Virginia Road Trip Itinerary Ideas

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When I was 13 my parents decided they were going to pick everything up and move to Virginia. Most kids my age would have hated the idea of moving from the only place they really ever knew. But for me, it was a gateway out of a living nightmare as the “fat” girl. My life up until that point was full of bullying and sexual harassment, so the idea of saying goodbye to the dredges of teenage life in my hometown felt like a miracle to the 13-year-old me.

Long story short, things fell through, and I spent the majority of my teen years hiding away. A lot has happened since that summer, 20 years gives a lot of time for someone to change, recover and become something. I will not lie, I have always wondered what would have happened if my family had moved to Virginia. Would things have been better or worse? While there is no true way to know, however, looking back there are things I’m so grateful for today that might never have happened.

As the years past, Virginia was a place where my family would frequently visit for vacations and became like a second home for me. The majority of my life was revolved around historical reenacting so it shouldn’t come as a surprise that our vacations revolved around Williamsburg with Busch Gardens thrown into the mix. It was educational and fun, a good combination for families with kids. So when Peter and I both stated an interest doing a road trip through Virginia, I knew one thing was for sure, we needed to go beyond the Clydesdales and Governers Palace of my past family vacations. But the question was, what did we want to see?

We have different interests that collide into similar ones, so finding the happy medium usually comes along with a hodgepodge of attractions. Peter loves history and beaches, I love dark odd history locations and animals. Four things that can seem very difficult to find a happy medium for, but not entirely impossible.

Developing the road trip itinerary through Virginia was decided on our travel routes based on the availability, price, and timing of each attraction we were heavily interested in. So as you might have seen in our West Virginia road trip we developed a circular path to help optimize our route from home and back again.

Maybe someday we can pick up our lives and travel in a camper or van, but for now, short State specific, dedicated road trips are a great way to learn about the history of each United States during our available time off. So let’s get right into it, here are the locations we visited during our road trip through Virginia.

The Itinerary

We first started our road trip in Alexandria, Virginia, just outside of Washington, DC. With so many things to see in the capital, it is nice to break outside of the city and watch from afar all the hubbub that goes on.

Alexandria, Virginia

Hen Quarter

Hen Quarter is a great location for fried chicken and southern hospitality. Located on the corner of King St and S. Columbus St. this location was the perfect spot for a late afternoon lunch. The chicken was flavored to perfection and cooked without the extensive grease that is typical of many fried chicken options.

King Street Mile

The historic area of Alexandria, King Street Mile is decorated with local businesses and reminders of the history that helped build America. Just off the mile you can find the Stabler-Leadbeater Apothecary Shop and walk into the residential area that many call home just outside of Washington DC.

Mount Vernon

Home to George Washington, Mount Vernon is situated on the bank of the Potomac River overlooking Washington, DC. While Mount Vernon is technically not located within Alexandria itself, it’s proximately is close enough to include in the list of experiences of Alexandria.

Stabler-Leadbeater Apothecary Shop

Located just off of King Street Mile, this historical apothecary allows you to see where time stops. The shelves are lined with rows of medicine containers, general store products and house supplies that once were used by our ancestors. Here you can also see a letter signed by Martha Washington and learn about the different remedies thought to cure numerous ailments.

Sugar Shack Donuts

The only place that combines donuts and prohibition. Unlike the Sugar Shack Donuts, we found in Virginia Beach, the one in Alexandria offers up a little secret. Just on the inside of the doorway, there is a fack door that leads to a speakeasy called Captain Gregory’s.

During morning hours the doorway can be easily missed, something that was well needed during the prohibition era, but if you look for the single bell at the top corner of the wall, you will find the entrance to a slightly more adult desired restaurant.

Sugar Shack Donuts although not my favorite option, was one of Peter’s. This location, although unique, is part of a small chain of donut shops located throughout the Virginia area. So if you miss out on this one, don’t be surprised to find one just a few towns over.

Torpedo Factory Art Center

We love art. It is one of our favorite souvenirs when traveling. So any chance to find a location dominated by artist is a huge win. The Torpedo Factory Art Center is exactly that, a location for local artists to set up shop and provide the public with not only a great place to gather, but to teach as well.

Charlottesville, Virginia

Monticello

Home to Thomas Jefferson, Monticello is situated on the top of a small mountain (“little mountain” the meaning of Monticello in Italian) just outside of Charlottesville. The plantation provides you with a chance to learn about how Jefferson lived and died. You can also gain a better understanding on the life of Sally Hemings and the different positions within slavery.

University of Virginia

If you are a campus enthusiast, the University of Virginia should definitely be on your list of places to visit. Founded by Tomas Jefferson, you can see the similar architecture of Monticello and learn about the history of the University through a private guided tour.

Chincoteague, Virginia

Sandy Pony Donuts

By far one of the best donut shops we have visited to date. Located behind the H&H pharmacy, this food truck provides you with deliciously hot donuts made while you wait.

Ropewalk Restuarant

Located on the western side of the island, the Ropewalk Restuarant offers patrons the option to sit inside or outside while enjoying the seafood & drink options.

Assateague Island

With my love for horses and all things equine, Assateague Island offers numerous different activities to keep you busy. To enter the Island you can purchase a weekly pass starting at $20 per vehicle. There are free-fee days, so check the National Park Services website for an updated calendar of these days.

Lighthouse

A short walk from the lighthouse parking lot to the Assateague Island Lighthouse will require an exuberant amount of bug spray, but the view itself is worth it. As you walk through the swampy woods you have a chance to encounter numerous different wildlife. If you want to explore the lighthouse, check the times listed on the bulletin board before entering onto the trail.

Assateague Wildlife Loop Trail

The wildlife loop trail is over 3 miles long that allows you to encounter numerous different types of wildlife. For the majority of the day, visitors can walk, run, bike or rollerblade through the loop to enjoy the views and wildlife experiences. The paved trails allow for wheelchair access and after 3 PM cars are allowed on the loop as well.

Toms Cove Visitor Center

A great place for children to learn about the different animals they may encounter, the Toms Cove Visitor Center also has a great souvenir shop in which proceeds go towards the care of the island.

Assateague Beach

This is probably one of the best beaches we had a chance of exploring over the summer. The waves were extremely high, giving us a chance at boogie boarding with high expectations. One of the best parts of this beach is that you get to park right up against the beach unlike the numerous Jersey Shores we are used too. When you are ready to head home, you don’t have to sit in a wet swimsuit with sand crammed into numerous different crevices, instead just head to one of the changing rooms and showers to get a little more comfortable.

Chincoteague Carnival Grounds

Unfortunately, we did not get a chance to experience the Carnival Grounds, but after talking to locals we learned that throughout the summer the grounds are a great place for some family fun. The grounds are open during the week of July 4th and Pony Penning week. We hope to go back soon to gain a better insight into the experience that Portly Passengers would have during the Annual Chincoteague Volunteer Fireman’s Carnival.

Virginia Beach, Virginia

We opted to find a hotel just outside of the main strip of Virginia Beach. The hotel offered walking distance to a beach just one block away. The secluded location allowed us to leave for lunch and enjoy to relaxing waves of the Chesapeake. But this didn’t stop us from exploring the town after the sun went down.

Don’t feel left out in purchasing clothing while exploring the city, check out our list of plus size shops within Virginia Beach.

The Shack

An adult hang out (21 and over), filled with lawn games and a chance for extreme mingling. Located towards the end of the Atlantic Ave, the Shack is a great place to grab a drink and just hang out for the night talking to locals and visitors alike.

Froggie’s

Located just over the bridge on route 60, Froggie’s is a quint location for perfected BBQ. While this is about a 20 minute drive away from Atlantic Ave and the main strip of Virginia Beach, it’s well worth the drive.

Atlantic Ave

The main strip of beachfront hotels and restaurants, Atlantic Ave gives you a great beach town feel. While walking down the avenue you will find that the city provides entertainment for all visitors through the hiring of professional street performers. Don’t worry about paying the performers, the city does it themselves.

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The Portly Passengers provides plus size inclusive travel tips and advice for anyone who is looking to explore the world. From seat sizes on airplanes to exploring museums, restaurants, and nature Melissa & Peter have the experience and stories to help guide you through it.