Looking for a Virginia road trip itinerary? Here’s one created by a local!
Thinking about hitting the open road for an epic Virginia road trip? I’m a Northern Virginia native, and I’ve spent countless weekends exploring every corner of the state—from historic spots like Colonial Williamsburg to natural gems like Luray Caverns.
Virginia has so much to offer, it’s tough to keep this itinerary to just 7 days! Based on my own experience as a full-time traveler and photographer/videographer, I’ve written this guide to help you see the best of what the state has to offer.
Short on time?
Here are the best guided tours in VA for history, charm, and unforgettable stops:
And if you’re visiting from out of town, here are some great car rentals!
📍 Road Trip Day 1: Discover Alexandria and Mount Vernon
Morning
Start with a scenic drive to the charming, historic city of Alexandria. It’s one of the easiest Virginia day trips from Washington DC, just about 20 minutes away, depending on traffic. I recommend driving outside of rush hour (which can start as early as 7 AM), if you can.
Founded in 1749, and was once a bustling port town, Alexandria is now a cute cobblestoned town perfect for tourists (and photographers!). Stroll along King Street, the heart of Old Town Alexandria, which is full of boutiques, art galleries, and historic buildings. Don’t miss the Hollensbury Spite House, Alexandria’s tiniest mansion!
Check out the Torpedo Factory Art Center, a former munitions plant now featuring artists’ studios and galleries. For Brunch head to The Majestic. Their Brisket Omelette is incredible, and will definitely keep you full until dinnertime!
Afternoon
After brunch, make your way to Mount Vernon, the former residence of George Washington. Located just 20 minutes from downtown Alexandria, spend your afternoon exploring this beautifully preserved mansion on this informative guided tour (I’ve done it myself, and I highly recommend it!).
There will be plenty of photo opportunities during the tour, and you can also snap some photos along the Potomac River!
➡️ Click here for the best Mount Vernon + Alexandria Tour!
Evening
Return to Alexandria for dinner. Try out Virtue Feed + Grain, a popular local restaurant in a revamped 18th-century granary, offering elevated pub grub. Their steak and fries are delicious, juicy, and cooked to perfection!
Afterward, you can also explore Old Town Alexandria’s spookier side with a guided ghost tour and pub crawl.
➡️ Click here for a fun ghost tour and pub crawl in Alexandria!
Wrap up your evening with a leisurely stroll along the Alexandria waterfront, getting some shots of the beautiful sunset over the Potomac.
Where to Stay in Old Town Alexandria
- Hotel Heron Old Town Alexandria – Every major attraction is within walking distance from this cozy hotel. There are dining options nearby and onsite! Book your stay.
- The Alexandrian Old Town Alexandria, Autograph Collection – Located in a historic, waterfront district with Washington-era homes, King Street shopping & foodie restaurants close by. Book your stay.
📍 Road Trip Day 2: Northern Virginia Adventures (Old Town Fairfax, Annandale, Vienna)
Morning
Start your day in Old Town Fairfax. Just a 30-minute drive from Alexandria, Fairfax has a rich history dating back to the 1700s. Explore the Fairfax Museum and Visitor Center, and stop by the Fairfax Courthouse (where the infamous Depp vs. Heard case was held!).
Stroll along Main Street and check out De Clieu Coffee, known for its incredible brewed coffee and delicious pastries. If you’re looking for a hearty breakfast, try one of my favorite Irish pubs, The Auld Shebeen, for a delicious and hearty Irish breakfast!
Looking for more foodie adventures in Fairfax? I love the Market Eatery Food Hall in H Mart Korean Grocery. For the best Taiwanese bubble tea, go to YiFang Taiwan Fruit Tea in Fairfax. Their Mango Pomelo Sago, Mangocado, and Taro Latte (made with fresh taro) are my favorites!
Afternoon
Next, head over to Annandale, about a 15-minute drive from Fairfax. Known as “Koreatown,” Annandale offers some seriously authentic Korean cuisine. A must-visit is Kogiya Korean BBQ, where you can indulge in an all-you-can-eat meat feast.
I also recommend The Block Foodhall & Bar, which has a good variety of Asian food, including poke bowls and other street food. The Block is the perfect place to capture some drool-worthy photos! After your meal, take a walk at Mason District Park, which has plenty of beautiful wooded trails, perfect for an afternoon break.
Evening
Your final stop is the town of Vienna (my hometown!), just a 10-minute drive from Annandale. Vienna is known for its schools, parks, and community events. There are so many things to do in Vienna, it’s hard to name just a few!
I recommend spending some time at Meadowlark Botanical Gardens, a 95-acre garden with stunning landscapes and seasonal blooms. You can learn about the town of Vienna at the Freeman Store on historic Church Street, and stroll along on the historic W&OD trail, a former railroad line.
Here are some dinner recommendations in Vienna Virginia. I go to these places often, at least once a week!
- Hawk & Griffin – the best British pub in Vienna, their signature “Beef and Veg Pasties” are the best
- Caboose Tavern – amazing burgers, quality beers
- Bear Branch Tavern – great food and service overall, plus they open late!
- Nozzo Pazzo Delicatessen – a great spot for coffee and pastries, voted Northern Virginia’s Best Breakfasts in 2024. Try their cinnamon rolls and breakfast sandwiches, made on fresh croissants!
Where to Stay in Fairfax/Northern Virginia
- Hilton Garden Inn Fairfax – Good rooms, good service, and decent amenities. Budget-friendly too! Book your stay.
- The Ritz-Carlton, Tysons Corner – This upscale hotel is one of the most luxurious hotels in Northern Virginia. A stay here is a must if you’re looking for luxury in Northern Virginia! Book your stay.
📍 Road Trip Day 3: Middleburg and Shenandoah Adventures
Morning
Start with a scenic drive to Middleburg, about a 50-minute drive from Vienna, VA. Middleburg is a charming town with a rich equestrian history and picturesque landscapes. Begin your morning with a hearty breakfast at Common Grounds, a local favorite known for its cozy ambiance and delicious pastries.
Once you’re fueled up, explore the National Sporting Library & Museum for a glimpse into the world of equestrian sports and art. If you’re visiting on a Saturday, the Middleburg Farmers Market is always fun to stroll through.
Middleburg during Christmas Time is also a real treat. Their Middleburg Christmas Parade is fun for the whole family, featuring Santa Claus, vintage cars, and lots of corgis!
Afternoon
After a morning in Middleburg, head towards Luray Caverns, about an hour and a half drive from Middleburg. The drive itself offers breathtaking views of Virginia’s countryside.
Visit Luray Caverns, the largest cavern system in the eastern United States. You can also visit other caverns nearby like Shenandoah Caverns. I wrote an entire article comparing the two caverns (you should totally check it out!)
After, set your GPS for the Shenandoah National Park, one of the best attractions near Luray Caverns, via the Blue Ridge Parkway. You’ll drive a scenic route that offers stunning photo opportunities, quiet picnic spots, and numerous pull-offs to take in the scenery. I highly recommend visiting during the fall or spring seasons!
Tip: Consider taking this self-guided driving audio tour of Shenandoah National Park to explore the park at your own pace!
➡️ Click here for an informative Shenandoah National Park self-guided audio driving tour!
Evening
Continue your drive into Shenandoah National Park, a popular hiking spot. Skyline Drive is a fantastic route for an evening drive, with multiple overlooks to capture those Instagram-worthy shots.
For dinner, visit Big Meadows Lodge. The meals are hearty and rustic, making it the perfect spot to relax and unwind after a long day of exploring. Try their famous blackberry ice cream pie for dessert. It’s a local favorite!
You can settle into one of the park’s cozy lodgings or set up camp at one of the designated camping areas at Shenandoah National Park.
Where to Stay in Shenandoah National Park
(if you’re not camping it out)
- Graves Mountain Farm & Lodges – Woodsy lodge with amazing views, a great cabin feel while still feeling like you’re in a hotel. It’s also one of the few hotels in the area with air conditioning! Book your stay.
- Cave Hill Farm Bed & Breakfast– This B&B is 50 minutes away from Shenandoah National Park. If you’re looking for a peaceful and charming stay with a delicious breakfast, this is it. Book your stay.
📍 Road Trip Day 4: History and Heritage in Charlottesville
Morning
Start your day early to make the most of it. The scenic drive from Shenandoah to Charlottesville is roughly 70 miles and should take about 1.5 hours. You can drive along the Blue Ridge Parkway or the faster US-33 route, both offering picturesque views.
Once you arrive in Charlottesville, head straight to the Downtown Mall, one of the longest pedestrian malls in the country. Here, you’ll find a mix of unique shops, art galleries, and street performances.
Grab a coffee at Mudhouse Coffee Roasters, and keep exploring Charlottesville!
Afternoon
Visit Monticello, the historic home of Thomas Jefferson. Located just a few miles from downtown, this UNESCO World Heritage site offers guided tours that explain Jefferson’s life and legacy.
Pro tip: Book your tickets in advance to skip the lines, and wear comfortable shoes as there’s quite a bit of walking involved.
For lunch, head to Bodo’s Bagels—a local favorite known for its fresh, New York-style bagels and delicious sandwiches. For something more hearty, The Whiskey Jar offers hearty Southern fare and a great selection of craft beers.
After lunch, consider a visit to the University of Virginia campus, another UNESCO World Heritage site designed by Jefferson himself. Stroll through the iconic Rotunda and the Lawn, and if you want the full guide of these historic sites, consider taking a guided tour!
Evening in Charlottesville
Wrap up your day with dinner at The Local, a unique farm-to-table restaurant that showcases the region’s best produce. For dessert, splurge on some mouthwatering gelato at Splendora’s Gelato Café back on the Downtown Mall.
Where to Stay in Charlottesville
- Oakhurst Inn Charlottesville – Pet-friendly boutique hotel near the University of Virginia, nestled in a quiet area not too far from the city’s major attractions. Book your stay.
- Keswick Hall – A truly beautiful property, featured in the Best Golf Resorts in the Mid-Atlantic. Nestled in the serene Blue Ridge Mountains, this luxurious retreat offers everything you need for a perfect getaway. Book your stay.
📍 Road Trip Day 5: Richmond’s Urban Charm
Morning
Drive from Charlottesville to Richmond, Virginia’s capital. Once you arrive, visit the Virginia State Capitol. Designed by Thomas Jefferson, this iconic building is a must-see. Consider taking a guided tour to learn about its rich history and significance.
➡️ Click here for an educational walking tour in Downtown Richmond!
You can also explore the Virginia Museum of Fine Arts (VMFA): Home to an impressive collection of art from around the world, the VMFA has lots of unique exhibits including Fabergé eggs and a stunning sculpture garden.
Afternoon
Stroll along the Canal Walk for a scenic view of the James River, and read up on Richmond’s history with the historical markers to guide your way.
Stop by Carytown, a small district offering a variety of unique shops, boutiques, and eateries. You can also take this Carytown food tour, where you’ll sample delicious food at five to six different tasting spots!
➡️ Click here for a fun food tour in Carytown!
Evening
For dinner, head to Mama J’s Kitchen for some of the best Southern comfort food in the city. The Veil Brewing Co. is also a local favorite, offering a great selection of unique brews.
Where to Stay in Richmond
- The Berkeley Hotel – A charming boutique hotel nestled in a hip district with a varied dining scene, plus a riverside walkway at Pipeline Overlook. Book your stay.
- The Jefferson Hotel – A gorgeous five-star hotel that originally opened in 1895. The hotel is a 7-minute walk from Monroe Park and 1 mile from the James River. Book your stay.
📍 Road Trip Day 6: Step Back in Time on Colonial Parkway
Morning
Begin your day with a hearty breakfast at Millie’s Diner in Richmond, known for its eclectic menu and cozy atmosphere. Once fueled up, hit the road and head east towards Jamestown, about an hour’s drive from Richmond.
Take the picturesque Colonial Parkway to Jamestown. This 23-mile scenic route connects the Historic Triangle of Jamestown, Williamsburg, and Yorktown, offering stunning views of the James River and lush landscapes.
In Jamestown, you can visit the Jamestown Settlement, a re-creation of the first permanent English settlement in North America.
Afternoon
Drive back on the Colonial Parkway to Williamsburg, where you can walk through restored 18th-century buildings, watch blacksmiths at work, and engage with actors who bring America’s colonial past to life. For a more educational experience, consider taking this guided tour of Colonial Williamsburg.
➡️ Click here for a fun yet informative Colonial Williamsburg tour!
But if that’s not your cup of tea, you may consider these other things to do in Williamsburg.
For lunch, I highly recommend The Cheese Shop. Their famous “House Dressing” makes their sandwiches absolutely incredible.
Evening
For dinner, try the King’s Arms Tavern. They serve colonial-era fare in a unique, historic atmosphere. After dinner, explore a different side of Colonial Williamsburg with a fun (and spooky) Colonial Williamsburg ghost tour!
➡️ Click here for the best a Colonial Williamsburg ghost tour!
Where to Stay in Williamsburg
- Holiday Inn Express Williamsburg Busch Gardens Area, an IHG Hotel – This is about 2 miles from Colonial Williamsburg and is in a nice, quiet area surrounded by trees. Aside from free parking and breakfast, kids also stay for free! Book your stay.
- The Williamsburg Inn – This is the only Forbes Travel Guide Four-Star rated resort in the Historic Triangle. It has seen many famous visitors and is still beautifully maintained and oozes luxury! Book your stay.
📍 Road Trip Day 7: Sun, Sand, and History in Norfolk and Virginia Beach
Morning
Drive from Williamsburg to Norfolk. The drive should take around 1 hour, depending on traffic. Once in Norfolk visit the USS Wisconsin, a retired battleship docked at Nauticus, a maritime-themed science center and museum.
Afternoon
Explore Norfolk’s Neon District, a hub for street art, galleries, and trendy eateries. Snap some photos of the murals and grab a bite at one of the local cafes.
For lunch, I highly recommend Freemason Abbey – a 19th-century church turned restaurant known for its seafood. Try their famous she-crab soup!
Evening
After exploring Norfolk, head over to Virginia Beach for some sun and sand. Relax on the beach and explore First Landing State Park, a park that marks the site of the first landing of the settlers who founded Jamestown. You can also kayak and see dolphins on this tour.
➡️ See dolphins in this fun sunset kayak tour!
For dinner, stop by Repeal Bourbon & Burgers. This speakeasy-themed restaurant serves hearty, unique hamburgers & specialty cocktails. One of the best burgers I’ve had (and the best bacon-brussel sprout side!)
Road Trip Map
How to Get Around Virginia
Virginia was made for road trips. The best way to get around is by car, whether it’s your own or a rental. Having your own ride means you can take your time, follow scenic backroads, and stop to explore small towns whenever something catches your eye. I highly recommend this car rental!
➡️ Click here to book your car rental!
Is it Safe?
Virginia is a very safe place to travel, with friendly communities, well-patrolled cities, and welcoming small towns. Most visitors explore comfortably without issues. When driving through rural or mountain areas, stay alert for winding roads, wildlife, and changing weather.
FAQs
Here are answers to some of the most frequently asked questions from fellow explorers who want to plan an epic Virginia road trip.
Is there anything interesting to do in Virginia?
Absolutely! Virginia is full of interesting things to do, from snapping photos of the scenic Blue Ridge Mountains to visiting historic sites like Colonial Williamsburg. Whether you’re into outdoor adventures or historic tours, there’s something for everyone.
What is the prettiest place in Virginia?
I think the prettiest place in Virginia is Shenandoah National Park, with its breathtaking Blue Ridge Mountain views, especially during the fall season.
What is the best time to visit Virginia?
The best time to visit Virginia is during the spring (April to June) or fall (September to November) when the weather is pleasant.
Final Thoughts
These are just a few highlights that make Virginia worth visiting – the state is brimming with history, culture, and natural beauty. Other good stops include Roanxoke, where you can hike up Mill Mountain and enjoy panoramic views of the city.
There’s also Chincoteague Island, famous for its wild ponies and serene beaches that make fantastic photo opportunities.
All in all, Virginia is a beautiful state to visit. It’s the perfect road trip destination that’s sure to help you create lasting memories.
Happy travels!
About the Author
Sasha is the founder of Little Happy Travels, a blog with tips and inspiration for combining work + travel and living the digital nomad lifestyle. As a business coach and remote worker, she’s spent the last few years traveling the world while helping others do the same. Follow for guides, tips, and personal stories on working from anywhere!
