27 days in Virginia Itinerary

27 days in Virginia Itinerary

Created using Inspirock Virginia travel planner

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Route & dates

27 days in Virginia Itinerary

Start: Richmond
bus:  1​h 15​min
1
Charlottesville
— 2 nights
Drive:  1​h 30​min
2
Luray
— 3 nights
Drive:  1​h 15​min
3
Winchester
— 3 nights
Drive:  1​h 30​min
4
Arlington
— 4 nights
Drive:  3​h 45​min
5
Chincoteague Island
— 4 nights
Drive:  2​h 30​min
6
Virginia Beach
— 4 nights
Drive:  1​h 15​min
7
Williamsburg
— 6 nights
train:  1​h
End: Richmond

2
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.
Step out of Charlottesville to go to Shenandoah National Park and see Old Rag Mountain Hike, which is approximately 1h 05 min away. Spend the 17th (Fri) on a tasty journey with a beer tour and tasting. The adventure continues: take in nature's colorful creations at Monticello, steep yourself in history at Mulberry Row, indulge in some culinary diversions at a local gastronomic tour, and stop by C'ville Arts: A Cooperative Gallery.

To see ratings, other places to visit, maps, and more tourist information, go to the Charlottesville attractions planner.

Richmond to Charlottesville is an approximately 1.5-hour car ride. You can also take a bus. In May, plan for daily highs up to 76°F, and evening lows to 55°F. Finish your sightseeing early on the 17th (Fri) to allow enough time to drive to Luray.

Things to do in Charlottesville

Tours Parks Historic Sites

Side Trip

Old Rag Mountain Hike
Highlights from your plan
Old Rag Mountain Hike ©
Old Rag Mountain Hike
Monticello ©
Monticello
Beer Tastings & Tours

3
nights
Luray

Luray ©
Nestled in the heart of the valley formed by the Shenandoah River, Luray draws visitors with a vast underground cavern system adorned with stalactites, stalagmites, and mirrored pools.
Venture out of the city with trips to Shenandoah National Park (Bearfence Mountain & Appalachian Trail). There's still lots to do: take in breathtaking views at Luray Caverns, cruise along Skyline Drive, brush up on your knowledge of spirits at Copper Fox Distillery, and trek along Stony Man Mountain Hike.

For more things to do, ratings, traveler tips, and more tourist information, you can read our Luray trip itinerary app .

Drive from Charlottesville to Luray in 1.5 hours. Alternatively, you can do a combination of bus and car. In May, daily temperatures in Luray can reach 75°F, while at night they dip to 52°F. Finish up your sightseeing early on the 20th (Mon) so you can go by car to Winchester.

Things to do in Luray

Parks Outdoors Nature

Side Trips

Shenandoah National Park, Copper Fox Distillery
Highlights from your plan
Luray Caverns ©
Luray Caverns
Stony Man Mountain Overlook ©
Stony Man Mountain Overlook
Skyline Drive ©
Skyline Drive

3
nights
Winchester

Winchester ©
Winchester is an independent city located in the northwestern portion of the Commonwealth of Virginia. Change things up with these side-trips from Winchester: Raven Rocks (in Bluemont) and Catoctin Creek Distillery (in Purcellville). And it doesn't end there: explore and take pictures at Rocking S Ranch, do a tasting at Valerie Hill Vineyard & Winery, examine the collection at Virginia Museum of Veiled History, and contemplate the long history of Belle Grove Plantation.

To see where to stay, photos, traveler tips, and tourist information, use the Winchester itinerary planner.

Traveling by car from Luray to Winchester takes 1.5 hours. May in Winchester sees daily highs of 73°F and lows of 52°F at night. Finish your sightseeing early on the 23rd (Thu) so you can drive to Arlington.

Things to do in Winchester

Parks Museums Outdoors

Side Trips

Catoctin Creek Distillery, Belle Grove Plantation, Valerie Hill Vineyard & Winery, Cascade Falls, Raven Rocks
Highlights from your plan
Rocking S Ranch ©
Rocking S Ranch
Cascade Falls ©
Cascade Falls
Museum of the Shenandoah Valley ©
Museum of the Shenandoah Valley

4
nights
Arlington

Arlington ©
Located just across the Potomac River from Washington, D.C., the county of Arlington blends big city and sprawling suburban environments.
Change things up with these side-trips from Arlington: George Washington's Mount Vernon (in Mount Vernon), iFLY Indoor Skydiving - Loudoun (in Ashburn) and National Museum of the Marine Corps (in Triangle). And it doesn't end there: explore the different monuments and memorials at Arlington National Cemetery, examine the collection at Steven F. Udvar-Hazy Center, step off the mainland to explore Theodore Roosevelt Island Park, and get to know the fascinating history of The Tomb of the Unknown Soldier.

To find photos, other places to visit, reviews, and other tourist information, go to the Arlington trip maker site .

Drive from Winchester to Arlington in 1.5 hours. Alternatively, you can take a bus; or take a train. Traveling from Winchester in May, plan for a bit warmer nights in Arlington, with lows around 58°F. Wrap up your sightseeing on the 27th (Mon) to allow time to drive to Chincoteague Island.

Things to do in Arlington

Historic Sites Parks Museums

Side Trips

iFLY Indoor Skydiving - Loudoun, National Museum of the Marine Corps, Manassas National Battlefield Park, Steven F. Udvar-Hazy Center, George Washington's Mount Vernon
Highlights from your plan
Arlington National Cemetery ©
Arlington National Cemetery
The Tomb of the Unknown Soldier ©
The Tomb of the Unknown Soldier
Steven F. Udvar-Hazy Center ©
Steven F. Udvar-Hazy Center

4
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.
Spend the 28th (Tue) exploring nature at Chincoteague National Wildlife Refuge. There's much more to do: surround yourself with nature on a nature and wildlife tour, get outside with Donald J. Leonard, stop by Pony Tails, and don't miss a visit to Chincoteague Cultural Alliance.

To see other places to visit, traveler tips, and tourist information, go to the Chincoteague Island travel itinerary planner .

Drive from Arlington to Chincoteague Island in 4 hours. Alternatively, you can do a combination of flight and bus; or do a combination of bus and taxi. In May, plan for daily highs up to 72°F, and evening lows to 57°F. Finish up your sightseeing early on the 31st (Fri) so you can go by car to Virginia Beach.

Things to do in Chincoteague Island

Wildlife Outdoors Parks

Side Trips

Chincoteague Bay Field Station, Assateague Lighthouse
Highlights from your plan
Chincoteague National Wildlife Refuge ©
Nature & Wildlife Tours
Museum of Chincoteague ©
Museum of Chincoteague

4
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 to go to Norfolk and see Skystar Wheel, which is approximately 36 minutes away. The adventure continues: take a leisurely stroll along Virginia Beach Boardwalk, admire the natural beauty at Norfolk Botanical Garden, get up close and personal with brilliant marine life at Virginia Aquarium & Marine Science Center, and explore and take pictures at Battleship Wisconsin.

To find other places to visit, ratings, and tourist information, go to the Virginia Beach trip itinerary builder .

You can drive from Chincoteague Island to Virginia Beach in 2.5 hours. Alternatively, you can take a bus; or take a bus. In May, daytime highs in Virginia Beach are 77°F, while nighttime lows are 60°F. Wrap up your sightseeing on the 4th (Tue) to allow time to drive to Williamsburg.

Things to do in Virginia Beach

Parks Museums Beaches

Side Trip

Norfolk
Highlights from your plan
Virginia Beach Boardwalk ©
Virginia Beach Boardwalk
Military Aviation Museum ©
Military Aviation Museum

6
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.
Explore Williamsburg's surroundings by going to Smithfield (St. Luke's Historic Church & Museum & Windsor Castle Park), Virginia Museum of Fine Arts (in Richmond) and The Mariners' Museum & Park (in Newport News). Plan for a day of cool, family-friendly fun on the 7th (Fri) at Busch Gardens Williamsburg. Plan for a day of cool, family-friendly fun on the 9th (Sun) at Water Country USA. Next up on the itinerary: contemplate the long history of Colonial Williamsburg, admire the masterpieces at Abby Aldrich Rockefeller Folk Art Museum, take in the architecture and atmosphere at Saint Demetrios Greek Orthodox Church, and step aboard Jamestown Settlement.

For other places to visit, traveler tips, ratings, and more tourist information, read our Williamsburg tour itinerary planner .

You can drive from Virginia Beach to Williamsburg in 1.5 hours. Alternatively, you can take a bus; or take a bus. June in Williamsburg sees daily highs of 87°F and lows of 68°F at night. On the 10th (Mon), wrap the sightseeing up by early afternoon so you can take a train back home.

Things to do in Williamsburg

Theme Parks Historic Sites Museums

Side Trips

Smithfield, The Mariners' Museum & Park, Virginia Museum of Fine Arts
Highlights from your plan
Busch Gardens Williamsburg ©
Busch Gardens Williamsburg
Colonial Williamsburg ©
Colonial Williamsburg
Historic Jamestowne ©
Historic Jamestowne

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