31 days in South Dakota & Virginia Itinerary

31 days in South Dakota & Virginia Itinerary

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Route & dates

31 days in South Dakota & Virginia Itinerary

Start: New York City
bus + Fly:  7​h
1
Rapid City
— 4 nights
Fly:  5​h 30​min
2
Alexandria
— 2 nights
Drive:  1​h 30​min
3
Front Royal
— 5 nights
Drive:  1​h 45​min
4
Charlottesville
— 5 nights
Drive:  2​h 15​min
5
Williamsburg
— 5 nights
Drive:  1​h 15​min
6
Virginia Beach
— 5 nights
Drive:  2​h 30​min
7
Chincoteague Island
— 3 nights
Drive:  5​h 15​min
End: New York City

4
nights
Rapid City

Rapid City ©
South Dakota's second-largest city, Rapid City has for many years served as a gateway to the West.
Get some cultural insight at Downtown Rapid City and Firehouse Wine Cellars. Escape the urban bustle at Mount Rushmore National Memorial and Black Hills National Forest. Change things up with a short trip to Custer State Park in Custer (about 42 minutes away). Plan for a day of cool, family-friendly fun on the 4th (Sun) at WaTiki Indoor Waterpark Resort. There's much more to do: identify plant and animal life at Bear Country USA, view the masterpieces at Suzie Cappa Art Center, get engrossed in the history at Pawnseum, and do a tasting at Prairie Berry Winery.

For ratings, reviews, where to stay, and tourist information, read Rapid City route builder .

New York City to Rapid City is an approximately 7-hour combination of bus and flight. You can also drive; or do a combination of train and bus. The time zone difference when traveling from New York City to Rapid City is minus 2 hours. Traveling from New York City in August, you can expect nighttime temperatures to be little chillier in Rapid City, with lows of 60°F. Wrap up your sightseeing on the 5th (Mon) to allow time to travel to Alexandria.

Things to do in Rapid City

Parks Nature Theme Parks

Side Trips

Custer, Prairie Berry Winery, Mount Rushmore National Memorial
Highlights from your plan
Mount Rushmore National Memorial ©
Custer State Park ©
Custer State Park
Black Hills National Forest ©
Black Hills National Forest

2
nights
Alexandria

Alexandria ©
Just a few metro stops away from the bustle of Washington D.C., Alexandria provides a respite from the fast-paced capital.
Get a sense of the local culture at Old Town and Tomb of the Unknowns. Explore Alexandria's surroundings by going to National Museum of the Marine Corps (in Triangle), KO Distilling (in Manassas) and Steven F. Udvar-Hazy Center (in Chantilly). And it doesn't end there: stroll the grounds of Arlington National Cemetery, sample the fine beverages at MurLarkey Distilled Spirits, admire the landmark architecture of George Washington's Mount Vernon, and pause for some serene contemplation at Our Lady Queen of Peace Catholic Church.

To find more things to do, traveler tips, where to stay, and other tourist information, you can read our Alexandria online route maker .

You can fly from Rapid City to Alexandria in 5.5 hours. Other options are to do a combination of flight and train; or drive. The time zone difference moving from Mountain Standard Time to Eastern Standard Time is 2 hours. Plan for somewhat warmer nights when traveling from Rapid City in August since evenings lows in Alexandria dip to 71°F. Wrap up your sightseeing on the 8th (Thu) early enough to drive to Front Royal.

Things to do in Alexandria

Historic Sites Museums Breweries & Distilleries

Side Trips

Arlington, Steven F. Udvar-Hazy Center, KO Distilling, National Museum of the Marine Corps, MurLarkey Distilled Spirits
Highlights from your plan
The Tomb of the Unknown Soldier ©
The Tomb of the Unknown Soldier
Arlington National Cemetery ©
Arlington National Cemetery
National Museum of the Marine Corps ©

5
nights
Front Royal

Front Royal ©
Front Royal is a town in Warren County, Virginia, United States. Get in touch with nature at Luray Caverns and Shenandoah Valley Golf Club. Granite Heights Winery and Rappahannock Cellars are good opportunities to explore the local culture. You'll find plenty of places to visit near Front Royal: Desert Rose Ranch & Winery (in Hume), Fox Meadow Winery (in Linden) and Copper Fox Distillery (in Sperryville). Next up on the itinerary: learn about winemaking at Village Winery, get engrossed in the history at Balthis House, take in the architecture and atmosphere at St. John the Baptist Roman Catholic Church, and brush up on your knowledge of spirits at Catoctin Creek Distillery.

To see maps, other places to visit, where to stay, and more tourist information, go to the Front Royal attractions website .

Getting from Alexandria to Front Royal by car takes about 1.5 hours. In August, Front Royal is a bit cooler than Alexandria - with highs of 82°F and lows of 62°F. Finish up your sightseeing early on the 13th (Tue) so you can go by car to Charlottesville.

Things to do in Front Royal

Wineries Outdoors Golf

Side Trips

Luray, Desert Rose Ranch & Winery, Rappahannock Cellars, Trinity Episcopal Church, Valerie Hill Vineyard & Winery
Highlights from your plan
Granite Heights Winery ©
Granite Heights Winery
Luray Caverns ©
Luray Caverns
Copper Fox Distillery ©
Copper Fox Distillery

5
nights
Charlottesville

Charlottesville ©
Situated at the foothills of the Blue Ridge Mountains, Charlottesville is perhaps best known as the home of three of the United States' founding fathers, including Thomas Jefferson.
Thomas Jefferson's Monticello and Stone Mountain Vineyards are good opportunities to explore the local culture. Get out of town with these interesting Charlottesville side-trips: Barren Ridge Vineyards (in Fishersville), Moss Vineyards (in Dyke) and Nellysford (Hill Top Berry Farm & Winery & Bold Rock Hard Cider). Spend the 16th (Fri) exploring nature at Ivy Creek Natural Area. And it doesn't end there: learn about winemaking at Cooper Vineyards, take in the architecture and atmosphere at Holy Comforter Roman Catholic Church, indulge your taste buds at King Family Vineyards, and sample the tasty concoctions at Starr Hill Brewery.

For ratings, other places to visit, more things to do, and more tourist information, you can read our Charlottesville itinerary planner.

You can drive from Front Royal to Charlottesville in 2 hours. In August, plan for daily highs up to 84°F, and evening lows to 65°F. Finish up your sightseeing early on the 18th (Sun) so you can go by car to Williamsburg.

Things to do in Charlottesville

Wineries Parks Nature

Side Trips

Nellysford, Crozet, Dyke, Barren Ridge Vineyards, Cooper Vineyards
Highlights from your plan
King Family Vineyards ©
King Family Vineyards
Monticello ©
Monticello
Stone Mountain Vineyards ©
Stone Mountain Vineyards

5
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.
Your cultural itinerary includes sights like Colonial Williamsburg and The Hague Winery. Explore the numerous day-trip ideas around Williamsburg: General's Ridge Vineyard and Winery (in Hague), St. Luke's Historic Church & Museum (in Smithfield) and Virginia Museum of Fine Arts (in Richmond). There's lots more to do: tour the pleasant surroundings at Yorktown Beach, steep yourself in history at Historic Jamestowne, take a tour of Jamestown Settlement, and sample the tasty concoctions at Alewerks Brewing Company.

To see traveler tips, more things to do, maps, and other tourist information, you can read our Williamsburg tour builder site .

Drive from Charlottesville to Williamsburg in 2.5 hours. Alternatively, you can take a bus. In August in Williamsburg, expect temperatures between 89°F during the day and 70°F at night. Finish up your sightseeing early on the 23rd (Fri) so you can go by car to Virginia Beach.

Things to do in Williamsburg

Historic Sites Museums Wineries

Side Trips

Hague, Virginia Museum of Fine Arts, St. Luke's Historic Church & Museum, Yorktown Beach
Highlights from your plan
Colonial Williamsburg ©
Colonial Williamsburg
Historic Jamestowne ©
Historic Jamestowne
St. Luke's Historic Church & Museum ©

5
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.
Military Aviation Museum and Virginia Beach Law Enforcement Memorial are good opportunities to explore the local culture. Take a break from the city and head to Virginia Beach and Grommet Island Park. Change things up with a short trip to Cape Charles Beach in Cape Charles (about 1 hour away). There's much more to do: enjoy the sand and surf at Sandbridge Beach, sample the fine beverages at Tarnished Truth Distilling Company, examine the collection at Virginia Beach Surf & Rescue Museum, and see what you can catch with a fishing tour.

For maps, photos, where to stay, and more tourist information, use the Virginia Beach online tour planner .

You can drive from Williamsburg to Virginia Beach in 1.5 hours. Alternatively, you can take a bus; or take a bus. August in Virginia Beach sees daily highs of 86°F and lows of 72°F at night. Finish your sightseeing early on the 28th (Wed) to allow enough time to drive to Chincoteague Island.

Things to do in Virginia Beach

Outdoors Beaches Parks

Side Trip

Cape Charles Beach
Highlights from your plan
Virginia Beach ©
Virginia Beach
Sandbridge Beach ©
Sandbridge Beach
Military Aviation Museum ©
Military Aviation Museum

3
nights
Chincoteague Island

Chincoteague Island ©
Famous for a wild breed of horses--Chincoteague Ponies--Chincoteague Island embraces the mystery of some of North America’s oldest inhabitants.
Museum of Chincoteague and Tryfan Gallery are good opportunities to explore the local culture. Get in touch with nature at Chincoteague National Wildlife Refuge and Fishing Charters & Tours. There's more to do: get a dose of the wild on a nature and wildlife tour and enjoy the sea views from Assateague Lighthouse.

To find reviews, traveler tips, more things to do, and other tourist information, go to the Chincoteague Island sightseeing planner.

Traveling by car from Virginia Beach to Chincoteague Island takes 2.5 hours. Alternatively, you can take a bus; or take a bus. August in Chincoteague Island sees daily highs of 84°F and lows of 68°F at night. Finish your sightseeing early on the 31st (Sat) so you can drive back home.

Things to do in Chincoteague Island

Wildlife Tours Outdoors

Side Trip

Assateague Lighthouse
Highlights from your plan
Chincoteague National Wildlife Refuge ©
Nature & Wildlife Tours
Fishing Charters & Tours

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