Planning a Virginia road trip? If you’re looking for a family-friendly Virginia road trip itinerary filled with important American historical places, this seven-day route is a great place to start. From Colonial Williamsburg and Historic Jamestowne to Yorktown, Monticello, Appomattox, and Charlottesville, Virginia is packed with historic sites, museums, and places that bring U.S. history to life.
With so many historical things to do in Virginia, planning the best route can feel overwhelming. This seven-day Virginia road trip is designed to help you organize your time, reduce driving and stress, and visit some of the best historical places to visit in Virginia.
If you’re planning a Virginia history road trip, here’s the itinerary I would use to explore the Historic Triangle of Virginia and beyond.
Links, info, hotels links check and updated Sept 2026
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Jump to Specific Virginia Road Trip Days
The Seven Day Virginia Road Trip Overview
Depending on your starting location, this Virginia road trip itinerary could be done either direction. Most of these Virginia road trip sights are located in the Historic Triangle in Virginia. Look at a map to fully understand why it’s called “Historic Triangle”; Jamestown, Williamsburg, and York town are all very close together.
If you are driving south out of the area to go back home, consider moving the Norfolk adventure day to the last day for a quick wiggle stop on your way home. Most of the days in this Virginia vacation itinerary are not in any particular order; I switched up our tour of Virginia accounting for kid attention spans, topic of interest, and time needed.
The only historic Virginia site on this historical road trip list that is further away is Appomattox Courthouse. It is a two-and-a-half hour drive from Williamsburg to Appomattox, so plan to see Appomattox on the way in or out of the area.
If you only have time for a Virginia weekend trip, I would suggest Historic Jamestowne and Williamsburg. These were the most impactful during our road trip in Virginia, and these are true Virginia historic tours.
READ NEXT ~~~> If you have another week in your family road trip traveling Virginia, head north just a short distance to add Mount Vernon and Washington DC to your history lesson. Plan your DC trip with my post “Practical Tips to Make your DC Trip Easier” and add these “10 DC Hidden Gems Your Kids Will Love.”
Where Should I Stay During My Virginia Road Trip?
During this Virginia road trip, simplify driving by stay in one hotel during your one week vacation in the Historic Triangle area of Virginia. Make day trips, and sleep in the same place. As the main sites of Jamestown and Williamsburg are only 15 minutes from each other, the longest day-trip from Williamsburg is only one hour away in Norfolk.
For our Virginia travel itinerary, we chose to stay at the Historic Powhatan Williamsburg with Hilton Vacation Club only fifteen minutes away from Jamestown Settlement and five minutes from Williamsburg. Our family of six stayed perfectly in a two bedroom suite which felt more like our own personal apartment complete with a full kitchen and washer and dryer.
Historic Powhatan is a huge resort with full amenities including miles of walking trails, indoor and outdoor pools, multiple playgrounds, and even tennis courts. With options ranging from one room hotels to up to four bedroom suites, this is a perfect place also for an extended family gathering. Make sure you plan some downtime during vacation to enjoy hanging out as a family.
Day 1 – Appomattox Battlefield and Museum
Let’s head out on day one of this Virginia itinerary for seven days. Appomattox is a great day trip if you’re driving in from several hours or spent all day yesterday on your drive to Virginia. Appomattox Battlefield is only about an hour from our first overnight stop in Charlottesville, Virginia.
Visit Appomattox Court House National Historical Park
With the pivotal final battle and signing of the surrender document between Generals Grant and Lee, the small town of Appomattox, Virginia played an important role in the Civil War. Unlike other battlefield visits, Appomattox Court House has a small town to wander including the home where the surrender was signed, the jail, a store, and several buildings including a small museum.
Plan to spend a couple of hours here at least. Wander around by foot. Take a driving tour. Join a guided tour. Complete the Junior Ranger book. And if you homeschool with Classical Conversations like us, time to sing your history song… “Surrendered to General Ulysses S. Grant at Appomattox Court House in Virginia.”
Help your kids get even more interested in visiting this site, with an excellent kid’s picture book The Silent Witness about a doll that watched the surrender happen. When you’re in the house, you will see the room mentioned and the couch where the doll would have sat. History comes to life on this trip to Virginia! (And we just started 🙂 )
Visit the American Civil War Museum at Appomattox, Virginia
The American Civil War Museum at Appomattox is a five minute ride from the Appomattox Court House National Historical Park. Do the free national park, and follow it up with the high-quality paid museum to complete the rest of the story. Here you will see more than 400 artifacts from the battle including Robert E. Lee’s uniform and sword.
If you plan to visit here, consider purchasing the combo ticket which also gets you into the White House of the Confederacy in Richmond.
Take a Quick Trip to Richmond, Virginia
When traveling Virginia, it’s only a two hour drive from Appomattox to the next stop in Monticello. Leave time for an extra stop as you will drive right through Richmond, the capital of Virginia. Start learning about Thomas Jefferson driving past the Virginia Capitol in Richmond and its importance as the start of the neo-classical design in the United States.
Day one was only a short drive of less than an hour and a half from Appomattox to Charlottesville. This would be a great time to wander around the campus of the University of Virginia if you get there earlier in the evening, or you can just take in the town of Charlottesville. Spend the night in a Charlottesville hotel, ready to learn all about Jefferson and Monticello tomorrow.
Day 2 – Visiting Jefferson’s UVA and Monticello
Grab Breakfast at Bodo’s Bagels; Charlottesville, Virginia
For a true university experience while traveling Virginia, eat like a college kid at Bodo’s Bagels, a Charlottesville speciality. Before heading to the University of Virginia, walk right across the street for a delicious bagel breakfast sandwich from Bodo’s. It’s worth waiting in line. Once you have your food, head across to the university for a breakfast picnic.
Visit the University of Virginia
If you’re learning about Thomas Jefferson, you need to learn about one of his biggest accomplishments at the University of Virginia. Don’t just choose see Monticello.
Did you know that, when composing the words for his future tombstone, Jefferson considered founding this university as priority over his presidency? UVA a beautiful campus. Check out this self-guided walking tour to bring to life the campus of the University of Virginia. Make sure you learn about where Edgar Allen Poe stayed while he was a student there.
Visit Jefferson’s Monticello
A day at Monticello is the highlight of your visit to Thomas Jefferson’s hometown of Charlottesville. I can honestly say it’s my favorite historic house that we have visited.
- Watch a video about his life
- Explore the vegetable garden.
- Visit Jefferson’s beloved home and grave
- Learn about the construction of the house
- See Lewis and Clark artifacts inside the home
- Explore the gardens and lawn that he designed
- Read about his life and accomplishments at the museum
- Take a tour of the slave quarters and learn about the life
READ NEXT: Head to my in-depth post all about Monticello sights, tips, and history at “Monticello: How to Plan your Best Family Trip.”
Day 3 – Historic Jamestowne and Williamsburg
Day 3 is a busy day on this Virginia travel itinerary, but before planning this portion of your Virginia trip, you need to understand the difference between these places.
Historic Jamestowne vs Jamestown Settlement
Jamestown Settlement is a reconstruction of the fort. The outdoor living museum has colonial interpreters demonstrate for you their trades while the Powhatan characters show you their village, canoes, and lifestyle. Also outside are the three rebuilt Jamestowne ships, and you are able to climb aboard the Susan Constant. Not to be overlooked is the state of the art Jamestown museum inside which also has two movies to view.
In contrast, Historic Jamestowne is a national park site on the ruins of the original landing site where you can see current day archeology digs, see the original layout of the wall, experience the proximity to the water, and see original artifacts in the museum. Very different experience. Both great.
These are two different places. It is my suggestion that you visit them on two different days because it’s just a lot. Although you can visit them in either order, I think if you visit the original site first, the kids (and parents) would have more interest in all the reading at the museum.
Visit Historic Jamestowne, Virginia
Historic Jamestowne is a National Park site and includes the current and past archeological digs at the site. Started in 1994, archeological digs have been undertaken to discover the original site of the fort along the James River. This is such a different experience from the reconstructed fort. We loved it – especially my history-loving, archeology-loving kid.
- Drive the around the island, get out and explore, and see the land of the settlers
- Join a tour with a guide or archeologist and visit the current dig
- Walk along the water and take a nature walk
- See the infamous basement and church
- See artifacts at the Archearium
- Visit the glass blowing house and learn why Jamestown was a perfect location for glass production
READ NEXT More about Historic Jamestown on my detailed post “Historic Jamestowne: How to Plan Your Day.“
Wander the College of William and Mary
Let’s head to the College of William and Mary to visit the second oldest higher-learning institute. It was here that many founding fathers were educated including Thomas Jefferson. Let the kids wander and consider taking the self-guided tour around William and Mary. It’s a beautiful area.
It is on the opposite side of Williamsburg from the Visitor Center, so find a paid parking spot. You are going to stay in this spot for the rest of the night, so make sure it allows several hours.
Explore Colonial Williamsburg in Virginia for Free
Here’s the thing about Williamsburg, it is huge and more than you can do in a day. Wander the streets, get a feel for the layout of the town, admire the houses from the outside. You could even hire a buggy to take you around. There are places you can only get in with a ticket – we will do that another day – so prepare the kids that they won’t be able to perhaps do what other people are doing.
The modern-day town of Williamsburg is right there at the Colonial Williamsburg. You will see the houses, restaurants, and shops for “regular people” only blocks from the historic portion. Without rushing around to get the most from your one-day ticket to Williamsburg, you now have time to wander the historic town at your speed. For fun! You will have time to experience Williamsburg with kids on your ticketed day.
READ MORE ~~~> Be even more prepared for your Williamsburg day at “Colonial Williamsburg: How to Plan the Best Family Visit.“
Day 4 – Jamestown, Donuts, and Play Time
Visit the Jamestown Settlement
Take a day for a family visit to the Jamestown Settlement for a top-notch museum with some great outdoor exhibits. This is a great way to bring to life the Jamestown that you saw in ruins two days ago. Although you could spend all day here, I would plan to focus on the video inside and the outdoor exhibits. It completely depends on your kids interest and patience levels. Entrance here will be with your combined Jamestown-Yorktown ticket you purchased online.
- Wander the reconstructed settlement.
- See the reconstructed Powhatan village.
- Explore the replicas of the three original ships.
- Talk with the townspeople to see how they lived.
- Watch them cook, blacksmith, carve a canoe, build shelters, etc.
READ NEXT~~~> For detailed information about what to expect, read “A Family Visit to the Jamestown Settlement.“
Take a Snack Break with Duck Donuts
Although this is a national donut chain, it was our first experience, and it may be your first time at Duck Donuts too. It won’t be your last. Prepare to watch them fry your donuts as your pick your glaze and toppings for your specialized treat. The Duck Donuts in Williamsburg was way too close to my family’s condo during vacation to just go one time.
Visit Freedom Park and Botanical Gardens
Remember to take some time and let the kids be kids. Freedom Park in Williamsburg, Virginia has playgrounds and two miles of trails, but it has lots more to offer including history and a sense of adventure. This park is also the site of an 18th century cemetery, a Revolutionary War Battle, and one of the US’ earliest Free Black Settlements. Take a break from playing on the playground to walk over and check out the three historically recreated cabins.
The Williamsburg Botanical Garden in Freedom Park is member-maintained and a lovely little stroll. With more than 800 species of plants and trees, there’s shade here for a hot afternoon and little garden treasures for the kids to discover.
If you’re really pushing for a fun time, check out the GoApe Treetop Adventure Course. I wasn’t fun enough to splurge for this treetop ropes course, and if you aren’t either, make sure you let the kids know that it will not be part of their free playground fun.
Day 5 – A Day Road Trip from the Historic Triangle to Norfolk, VA
Let’s have a day of learning that doesn’t involve even more American history. The kids’ brains can only take in so much, and as my own kids like to remind me, all these places start to blend together after a while. And we will drive across Chesapeake Bay – it’s a good idea to let the kids see how big this thing is! Look at it on the map and see how it leads to Jamestown.
Visit the Chrysler Museum of Art
Plan to spend a couple of hours wandering the Chrysler Museum of Art – free art museum! Let your kids meet Pollock, Lichtenstein, and Warhol in person. This is a beautiful museum inside and out.
Wander Along the Norfolk, Virginia Waterfront
Plan to park and stay for several hours. There are even several nice restaurants along the water if you want to stay for a nice supper. How much time and money you want to spend can be variable. The garden is free, and you can see the battleship without difficulty without paying for the entrance. If you have more time, pay to go inside the amazing ship or the museum.
- Battleship Wisconsin and the Hampton Roads Naval Museum
- Pagoda and Oriental Garden – Free for a quick wander through a beautiful garden setting
- Armed Forces Memorial and Lone Sailor Statue
- Naval Station Norfolk – See the giant battleships and carriers that are being repaired at the Naval Station right across the water.
- Admire all the yachts and big boats parking here!
Learn at the MacArthur Memorial
Take the time to do some other US history learning at the MacArthur Memorial. Free admission to explore the life of General of the Army Douglas MacArthur and those who served with him during World War 1, World War 2, and the Korean War. We didn’t have time to do this!
Day 6 – Colonial Williamsburg
Since visiting Colonial Williamsburg is at the top of your must-see list, you may not want to save it until the end of your Virginia trip just in case you have to cut your trip short. However, I also think it gives everyone something to look forward to after exploring it for free on other days.
Visiting Colonial Williamsburg felt (to me) a bit like Disney World. You have an app that tells you what time and where the special programs are happening. You have to coordinate all that with the map to see where you can actually reasonably get. And you know that you will never be able to see it all at once. That’s why I suggest saving free places for wandering at other times.
Although you can get the three day Williamsburg ticket, there won’t be time during your one week vacation to return multiple times most likely. However, if you want to see every bit of it, there’s plenty to see.
Put on good shoes. Plan to eat lunch at a historic tavern. Bring some water and snacks. And prepare to be immersed in history.
READ NEXT ~~~>For detailed planning for your Williamsburg, Virginia itinerary, check out my guide “Colonial Williamsburg: How to Plan the Best Family Visit”.
Day 7 – Yorktown Museum and Battlefield
Visit the American Revolution Museum at Yorktown
The American Revolution Museum at Yorktown is the other part of the combination ticket you already bought for Jamestown. As they are made by the same people, they are very similar and equally amazing, state-of-the-art history museums. Williamsburg and Monticello were about Jefferson; this is about Washington and Hamilton.
- Watch some videos
- Explore exhibits in the museum.
- Head outside for a possible artillery demonstration.
- Explore the tent camp as would have been used by Washington.
- See the farm, house, and tobacco shed.
Visit Yorktown Battlefield
Yorktown Battlefield is an important part of history, but I will add, battlefields are pretty boring for kids visit. Yes, General Cornwallis surrendered to General George Washington ending the Revolutionary War. However, we’ve visited several battlefields, and most look like fields with lots of driving. We didn’t spend a lot of time here. Consider getting a Yorktown audio tour; I wish we had.
If your history buffs are up for it, download the NPS app, read everything at the Yorktown Visitor Center, complete the Junior Ranger badge, and soak it all up. If you just want to make the kids remember something, sing the Hamilton song about “Battle of Yorktown” and rap. Then drive over to see the still-in-place redoubts built by Alexander Hamilton and Lafayette.
It’s so cool to make history come alive. You can still see the wooden spikes sticking out of the mounds. They’ll remember this for sure.
Wander Around Yorktown, Virginia
Reward the kids for the battlefield listening for with Yorktown Harbor. Now, the kids can walk around town and get off museum energy. Park at the part of the Yorktown Battlefield close to the historic town, get out, and wander. Pull up the walkable Yorktown self-guided tour and wander around looking at the historic houses and streets. Award a prize to the first kid to find the cannonball stuck in the side of the house! Talk about bringing history to life.
The modern portion of Yorktown in a tiny town right on the water. There’s a small beach which is great for letting the kids splash in the water and play in the sand. Additionally, it is right on the river, so you will see some historic ships sailing by on cruises. Eat a meal in Yorktown, visit a few small shops, and have an ice cream.
~~~> Whew! That was quite the seven days you spend exploring Jamestown, Jamestowne, Williamsburg, Monticello, and so much more during this first of many trips to Virginia. If you are still not done exploring Virginia and are headed over to Washington DC, make sure you check out my post “6 Practical Tips to Make Your D.C. Trip Easier.”
~~~> Double Whew! If you’re wishing you had saved that link for our Virginia vacation rental, check out this link through booking.com to The Historic Powhatan in Williamsburg. It truly was the perfect location, plenty of space, and lots of great family-friendly vacation amenities.
My Favorite Travel Resources
- Booking.com – This is my go-to website for hotels, apartments, and even vacation home rentals to easily find places for my group of 6.
- Trip Advisor – This travel planning and booking website has been my go-to for decades. I especially use it to find nearby restaurants and activities.
- Viator – My go-to to find for city tours and experiences.
- Omio app and website – European train travel is easy for booking and keeping all tickets organized
- Radical Storage – Busy travel days sometimes means needing to leave your suitcase somewhere trustworthy. This worldwide option makes it easy.
- Welcome Pickups – I just found this company, but I plan to use them next time we need an airport or port transfer!
Thanks for stopping by my little corner! Here’s to your next adventure.
I’m Bobbie. After years of planning detailed family trips, I’m diving into travel advising. I’d love to take away the stress and plan a trip for you. Let’s get started today – click here to start.
You can count on me to share honest reviews and answer the questions you need to plan your own trip. My family of six is on a mission to discover all of Georgia’s amazing places, experience amazing road trips across the United States, and create a homeschool life along the way. We even world travel when we can!
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