31 days in Capital Region USA Itinerary

31 days in Capital Region USA Itinerary

Created using Inspirock Capital Region USA tour itinerary builder

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Route & dates

31 days in Capital Region USA Itinerary

Start: Chennai
Fly:  22​h 45​min
1
Washington DC
— 6 nights
Drive:  1​h 30​min
2
Winchester
— 4 nights
Drive:  2​h 15​min
3
Charlottesville
— 4 nights
Drive:  3​h 45​min
4
Damascus
— 2 nights
Drive:  5​h 30​min
5
Williamsburg
— 5 nights
Drive:  3​h
6
Chincoteague Island
— 3 nights
Drive:  2​h 30​min
7
Virginia Beach
— 5 nights
Fly:  26​h
End: Chennai

6
nights
Washington DC

Washington DC ©
The capital of the United States, the District of Columbia contains the lion's share of the country's most treasured monuments, memorials, and public museums.
Go for a jaunt from Washington DC to Baltimore to see Horseshoe Casino about 1 hour away. There's still lots to do: examine the collection at National Air and Space Museum, learn more about the world around you at Smithsonian National Museum of Natural History, get a sense of history and politics at White House, and get your bearings at Library of Congress.

To see traveler tips, reviews, ratings, and other tourist information, use the Washington DC day trip planning tool .

Chennai, India to Washington DC is an approximately 23-hour flight. You can also do a combination of flight and train; or do a combination of flight and train. Due to the time zone difference, you'll gain 10 hours traveling from Chennai to Washington DC. In May, Washington DC is much colder than Chennai - with highs of 28°C and lows of 17°C. Wrap up your sightseeing on the 8th (Fri) early enough to drive to Winchester.

Things to do in Washington DC

Museums Historic Sites Parks

Side Trips

Arlington, Horseshoe Casino
Highlights from your plan
National Air and Space Museum ©
National Air and Space Museum
National Gallery of Art ©
National Gallery of Art

4
nights
Winchester

Winchester ©
Winchester is an independent city located in the northwestern portion of the Commonwealth of Virginia. You'll find plenty of places to visit near Winchester: Cumberland (Great Allegheny Passage & Charis Winery), Luray Caverns (in Luray) and Copper Fox Distillery (in Sperryville). There's much more to do: wander the wide-open spaces of Rocking S Ranch, admire the sheer force of Cascade Falls, don't miss a visit to Handley Regional Library, and stop by Marker-Miller Orchards.

To find reviews, where to stay, photos, and more tourist information, read our Winchester visit planning app .

Drive from Washington DC to Winchester in 1.5 hours. Alternatively, you can take a train; or take a bus. Expect slightly colder evenings in Winchester when traveling from Washington DC in May, with lows around 13°C. Wrap up your sightseeing on the 12th (Tue) to allow time to drive to Charlottesville.

Things to do in Winchester

Parks Nature Historic Sites

Side Trips

Cumberland, Antietam National Battlefield, National Shrine Grotto of Lourdes, Just Lookin, Copper Fox Distillery
Highlights from your plan
Rocking S Ranch ©
Rocking S Ranch
Antietam National Battlefield ©
Antietam National Battlefield
Luray Caverns ©
Luray Caverns

4
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.
You'll find plenty of places to visit near Charlottesville: National D-Day Memorial (in Bedford), Stony Man Mountain Overlook (in Luray) and Virginia Military Institute (in Lexington). Next up on the itinerary: steep yourself in history at Monticello, explore the world behind art at Jefferson School African American Heritage Center, view the masterpieces at C'ville Arts: A Cooperative Gallery, and gain insight at The Glass Palette - Interactive Glass Art Studio.

To find maps, ratings, photos, and tourist information, use the Charlottesville travel planning tool .

You can drive from Winchester to Charlottesville in 2.5 hours. Alternatively, you can do a combination of bus and flight; or take a train. In May, daytime highs in Charlottesville are 28°C, while nighttime lows are 15°C. Finish your sightseeing early on the 16th (Sat) so you can travel to Damascus.

Things to do in Charlottesville

Parks Outdoors Scenic Drive

Side Trips

Shenandoah National Park, National D-Day Memorial, Brownsburg Museum, Virginia Military Institute, Stony Man Mountain Overlook
Highlights from your plan
National D-Day Memorial ©
National D-Day Memorial
Monticello ©
Monticello
Old Rag Mountain Hike ©
Old Rag Mountain Hike

2
nights
Damascus

Damascus ©
Damascus is a town in Washington County, Virginia, United States. Start off your visit on the 17th (Sun): immerse yourself in nature at Grayson Highlands State Park, tour the pleasant surroundings at Appalachian Trail, and then trek along Virginia Creeper National Recreation Trail. On the 18th (Mon), you'll have a packed day of sightseeing: examine the collection at Star Museum, see the interesting displays at Fields-Penn 1860 House Museum, and then ride a horse along Virginia Creeper Trail Club.

To see reviews, photos, more things to do, and other tourist information, refer to the Damascus trip itinerary maker app .

You can drive from Charlottesville to Damascus in 4 hours. Another option is to do a combination of car and flight. In May, daily temperatures in Damascus can reach 28°C, while at night they dip to 14°C. Wrap up your sightseeing on the 18th (Mon) early enough to travel to Williamsburg.

Things to do in Damascus

Parks Trails Outdoors

Side Trips

Abingdon, Grayson Highlands State Park, Appalachian Trail
Highlights from your plan
Grayson Highlands State Park ©
Grayson Highlands State Park
Fields-Penn 1860 House Museum ©
Fields-Penn 1860 House Museum

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.
You'll find plenty of places to visit near Williamsburg: Room Escape Games (in Henrico), Richmond (Maymont, Virginia Museum of Fine Arts, & more) and The Mariners' Museum & Park (in Newport News). There's much more to do: steep yourself in history at Colonial Williamsburg, step aboard Jamestown Settlement, take an in-depth tour of Pamplin Historical Park, and take in the spiritual surroundings of St. Luke's Historic Church & Museum.

For maps, where to stay, other places to visit, and other tourist information, read Williamsburg trip itinerary app .

Traveling by car from Damascus to Williamsburg takes 5.5 hours. Alternatively, you can do a combination of car and flight. In May, plan for daily highs up to 30°C, and evening lows to 17°C. Finish up your sightseeing early on the 23rd (Sat) so you can go by car to Chincoteague Island.

Things to do in Williamsburg

Museums Historic Sites Parks

Side Trips

Richmond, Room Escape Games, The Mariners' Museum & Park, St. Luke's Historic Church & Museum, Pamplin Historical Park
Highlights from your plan
St. Luke's Historic Church & Museum ©
Colonial Williamsburg ©
Colonial Williamsburg
Busch Gardens Williamsburg ©
Busch Gardens Williamsburg

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.
Explore the numerous day-trip ideas around Chincoteague Island: Crisfield Heritage Foundation (in Crisfield), Blackwater National Wildlife Refuge (in Cambridge) and Eastern Shore Baseball Hall of Fame Museum (in Salisbury). There's much more to do: explore the wealth of natural beauty at Chincoteague National Wildlife Refuge, look for gifts at MamerSass, get a dose of the wild on a nature and wildlife tour, and see the interesting displays at Chincoteague Bay Field Station.

To see maps, other places to visit, where to stay, and more tourist information, go to the Chincoteague Island road trip planning site .

Traveling by car from Williamsburg to Chincoteague Island takes 3 hours. Alternatively, you can take a bus. When traveling from Williamsburg in May, plan for slightly colder days and about the same nights in Chincoteague Island: temperatures range from 26°C by day to 16°C at night. Finish up your sightseeing early on the 26th (Tue) so you can go by car to Virginia Beach.

Things to do in Chincoteague Island

Wildlife Parks Museums

Side Trips

Eastern Shore Baseball Hall of Fame Museum, Crisfield Heritage Foundation, Blackwater National Wildlife Refuge, Chincoteague Bay Field Station
Highlights from your plan
Chincoteague National Wildlife Refuge ©
Nature & Wildlife Tours
Blackwater National Wildlife Refuge ©

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.
Step out of Virginia Beach with an excursion to Weyanoke Bird and Wildflower Sanctuary in Norfolk--about 38 minutes away. Next up on the itinerary: take in the waterfront at Virginia Beach Boardwalk, take in nature's colorful creations at Norfolk Botanical Garden, sample the fine beverages at Tarnished Truth Distilling Company, and stroll through Sandbridge Beach.

To find other places to visit, where to stay, ratings, and more tourist information, use the Virginia Beach travel route planner .

You can drive from Chincoteague Island to Virginia Beach in 2.5 hours. Other options are to take a bus; or take a bus. May in Virginia Beach sees daily highs of 29°C and lows of 18°C at night. You will have some time to spend on the 31st (Sun) before leaving for home.

Things to do in Virginia Beach

Parks Museums Nature

Side Trip

Norfolk
Highlights from your plan
Tarnished Truth Distilling Company ©
Virginia Beach Boardwalk ©
Virginia Beach Boardwalk
Military Aviation Museum ©
Military Aviation Museum