33 days in Virginia Itinerary

33 days in Virginia Itinerary

Created using Inspirock Virginia trip planner

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Route & dates

33 days in Virginia Itinerary

Start: New York City
Fly:  3​h 15​min
1
Arlington
— 3 nights
Drive:  1​h 30​min
2
Winchester
— 3 nights
Drive:  1​h 15​min
3
Luray
— 3 nights
Drive:  1​h 15​min
4
Shenandoah National Park
— 4 nights
Drive:  1​h 15​min
5
Charlottesville
— 4 nights
Drive:  2​h
6
Bedford
— 1 night
Drive:  3​h 15​min
7
Damascus
— 1 night
Drive:  6​h
8
Williamsburg
— 4 nights
Drive:  1​h 15​min
9
Virginia Beach
— 4 nights
Drive:  2​h 30​min
10
Chincoteague Island
— 4 nights
Drive:  5​h 15​min
End: New York City

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.
Explore the numerous day-trip ideas around Arlington: Steven F. Udvar-Hazy Center (in Chantilly), iFLY Indoor Skydiving - Loudoun (in Ashburn) and National Museum of the Marine Corps (in Triangle). There's much more to do: steep yourself in history at Arlington National Cemetery, appreciate the extensive heritage of Tomb of the Unknowns, pause for some photo ops at U.S. Marine Corps War Memorial, and explore the landscape on two wheels at Mount Vernon Trail.

For other places to visit, reviews, where to stay, and tourist information, use the Arlington trip planner .

New York City to Arlington is an approximately 3.5-hour flight. You can also do a combination of bus and flight; or drive. In July, daily temperatures in Arlington can reach 89°F, while at night they dip to 73°F. Finish up your sightseeing early on the 4th (Thu) so you can go by car to Winchester.

Things to do in Arlington

Historic Sites Parks Museums

Side Trips

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

3
nights
Winchester

Winchester ©
Winchester is an independent city located in the northwestern portion of the Commonwealth of Virginia. Venture out of the city with trips to Hartland Family Orchard (in Markham) and Shenandoah Valley Golf Club (in Front Royal). There's much more to do: admire all the interesting features of Rocking S Ranch, experience rural life at Long Branch Plantation, examine the collection at Shenandoah Valley Civil War Museum, and take in the dramatic scenery at Cascade Falls.

For where to stay, traveler tips, and other tourist information, you can read our Winchester tour website .

You can drive from Arlington to Winchester in 1.5 hours. Other options are to take a bus; or take a train. Traveling from Arlington in July, you can expect nighttime temperatures to be slightly colder in Winchester, with lows of 65°F. Finish your sightseeing early on the 7th (Sun) so you can drive to Luray.

Things to do in Winchester

Museums Golf Outdoors

Side Trips

Long Branch Plantation, Cascade Falls, My Neighbor and Me, Hartland Family Orchard, Shenandoah Valley Golf Club
Highlights from your plan
Rocking S Ranch ©
Rocking S Ranch
Cascade Falls ©
Cascade Falls
Stonewall Jackson's Headquarters ©
Stonewall Jackson's Headquarters

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.
Luray is known for nature, museums, trails, zoos & aquariums, and adventure. Your plan includes some of its best attractions: explore the stunning scenery at Luray Caverns, take in nature's colorful creations at Birdsong Pleasure Garden, stroll through Shenandoah River State Park, and get engrossed in the history at The Car and Carriage Caravan Museum.

To see traveler tips, more things to do, other places to visit, and other tourist information, read our Luray travel planner .

Traveling by car from Winchester to Luray takes 1.5 hours. In July in Luray, expect temperatures between 86°F during the day and 66°F at night. Finish up your sightseeing early on the 10th (Wed) so you can go by car to Shenandoah National Park.

Things to do in Luray

Parks Outdoors Trails

Side Trips

Shenandoah River State Park, Shenandoah Caverns, Copper Fox Distillery
Highlights from your plan
Luray Caverns ©
Luray Caverns
Stony Man Mountain Overlook ©
Stony Man Mountain Overlook
The Car and Carriage Caravan Museum ©

4
nights
Shenandoah National Park

Shenandoah National Park ©
Shenandoah National Park showcases a particularly scenic section of Virginia's Blue Ridge Mountains.
You'll find plenty of places to visit near Shenandoah National Park: Vietnam War Foundation Museum (in Ruckersville), Massanutten Indoor WaterPark (in McGaheysville) and Grand Caverns (in Grottoes). Next up on the itinerary: cruise along Skyline Drive, take in the dramatic scenery at Dark Hollow Falls, stroll through Appalachian Trail, and hike along Old Rag Mountain Hike.

To find reviews, photos, more things to do, and other tourist information, you can read our Shenandoah National Park road trip planning tool .

Traveling by car from Luray to Shenandoah National Park takes 1.5 hours. Expect a daytime high around 88°F in July, and nighttime lows around 68°F. Finish your sightseeing early on the 14th (Sun) so you can drive to Charlottesville.

Things to do in Shenandoah National Park

Parks Nature Outdoors

Side Trips

Grand Caverns, Massanutten Indoor WaterPark, Vietnam War Foundation Museum
Highlights from your plan
Appalachian Trail ©
Appalachian Trail
Skyline Drive ©
Skyline Drive
Old Rag Mountain Hike ©
Old Rag Mountain Hike

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.
Change things up with these side-trips from Charlottesville: Lexington (Virginia Military Institute, Lee Chapel and Museum, & more) and Natural Bridge (The Natural Bridge of Virginia & Virginia Safari Park). There's much more to do: explore the galleries of Thomas Jefferson's Monticello, gain insight at University of Virginia, steep yourself in history at The Glass Palette - Interactive Glass Art Studio, and indulge your taste buds at Food & Drink.

To find traveler tips and tourist information, read Charlottesville online trip itinerary builder .

Traveling by car from Shenandoah National Park to Charlottesville takes 1.5 hours. Alternatively, you can do a combination of taxi and bus. In July, plan for daily highs up to 88°F, and evening lows to 68°F. Finish up your sightseeing early on the 18th (Thu) so you can travel to Bedford.

Things to do in Charlottesville

Parks Historic Sites Wildlife

Side Trips

Lexington, Natural Bridge
Highlights from your plan
Monticello ©
Monticello
Virginia Safari Park ©
Virginia Safari Park
Natural Bridge State Park ©
Natural Bridge State Park

1
night
Bedford

Bedford ©
Bedford is an incorporated town and former independent city located within Bedford County in the U.S. On the 19th (Fri), see the interesting displays at Bedford Museum & Genealogical Library, appreciate the history behind National D-Day Memorial, then admire the landmark architecture of Thomas Jefferson's Poplar Forest, and finally appreciate the extensive heritage of Historic Centertown Bedford.

To find other places to visit, more things to do, reviews, and tourist information, go to the Bedford trip itinerary builder app .

Getting from Charlottesville to Bedford by car takes about 2 hours. In July, daytime highs in Bedford are 86°F, while nighttime lows are 66°F. Wrap up your sightseeing on the 19th (Fri) to allow time to travel to Damascus.

Things to do in Bedford

Neighborhoods Historic Sites Museums

Side Trip

Thomas Jefferson's Poplar Forest
Highlights from your plan
National D-Day Memorial ©
National D-Day Memorial
Thomas Jefferson's Poplar Forest ©
Thomas Jefferson's Poplar Forest
Bedford Museum & Genealogical Library ©

1
night
Damascus

Damascus ©
Damascus is a town in Washington County, Virginia, United States. Start off your visit on the 20th (Sat): hike along Virginia Creeper Trail, then tour the pleasant surroundings at Adventure Damascus, and then join in the after-dark buzz at Damascus Brewery.

To see traveler tips, ratings, other places to visit, and tourist information, use the Damascus trip itinerary planner .

You can drive from Bedford to Damascus in 3 hours. In July, plan for daily highs up to 84°F, and evening lows to 66°F. Finish up your sightseeing early on the 20th (Sat) so you can travel to Williamsburg.

Things to do in Damascus

Parks Trails Outdoors
Highlights from your plan
Damascus Brewery ©
Damascus Brewery

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.
Venture out of the city with trips to St. Luke's Historic Church & Museum (in Smithfield), 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 21st (Sun) at Busch Gardens Williamsburg. Plan for a day of cool, family-friendly fun on the 24th (Wed) at Water Country USA. The adventure continues: make a trip to Colonial Williamsburg, contemplate the long history of Historic Jamestowne, explore and take pictures at College of William & Mary, and pause for some serene contemplation at Bruton Parish Episcopal Church.

To find where to stay, reviews, traveler tips, and more tourist information, refer to the Williamsburg road trip website .

You can drive from Damascus to Williamsburg in 5.5 hours. Another option is to fly. Prepare for a bit warmer weather when traveling from Damascus in July: high temperatures in Williamsburg hover around 91°F and lows are around 73°F. Cap off your sightseeing on the 25th (Thu) early enough to go by car to Virginia Beach.

Things to do in Williamsburg

Theme Parks Historic Sites Museums

Side Trips

The Mariners' Museum & Park, Virginia Museum of Fine Arts, St. Luke's Historic Church & Museum
Highlights from your plan
Busch Gardens Williamsburg ©
Busch Gardens Williamsburg
Colonial Williamsburg ©
Colonial Williamsburg
Historic Jamestowne ©
Historic Jamestowne

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.
Virginia Beach is known for beaches, childrens museums, museums, adventure, and historic sites. Your plan includes some of its best attractions: take in the waterfront at Virginia Beach Boardwalk, tour the pleasant surroundings at Sandbridge Beach, glide through the air with a parasailing or paragliding tour, and kick back and relax at Virginia Beach.

To find where to stay, maps, and other tourist information, refer to the Virginia Beach day trip planning app .

Traveling by car from Williamsburg to Virginia Beach takes 1.5 hours. Alternatively, you can take a bus; or take a bus. July in Virginia Beach sees daily highs of 89°F and lows of 73°F at night. Finish up your sightseeing early on the 29th (Mon) so you can go by car to Chincoteague Island.

Things to do in Virginia Beach

Outdoors Parks Museums

Side Trip

Norfolk
Highlights from your plan
Virginia Beach ©
Virginia Beach
Virginia Beach Boardwalk ©
Virginia Beach Boardwalk

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 30th (Tue) exploring nature at Chincoteague National Wildlife Refuge. The adventure continues: surround yourself with nature on a nature and wildlife tour, take in the exciting artwork at Tryfan Gallery, get outside with Donald J. Leonard, and stop by MamerSass.

To see reviews, traveler tips, where to stay, and more tourist information, read our Chincoteague Island trip planner .

You can drive from Virginia Beach to Chincoteague Island in 2.5 hours. Alternatively, you can take a bus; or take a bus. July in Chincoteague Island sees daily highs of 86°F and lows of 72°F at night. Finish up your sightseeing early on the 2nd (Fri) so you can go by car back home.

Things to do in Chincoteague Island

Wildlife Outdoors Parks

Side Trips

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

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