21 days in Virginia Itinerary

21 days in Virginia Itinerary

Created using Inspirock Virginia travel route planner

Make it your trip
Fly
1
Charlottesville
— 3 nights
Drive
2
Luray
— 2 nights
Drive
3
Fredericksburg
— 3 nights
Drive
4
Williamsburg
— 5 nights
Drive
5
Virginia Beach
— 4 nights
Drive
6
Chincoteague Island
— 3 nights
Drive

S M T W T F S
25
26
27
28
29
30
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22

Charlottesville

— 3 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.
Do some cultural sightseeing at James Madison's Montpelier and Appomattox Court House National Historical Park. Visit James Monroe's Highland and Woodrow Wilson Birthplace for their historical value. Explore Charlottesville's surroundings by going to Frontier Culture Museum (in Staunton) and Lee Chapel and Museum (in Lexington). The adventure continues: gain insight at The Glass Palette - Interactive Glass Art Studio, take in nature's colorful creations at Monticello, admire the landmark architecture of University of Virginia, and stroll through Saunders-Monticello Trail.

To find maps, where to stay, and other tourist information, go to the Charlottesville day trip site.

New York City to Charlottesville is an approximately 4-hour flight. You can also drive; or take a train. When traveling from New York City in May, plan for a bit warmer days in Charlottesville, with highs around 76°F, while nights are about the same with lows around 55°F. Cap off your sightseeing on the 4th (Tue) early enough to go by car to Luray.

Things to do in Charlottesville

Historic Sites · Parks · Museums · Trails

Side Trips

Luray

— 2 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.
Kick off your visit on the 5th (Wed): explore the stunning scenery at Luray Caverns, then stroll through Stony Man Mountain Overlook, and then take in the dramatic scenery at Dark Hollow Falls. Keep things going the next day: see the interesting displays at Shenandoah Caverns, then explore the fascinating underground world of Shenandoah Caverns, and then take an in-depth tour of The Car and Carriage Caravan Museum.

For other places to visit, ratings, more things to do, and more tourist information, read Luray online visit planner.

Traveling by car from Charlottesville to Luray takes 1.5 hours. Alternatively, you can do a combination of bus and taxi. In May, daytime highs in Luray are 75°F, while nighttime lows are 52°F. Cap off your sightseeing on the 6th (Thu) early enough to go by car to Fredericksburg.

Things to do in Luray

Parks · Nature · Museums · Trails

Side Trips

Fredericksburg

— 3 nights
Fredericksburg is an independent city located in the Commonwealth of Virginia in the Eastern United States. National Museum of the Marine Corps and Fredericksburg & Spotsylvania National Military Park are good opportunities to explore the local culture. Your inner history buff will appreciate Chatham Manor and Fredericksburg Battlefield and Visitor Center. There's lots more to do: steep yourself in history at The Rising Sun Tavern, get engrossed in the history at Hugh Mercer Apothecary Shop, take in the history at Chancellorsville Battlefield Visitor Center, and appreciate the extensive heritage of Old Town.

To find traveler tips, more things to do, maps, and other tourist information, refer to the Fredericksburg trip planner.

Drive from Luray to Fredericksburg in 2 hours. Alternatively, you can do a combination of taxi and bus; or do a combination of taxi, bus, and train. In May in Fredericksburg, expect temperatures between 76°F during the day and 56°F at night. Wrap up your sightseeing on the 9th (Sun) early enough to drive to Williamsburg.

Things to do in Fredericksburg

Historic Sites · Museums

Side Trips

Williamsburg

— 5 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.
Get a sense of the local culture at Colonial Williamsburg and Abby Aldrich Rockefeller Folk Art Museum. You'll visit kid-friendly attractions like American Revolution Museum at Yorktown and DeWitt Wallace Decorative Arts Museum. Explore the numerous day-trip ideas around Williamsburg: Berkeley Plantation (in Charles City), St. Luke's Historic Church & Museum (in Smithfield) and The Mariners' Museum & Park (in Newport News). There's much more to do: get a new perspective on things with Boat Tours & Water Sports, pause for some serene contemplation at Bruton Parish Episcopal Church, contemplate the long history of Historic Jamestowne, and get to know the resident critters at Virginia Living Museum.

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

Traveling by car from Fredericksburg to Williamsburg takes 2 hours. Alternatively, you can take a train; or take a bus. May in Williamsburg sees daily highs of 79°F and lows of 59°F at night. Cap off your sightseeing on the 14th (Fri) early enough to go by car to Virginia Beach.

Things to do in Williamsburg

Museums · Historic Sites · Parks · Childrens Museums

Side Trips

Virginia Beach

— 4 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.
Get a sense of the local culture at Military Aviation Museum and White House of the Confederacy. Attractions like Cape Henry Lighthouse and Virginia Beach Surf & Rescue Museum make great kid-friendly stops. Explore Virginia Beach's surroundings by going to Richmond (Shockoe Bottom Clay & Virginia Capitol Building). The adventure continues: admire the masterpieces at Chrysler Museum of Art, immerse yourself in nature at First Landing State Park, enjoy the sand and surf at Sandbridge Beach, and take a pleasant ride with a tour on horseback.

To see other places to visit, traveler tips, maps, and other tourist information, read our Virginia Beach online travel planner.

Traveling by car from Williamsburg to Virginia Beach takes 1.5 hours. Alternatively, you can take a bus; or do a combination of train and bus. In May, daytime highs in Virginia Beach are 77°F, while nighttime lows are 60°F. Finish your sightseeing early on the 18th (Tue) so you can drive to Chincoteague Island.

Things to do in Virginia Beach

Museums · Parks · Historic Sites · Outdoors

Side Trips

Chincoteague Island

— 3 nights
Famous for a wild breed of horses--Chincoteague Ponies--Chincoteague Island embraces the mystery of some of North America’s oldest inhabitants.
Bring the kids along to Boat Tours & Water Sports and Chincoteague National Wildlife Refuge. Your cultural itinerary includes sights like Assateague Lighthouse and Chincoteague Bay Field Station. And it doesn't end there: get engrossed in the history at Museum of Chincoteague, have fun at Chincoteague Veteran's Memorial Park, don't miss a visit to Chincoteague Cultural Alliance, and look for gifts at Pony Tails.

For traveler tips, ratings, other places to visit, and more tourist information, use the Chincoteague Island trip planner.

Getting from Virginia Beach to Chincoteague Island by car takes about 2.5 hours. Other options: take a bus; or take a bus. When traveling from Virginia Beach in May, plan for a bit cooler days in Chincoteague Island, with highs around 72°F, while nights are about the same with lows around 57°F. Finish up your sightseeing early on the 21st (Fri) so you can go by car back home.

Things to do in Chincoteague Island

Parks · Wildlife · Nature · Museums

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.