An overlook along Skyline Drive in Shenandoah National Park. The road runs the length of the park and every overlook is a different mountain view.
Virginia With Kids Family Travel Guide
“Colonial history two hours from mountain overlooks two hours from a beach boardwalk, and none of it fights for the same week.”
Nicole Damiano, ASTA Verified Travel Advisor with FG Luxury Travel
How many days for Williamsburg?
Four. Two for Colonial Williamsburg itself, one split between Jamestown and Yorktown, and one for Busch Gardens or Water Country. Kids hit a history wall after two straight days, so put the theme park in the middle.
Is Colonial Williamsburg good for younger kids?
Yes, and better than most historic sites. Rent a costume at the visitor center, join the militia muster, watch the trades, and let them run the green. The daily kids' programs are built for ages five to twelve. Teens do better with the evening ghost walks and the courthouse trial.
Shenandoah or the coast?
Shenandoah for short hikes, waterfalls, deer at the roadside and Luray Caverns, ninety minutes from Washington. The coast for Virginia Beach's boardwalk, the aquarium and the Chincoteague ponies. Williamsburg sits between them, so a ten day loop does all three.
When do the Chincoteague ponies swim?
The last Wednesday in July, with the foal auction the next day. It is crowded and it is a real event. The ponies are there all year on Assateague and the boat tours from Chincoteague see them any month.
When should we go?
April, May, September and October for the best weather everywhere. Summer is hot and humid but the beach and the water park make it work. October on Skyline Drive for color is packed on weekends. December in Williamsburg for the Grand Illumination is a family tradition worth planning.
Nicole’s Perspective
Why families hire me for Virginia

Virginia is the state I plan for families who want the founding era without a flight. A meaningful slice of the families I plan for are within a tank of gas of it, and Loudoun County’s wine country markets itself hard to the same DC-metro parents I talk to every week. I taught the colonial period for eight years before I priced my first trip, and Williamsburg in its 250th anniversary year is the version of that lesson I would pick for a ten year old.
Everything below is checked against the park service, the ticket office and the county tourism board directly, not pulled from an old blog post. The prices are this season’s, and the one piece of routing advice I give every client is the same one I give you. Pick one region and do it properly.
Beyond the Bookshelf
A shelf of Virginia stories, the movies that put Hidden Figures and Remember the Titans on the map, and the musicians who grew up there for the drive.
- The Known WorldEdward P. Jones
- Big Stone GapAdriana Trigiani
- Wish You WellDavid Baldacci
- Prodigal SummerBarbara Kingsolver
- The Wettest County in the WorldMatt Bondurant
- ChesapeakeJames A. Michener
- Misty of ChincoteagueMarguerite Henry
- Bridge to TerabithiaKatherine Paterson
- The WandererSharon Creech
- O Is for Old DominionPamela Duncan Edwards
- Good Night VirginiaAdam Gamble
- The Virginia HousewifeMary Randolph
- Virginia Hospitality
- The Colonial Williamsburg Tavern Cookbook
- VictualsRonni Lundy
- Moon Virginia & Maryland
- Backroads of VirginiaBill Lohmann
- DK Eyewitness Washington DC
- Virginia: A HistoryDorothy M. Scobe
- Virginia’s Blue RidgeNancy D. Smith
Book links go to Bookshop.org, which supports local bookstores. Film and music links go to JustWatch and Spotify. As an affiliate we may earn from qualifying purchases.
Why this state, for this family
Why Virginia works with kids
Poppy marks the family parts. Wherever you see her, that section is written for traveling with children.I taught the colonial period for eight years before I priced my first trip, and Virginia is where I send families who want the founding era without a flight. Nothing in the state is more than four hours from Washington, and the trick is picking one region and doing it properly.
A living history town, not a museum with actors
Colonial Williamsburg stays in character, the trade shops make things, and the town itself is the exhibit. In the 250th year it is the version of my old lesson I would pick for a ten year old.
A road that runs the length of a national park
Skyline Drive, 105 miles, over seventy overlooks, thirty dollars a car for a week, and rocks to scramble at Hawksbill. Two hours from the capital.
Wild ponies on a marsh
Chincoteague ponies graze along Beach Road most evenings for ten dollars a car, and the last week of July they swim the channel. The Eastern Shore is the quiet beach nobody plans.
The map
Virginia, Place by Place
This is how I plan things to do in Virginia with kids. Six regions, and they do not overlap much. Coastal Virginia Beach is a beach week. Richmond and Williamsburg are a history week. Shenandoah is a mountain week. Loudoun is a long weekend, not a full trip on its own.




State song Our Great Virginia, adopted in 2015 to the tune of Shenandoah, after the old song was retired for its lyrics. Good to know Eastern time. Sales tax about five to six percent. Virginia is for lovers, says the sign, and it has been saying it since 1969.
Williamsburg
Richmond
Shenandoah
Virginia Beach
Charlottesville
Loudoun Wine Country
Alexandria & Mount Vernon
Virginia’s Eastern Shore
Virginia Is Where Four Presidents Lived and a War Ended
Jamestown, Williamsburg, Yorktown, Monticello, Mount Vernon and Appomattox. More of the country’s founding and its undoing happened here than in any other state.
The Historic Triangle. Jamestown where it started in 1607, Williamsburg where the colony grew up, Yorktown where the Revolution ended. All within twenty minutes of each other and one ticket covers Jamestown and Yorktown together.
Two presidents’ houses an hour apart. Monticello, Jefferson’s house on the hill outside Charlottesville, and Mount Vernon, Washington’s farm on the Potomac. Both sell timed tickets and both tell the story of the enslaved people who ran them, which they did not always.
Richmond was the capital of the Confederacy. The American Civil War Museum at Tredegar tells it from all sides, and Appomattox, where Lee surrendered, is a quiet village two hours west. Older children get it.
Hidden Figures happened in Hampton. The women who did the maths for the space program worked at NASA Langley, and the Virginia Air and Space Science Center in Hampton has the Apollo 12 capsule. A good film to watch before you go.
The Chesapeake is a working bay. Blue crabs, oysters, watermen and the skipjacks. Tangier Island in the middle of it still speaks with a colonial accent and the ferry from Onancock is the strangest day out in the state.
What to Eat in Virginia
Ham, crab and peanuts. Virginia food is old and it is specific.
A Cheese Shop sandwich in Williamsburg. Merchants Square, eleven to fifteen dollars, with the house dressing on it. Eat it on a bench outside and buy a bottle of the dressing for home.
Blue crab, picked at a paper table. Steamed with Old Bay, hammered open with a mallet on the Northern Neck or the Eastern Shore. Messy, slow and the meal children remember.
Virginia ham on a biscuit. Salt cured Smithfield ham, sliced thin on a small biscuit. Sold at every country store and the correct road snack between regions.
Brunswick stew and peanut soup. The stew is a Virginia argument with Georgia, and peanut soup is served at the King’s Arms in Williamsburg the colonial way. Both work for a child who likes soup.
Apples and cider in Shenandoah. Roadside orchards along Route 340 in September and October, cider doughnuts, and the pick your own farms outside Charlottesville.
Getting Around Virginia
Four hours from Washington to everything, and the car is the whole plan outside the capital.
Drive from Washington, or fly to Richmond or Norfolk. Dulles and Reagan for the DC corridor, Richmond for Williamsburg, Norfolk for the beach and the Eastern Shore. Direct flights from most of the country.
Amtrak reaches Williamsburg. The Northeast Regional runs Washington to Richmond to Williamsburg and on to Newport News. Park once in Williamsburg and walk everything.
Interstate 95 is the worst road in the state. Washington to Richmond can take two hours or four. Leave early, or take the train, and never plan the Friday afternoon drive south.
Skyline Drive is 35 miles an hour. 105 miles end to end, enforced, and three or four hours with stops. Enter at Front Royal or Thornton Gap and do a section, not the whole thing.
The Bridge Tunnel is a toll and an event. 17.6 miles across the bay from Virginia Beach to the Eastern Shore, underwater twice, with a rest stop on an island in the middle. Children rate it above most attractions.

Hawksbill, the high point of Shenandoah, a short steep trail and rocks at the top.
Money and Practical Basics
Virginia is a cheap history state with timed tickets that sell out.
Williamsburg is the ticket. About 37.50 an adult and 10 for ages six to twelve for a single day, more for multi day. Jamestown and Yorktown together on a separate combination ticket. Book ahead in the 250th year.
Monticello and Mount Vernon are timed. Monticello’s house tour is about 42 an adult and a few dollars for children, Mount Vernon similar. Summer slots sell out, so book with the hotel.
Shenandoah is thirty dollars a car and not on the surcharge list. A week’s pass, no international surcharge, and the Blue Ridge Parkway south of it is free.
The beach is free, the parking is not. Virginia Beach sand and the boardwalk cost nothing. Parking near the boardwalk in summer runs real money. A hotel with parking included is worth the difference.
Sales tax at just over five percent. Lower than most states, hotel taxes on top, and tipping at eighteen to twenty in a sit down restaurant.
When To Go
Virginia has four real seasons and each region peaks differently. Fall foliage and summer beach weeks are not the same trip and should not be planned the same way.
Mid-October is peak leaf season
Skyline Drive gets seriously crowded the second and third weekends of October. Go on a weekday or book Williamsburg instead that week.
June through August for the beach
Virginia Beach’s water is swimmable and the boardwalk is in full season. It is also the most humid stretch for Williamsburg and Richmond, so plan indoor breaks.
April and May for Williamsburg
Mild temperatures, gardens in bloom, and school groups mostly gone by late May. This is the best window for a history-heavy week with younger kids.
How Many Days & First-Trip Routing
How many days for Williamsburg? Four.
Two for Colonial Williamsburg itself, one split between Jamestown and Yorktown, and one for Busch Gardens or Water Country.
Kids hit a history wall after two straight days, so put the theme park in the middle.
How to Route a Virginia Week
Four regions that do not overlap, and the one piece of advice I give every client is the same. Pick one.
The history week. Williamsburg as the base, Jamestown and Yorktown as days, Richmond on the way in or out. Three to four hours from Washington by car or train.
The beach week. Virginia Beach for the boardwalk and the water, or across the Bridge Tunnel to Chincoteague for the ponies and the quiet. Make it the week, not the day trip.
The mountain week. Shenandoah with a cabin near Luray, Skyline Drive in sections, Luray Caverns for the rainy day, and Charlottesville with Monticello on the way home.
The long weekend from Washington. Mount Vernon, Old Town Alexandria and a Loudoun County winery with a lawn for the children. This is the trip for a family already in the capital.

Chincoteague at dusk. Ten dollars a car and the ponies on the marsh.
Regions at a Glance
The Historic Triangle and Richmond
Williamsburg, Jamestown, Yorktown and the capital. The founding era week, and the one most families should pick first.
Coastal Virginia and the Eastern Shore
Virginia Beach, Norfolk, the Bridge Tunnel and Chincoteague. The beach week, with ponies at the quiet end.
Shenandoah and Charlottesville
Skyline Drive, Luray, Monticello and the Blue Ridge. The mountain week, two hours from Washington.
Northern Virginia and Loudoun
Mount Vernon, Old Town Alexandria and fifty wineries within an hour of the capital. The long weekend, not the full trip.
Must see and do
Six things worth building a Virginia trip around, picked for families, with what they cost where a cost exists.
Photos via Unsplash.
Doing It With Children
Virginia works for children who are ready to be told a story. This is how to tell it.
Williamsburg needs a plan, not a wander. Pick the trade shops, the fife and drum, the courthouse trial, and the evening ghost walk for the older ones. A full day, with the ticket bought online, and lunch at the Cheese Shop.
Yorktown beats Jamestown under ten. The American Revolution Museum at Yorktown has a camp with cannons you can stand by and a farm. Jamestown Settlement has the ships. Both are better than the archaeological sites for small legs.
Hawksbill is the scramble. The high point of Shenandoah at 4,051 feet, a short steep trail from Skyline Drive and rocks at the top. Old Rag is an all day scramble for teenagers only.
The ponies are at dusk. Chincoteague ponies graze the marsh along Beach Road most evenings. The refuge is ten dollars a car, the beach beside it is wide and empty, and the Pony Swim in late July needs a year’s notice.
Luray Caverns is the rainy day. The biggest cave system in the east, a stalactite organ, and an hour underground at a steady 54 degrees. Twenty minutes from Skyline Drive.
Worth the Money in Virginia
Virginia is cheap. These are the four things worth paying for properly.
Monticello’s house tour. About 42 dollars an adult, a few dollars for children, and the only way inside Jefferson’s house. Book the first slot of the morning before the heat and the crowd.
A colonial tavern dinner in Williamsburg. The King’s Arms or Christiana Campbell’s, candlelight, peanut soup and a fiddler. Expensive for what it is and the evening the children describe.
A cabin on Skyline Drive. Skyland or Big Meadows lodges inside the park, or a cabin near Luray. Waking up above the valley with deer in the meadow is the mountain week done right.
A Chincoteague pony boat tour. A small boat around Assateague to see the ponies, the eagles and the lighthouse from the water. Cheaper than it sounds and the Eastern Shore afternoon.
Things That Surprise First Timers
Williamsburg is a real town. People live in it, the college is next door, and the interpreters do not break character. There is nowhere else in the country doing this at this scale.
Skyline Drive has a speed limit and it is enforced. 35 miles an hour for 105 miles. Plan a section, not the whole road.
The Bridge Tunnel goes underwater twice. And there is a rest stop on an island in the middle of the bay. Children want to stop.
Virginia Beach water is warm. Swimmable from June to September, warmer than anything north of the Carolinas, and the boardwalk is three miles of bikes and ice cream.
Interstate 95 will ruin a plan. Washington to Richmond is two hours on paper and four on a Friday. The train is the answer.
Where I Would Start
Five people, the last week of April, and the history week.
The train to Williamsburg, or the early drive. Amtrak from Washington beats Interstate 95. Three nights in Williamsburg with the ticket bought online and the Cheese Shop for lunch on day one.
Yorktown and Jamestown as days. The Revolution museum and the camp at Yorktown, the ships at Jamestown Settlement, both on the combination ticket. Back to Williamsburg for the ghost walk.
Richmond on the way north. The Civil War museum at Tredegar, the capitol, and a night in a real city before the mountains.
Two nights in Shenandoah, Monticello on the way home. Skyline Drive in a section, Hawksbill for the scramble, Luray Caverns if it rains, and Jefferson’s house on the last morning. The beach and the ponies are the second trip.
Virginia by the numbers
Facts to know before you go
Ways to travel
Virginia is not one kind of trip
How you move through it changes the trip more than which places you pick.
Road trips
Washington to Shenandoah is about two hours, to Williamsburg about three, to Virginia Beach about three and a half. All three make a real loop with a car.
For example: Washington to Williamsburg to Virginia Beach and back over a week.Walking and hiking
Colonial Williamsburg is entirely walkable once you park, and Shenandoah has trails from a half mile boardwalk to an all day Old Rag scramble.
For example: the Hawksbill summit trail off Skyline Drive with rocks at the top.Rail journeys
Amtrak’s Northeast Regional runs Washington to Richmond to Williamsburg, which beats Interstate 95 on a Friday every time.
For example: Washington to Williamsburg by train with the car left at home.Guided and small group travel
The Monticello house tour, a ranger walk in Shenandoah, and a pony boat around Assateague. The guided hours are where the founding era stops being a textbook.
For example: the first Monticello house tour of the morning.Explore by interest
What families come to Virginia for

History
150 years in one state
Colonial Williamsburg, Jamestown, Yorktown and Monticello cover more than 150 years of American history without leaving one state.

Nature
Skyline Drive and Old Rag
Shenandoah’s Skyline Drive, Old Rag Mountain and the Blue Ridge Parkway give families real elevation and real trails within a half day of Washington.

Beach
Boardwalk to the Eastern Shore
Virginia Beach’s boardwalk and the Bridge Tunnel out to the quieter Eastern Shore cover both a busy beach week and a slow one.

Food and drink
Crab, ham and wine country
Chesapeake blue crab and Virginia ham on the coast, Loudoun’s wineries and breweries inland, and Richmond’s growing restaurant scene.
Something unexpected
Only in Virginia

Only here
A town that stays in character
Colonial Williamsburg is a living history site, not a museum with actors. Interpreters stay in character, the trade shops make things, and the town itself is the exhibit.

Drive it
A bridge that goes underwater twice
The Chesapeake Bay Bridge Tunnel links Virginia Beach to the Eastern Shore over 17.6 miles, with a rest stop built on an artificial island in the middle of the bay.

Two houses
Two presidents an hour apart
Jefferson’s Monticello and Washington’s Mount Vernon both sell timed tickets and both are built for a real family visit, not a quick photo stop.

Late July
Ponies that swim a channel
Every year the Chincoteague ponies are herded across the channel from Assateague at the Pony Swim, a tradition since 1925 and the book Misty made famous.
Combine It With
The United States. The country guide this page sits under. Entry rules, driving, tipping and how the other states compare.
Washington, D.C. Two hours from Shenandoah and three from Williamsburg. Free museums, the Mall and Mount Vernon on the way south.
North Carolina. The Outer Banks are two hours south of Virginia Beach, and the Blue Ridge Parkway runs from Shenandoah down into the Smokies.

Plan Virginia with Nicole
Tell me who is coming, and when.
Virginia trips work best when you pick one region and build around it rather than trying to string Williamsburg, Shenandoah and Virginia Beach into a single week. I can help you decide which region fits your family and get the timed tickets booked before they sell out.
Nicole Damiano, ASTA Verified Travel Advisor · Certified Family Travel Advisor with FG Luxury Travel. Adventures We Seek is my travel blog and planning resource. Trips are booked through Favorite Grampy Travels.
Poppy marks the family parts. Wherever you see her, that section is written for traveling with children.
Virginia, Answered
The ones that come up in almost every planning call. If yours is not here, ask me.
How many days for Williamsburg?
Four. Two for Colonial Williamsburg itself, one split between Jamestown and Yorktown, and one for Busch Gardens or Water Country. Kids hit a history wall after two straight days, so put the theme park in the middle.
Is Colonial Williamsburg good for younger kids?
Yes, and better than most historic sites. Rent a costume at the visitor center, join the militia muster, watch the trades, and let them run the green. The daily kids’ programs are built for ages five to twelve. Teens do better with the evening ghost walks and the courthouse trial.
Shenandoah or the coast?
Shenandoah for short hikes, waterfalls, deer at the roadside and Luray Caverns, ninety minutes from Washington. The coast for Virginia Beach’s boardwalk, the aquarium and the Chincoteague ponies. Williamsburg sits between them, so a ten day loop does all three.
When do the Chincoteague ponies swim?
The last Wednesday in July, with the foal auction the next day. It is crowded and it is a real event. The ponies are there all year on Assateague and the boat tours from Chincoteague see them any month.
When should we go?
April, May, September and October for the best weather everywhere. Summer is hot and humid but the beach and the water park make it work. October on Skyline Drive for color is packed on weekends. December in Williamsburg for the Grand Illumination is a family tradition worth planning.
Keep exploring from Virginia
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