berkeley Plantation ©
Berkeley Plantation
Bassett Hall ©
Bassett Hall

2
nights
Appomattox

Appomattox ©
Appomattox is a town in Appomattox County, Virginia, United States. On the 15th (Tue), learn about all things military at The American Civil War Museum - Appomattox, contemplate the long history of McLean House, then explore the striking landscape of Appomattox Court House National Historical Park, and finally take in the history at Appomattox Station Battlefield Park. Get ready for a full day of sightseeing on the next day: browse the exhibits of Patrick Henry's Red Hill and then immerse yourself in nature at High Bridge Trail State Park.

To see more things to do, traveler tips, and other tourist information, you can read our Appomattox trip builder website .

You can drive from Williamsburg to Appomattox in 2.5 hours. Prepare for a bit cooler weather when traveling from Williamsburg in October: high temperatures in Appomattox hover around 70°F and lows are around 47°F. Wrap up your sightseeing on the 16th (Wed) to allow time to travel to Staunton.

Things to do in Appomattox

Historic Sites Nature Parks

Side Trips

Patrick Henry's Red Hill, High Bridge Trail State Park
Highlights from your plan
McLean House ©
McLean House

2
nights
Staunton

Staunton ©
Staunton is an independent city in the U.S. On the 17th (Thu), contemplate the long history of Frontier Culture Museum and then savor the flavors at King Family Vineyards. Keep things going the next day: examine the collection at Camera Heritage Museum, then examine the collection at Woodrow Wilson Presidential Library and Museum, and then steep yourself in history at Lee Chapel and Museum.

To find other places to visit, ratings, maps, and tourist information, use the Staunton driving holiday planner .

Drive from Appomattox to Staunton in 2 hours. In October, daily temperatures in Staunton can reach 68°F, while at night they dip to 45°F. Finish your sightseeing early on the 18th (Fri) to allow enough time to travel back home.

Things to do in Staunton

Museums Shopping Wineries

Side Trips

Lee Chapel and Museum, King Family Vineyards
Highlights from your plan
Frontier Culture Museum ©
Frontier Culture Museum
Lee Chapel and Museum ©
Lee Chapel and Museum
King Family Vineyards ©
King Family Vineyards

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