60 days in Virginia Itinerary

60 days in Virginia Itinerary

Created using Inspirock Virginia trip planner

Make it your trip
Drive
1
Chincoteague Island
— 6 nights
Drive
2
Virginia Beach
— 8 nights
Drive
3
Williamsburg
— 9 nights
Drive
4
Charlottesville
— 7 nights
Drive
5
Roanoke
— 7 nights
Drive
6
Shenandoah National Park
— 7 nights
Drive
7
Luray
— 7 nights
Drive
8
Arlington
— 8 nights
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Chincoteague Island

— 6 nights
Famous for a wild breed of horses--Chincoteague Ponies--Chincoteague Island embraces the mystery of some of North America’s oldest inhabitants.
Satisfy your inner culture vulture at Chincoteague Bay Field Station and Museum of Chincoteague. You'll explore and learn at Tryfan Gallery and Beebe Ranch. You'll find plenty of places to visit near Chincoteague Island: Onancock (Ker Place & Hopkins & Bros. Store). Spend the 28th (Tue) exploring nature at Chincoteague National Wildlife Refuge. The adventure continues: get a dose of the wild on a nature and wildlife tour, have some family-friendly fun at Surfside Golf, let little ones run wild at Chincoteague Veteran's Memorial Park, and browse the collection at Chincoteague Island Library.

To see other places to visit, maps, and more tourist information, refer to the Chincoteague Island vacation app.

Washington DC to Chincoteague Island is an approximately 3.5-hour car ride. You can also do a combination of train, bus, and taxi; or take a bus. In May, daily temperatures in Chincoteague Island can reach 72°F, while at night they dip to 57°F. Wrap up your sightseeing on the 2nd (Sun) to allow time to drive to Virginia Beach.

Things to do in Chincoteague Island

Wildlife · Outdoors · Parks · Nature

Side Trips

Virginia Beach

— 8 nights

The Resort City

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.
Kids will enjoy Virginia Beach and Sandbridge Beach. Cape Henry Lighthouse and Virginia Beach Law Enforcement Memorial will appeal to history buffs. Explore Virginia Beach's surroundings by going to Chatham Vineyards (in Machipongo), Hampton (Buckroe Beach and Park & Fort Monroe's Casemate Museum) and The Chrysler Museum Glass Studio (in Norfolk). And it doesn't end there: take a leisurely stroll along Virginia Beach Boardwalk, immerse yourself in nature at First Landing State Park, examine the collection at Military Aviation Museum, and explore the world behind art at Chrysler Museum of Art.

For traveler tips, where to stay, and more tourist information, read our Virginia Beach trip 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. In June in Virginia Beach, expect temperatures between 85°F during the day and 69°F at night. Wrap up your sightseeing on the 10th (Mon) early enough to drive to Williamsburg.

Things to do in Virginia Beach

Parks · Museums · Outdoors · Beaches

Side Trips

Williamsburg

— 9 nights

Colonial Capital

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 St. Luke's Historic Church & Museum. Deepen your sense of the past at sights like Historic Jamestowne and Jamestown Settlement. You'll find plenty of places to visit near Williamsburg: Mattaponi Springs Golf Club (in Ruther Glen), Blandford Church and Cemetery (in Petersburg) and North Anna Battlefield Park (in Ashland). Plan for a day of cool, family-friendly fun on the 14th (Fri) at Busch Gardens Williamsburg. Plan for a day of cool, family-friendly fun on the 16th (Sun) at Water Country USA. There's still lots to do: admire the masterpieces at Virginia Museum of Fine Arts, get engrossed in the history at Colonial Williamsburg Wetherburn Tavern, contemplate the long history of George Wythe House, and stroll the grounds of Hollywood Cemetery.

For where to stay, more things to do, maps, and tourist information, go to the Williamsburg trip builder tool.

Getting from Virginia Beach to Williamsburg by car takes about 1.5 hours. Other options: take a bus; or do a combination of bus and train. In June, plan for daily highs up to 87°F, and evening lows to 68°F. Wrap up your sightseeing on the 19th (Wed) early enough to drive to Charlottesville.

Things to do in Williamsburg

Historic Sites · Theme Parks · Museums · Outdoors

Side Trips

Charlottesville

— 7 nights

Hoo-Ville

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.
Visit Monticello and McLean House for their historical value. Do some cultural sightseeing at James Madison's Montpelier and Appomattox Court House National Historical Park. You'll find plenty of places to visit near Charlottesville: Orange (St. Thomas Parish Church & Finders Keepers), Loose Shoe Brewing Company (in Amherst) and Cooper Vineyards (in Louisa). There's still lots to do: steep yourself in history at Woodrow Wilson Birthplace, do a tasting at King Family Vineyards, brush up on your knowledge of spirits at Ragged Branch Distillery, and don't miss a visit to Patrick Henry's Scotchtown.

To see where to stay, maps, and tourist information, refer to the Charlottesville trip itinerary builder site.

Traveling by car from Williamsburg to Charlottesville takes 2.5 hours. Alternatively, you can take a bus; or do a combination of train and bus. In June, plan for daily highs up to 84°F, and evening lows to 64°F. Finish up your sightseeing early on the 26th (Wed) so you can go by car to Roanoke.

Things to do in Charlottesville

Wineries · Historic Sites · Breweries & Distilleries · Shopping

Side Trips

Roanoke

— 7 nights
Roanoke is an independent city in the U.S. Get some historical perspective at Natural Bridge State Park and St. John's Episcopal Church. Your cultural itinerary includes sights like Sinking Creek Covered Bridge and Bedford Museum & Genealogical Library. Explore Roanoke's surroundings by going to Natural Bridge (Virginia Safari Park, Dinosaur Kingdom II, &more), Hickory Hill Vineyards (in Moneta) and Villa Appalaccia Winery (in Floyd). There's still lots to do: play a few rounds at Olde Mill Golf Resort, gain insight at Virginia Military Institute, indulge your thirst for a good beer at Deschutes Brewery Tasting Room, and raise your glass at The Flying Mouse Brewery.

To find reviews, more things to do, ratings, and more tourist information, refer to the Roanoke driving holiday planning site.

Traveling by car from Charlottesville to Roanoke takes 2.5 hours. Alternatively, you can take a bus; or take a train. In June, plan for daily highs up to 84°F, and evening lows to 64°F. Wrap up your sightseeing on the 3rd (Wed) early enough to drive to Shenandoah National Park.

Things to do in Roanoke

Parks · Wineries · Breweries & Distilleries · Nature

Side Trips

Shenandoah National Park

— 7 nights
Shenandoah National Park showcases a particularly scenic section of Virginia's Blue Ridge Mountains.
You'll visit kid-friendly attractions like Old Rag Mountain Hike and Skyline Drive. Let the collections at Brownsburg Museum and Harrisonburg Fire Department Museum capture your imagination. Explore Shenandoah National Park's surroundings by going to White Hall Vineyards (in Crozet), Moss Vineyards (in Dyke) and McGaheysville (Brix and Columns Vineyards & Zipline). There's still lots to do: hike along Appalachian Trail, do a tasting at Barren Ridge Vineyards, take in the history at McDowell Battlefield, and explore the engaging exhibits at Explore More Discovery Museum.

To find where to stay, maps, other places to visit, and tourist information, use the Shenandoah National Park online day trip planner.

You can drive from Roanoke to Shenandoah National Park in 2.5 hours. Alternatively, you can do a combination of bus and taxi; or do a combination of train and taxi. In July in Shenandoah National Park, expect temperatures between 88°F during the day and 68°F at night. Finish your sightseeing early on the 10th (Wed) so you can drive to Luray.

Things to do in Shenandoah National Park

Wineries · Outdoors · Parks · Nature

Side Trips

Luray

— 7 nights

Cabin Capital of Virginia

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.
Get some cultural insight at Trinity Episcopal Church and Cooter's in the Country. Let the collections at Shenandoah Valley Cultural Heritage Museum at The Edinburg Mill and Cooter's in Luray capture your imagination. Explore the numerous day-trip ideas around Luray: Massanutten Indoor WaterPark (in Massanutten), Vintage Ridge Vineyard (in Rectortown) and Delaplane (RdV Vineyards, Barrel Oak Winery, &more). The adventure continues: explore the stunning scenery at Luray Caverns, brush up on your knowledge of spirits at Copper Fox Distillery, make a trip to The Yellow Barn at Shenandoah Caverns, and hike along Stony Man Mountain Overlook.

To find ratings, reviews, traveler tips, and tourist information, you can read our Luray day trip site.

Traveling by car from Shenandoah National Park to Luray takes 1.5 hours. In July, plan for daily highs up to 86°F, and evening lows to 66°F. Finish up your sightseeing early on the 17th (Wed) so you can go by car to Arlington.

Things to do in Luray

Wineries · Parks · Museums · Nature

Side Trips

Arlington

— 8 nights

National History, Local Flavor

Located just across the Potomac River from Washington, D.C., the county of Arlington blends big city and sprawling suburban environments.
Do some cultural sightseeing at Arlington National Cemetery and Steven F. Udvar-Hazy Center. Museum-lovers will get to explore George Washington's Mount Vernon and Cold War Museum. Explore Arlington's surroundings by going to Manassas (KO Distilling & Manassas National Battlefield Park), National Museum of the Marine Corps (in Triangle) and Oak Crest Vineyard and Winery (in King George). There's much more to do: get to know the fascinating history of The Tomb of the Unknown Soldier, take an in-depth tour of Woodlawn & Pope-Leighey House, pause for some photo ops at U.S. Marine Corps War Memorial, and explore the world behind art at Museum of the Shenandoah Valley.

To see maps, other places to visit, more things to do, and other tourist information, refer to the Arlington trip planner.

You can drive from Luray to Arlington in 2 hours. Alternatively, you can do a combination of taxi and bus; or fly. Traveling from Luray in July, Arlington is somewhat warmer at night with lows of 73°F. Wrap up your sightseeing on the 25th (Thu) early enough to drive back home.

Things to do in Arlington

Museums · Historic Sites · Wineries · Outdoors

Side Trips

Virginia travel guide

4.6
Historic Sites · Wineries & Vineyards · Specialty Museums
Old Dominion
The home of the first permanent English colony in the New World, Virginia is a prime holiday destination for those looking to immerse themselves in American heritage. Proud of its colorful history, distinct culture, and southern drawl, Virginians see their state as the place where the imaginary line between the north and the south is drawn. With scenic beauties as diverse as its people, Virginia is a land of rolling hills, rugged mountains, lush valleys, dense forests, and secluded beaches along picturesque bays. Bordered on the east by the Atlantic and the west by the Appalachian Mountains, with rolling farmland in the middle, the state offers countless places to visit for history buffs, nature lovers, and passionate foodies.