Our Kid-Friendly Trip to Williamsburg

In September, I took Amalia to Williamsburg, VA, for a four-day, three-night, mommy-and-me trip. It was a time that we’ll never forget and kicked off a tradition of the two of us traveling together. She was the greatest little travel buddy, although she definitely kept me on my toes. 🙂 We packed our days with family-friendly meals and activities. I can’t recommend a trip like this enough.

Our itinerary was fun for both a 4-year-old girl and her 30-something mama. It’s been over two months since the trip and Amalia still talks about it regularly!


We flew into Richmond, VA, and rented a car at the airport. It was a quick and easy process, and they were able to provide a car seat.

After a 45-minute drive to Williamsburg, we settled in at Kingsmill Resort & Spa where we got an amazing condo with a waterfront view. It was great because when Amalia went to bed at night, I could sit in the separate living room and work or watch TV.

Kinsgmill Resort Williamsburg

The condo also had a kitchen, so we were able to make breakfast, and there was and a washer/dryer which was clutch. It was about 10 minutes from downtown, and a stone’s throw from Busch Gardens, so we didn’t have to drive far for any of our adventures.

That night, we headed into Merchants Square, a charming little downtown shopping and dining area that’s blocked off to traffic for a quaint and small-town feel. Amalia loved being able to run around without worrying about cars. It’s the little things with kids!

Before dinner, we did some shopping at The Carousel, the most adorable children’s boutique I think I’ve ever seen. Amalia picked out a dress and I bought the kids their Thanksgiving outfits. Then we popped into Perfectly Natural Soap because Amalia is obsessed with bath bombs and I promised her we would buy one if we saw it.

For dinner, we walked around the corner to La Piazza where they served fresh pasta and other northern Italian dishes. Amalia ate an entire appetizer portion of meatballs!


On Friday morning we woke up early and had toast in our room while Amalia played with her toys. I knew this was going to be a busy and exciting day so I wanted to make sure she had time to acclimate to where we were.

After breakfast, we went to the Bounce House Family Entertainment Center and had a blast. She was able to get her zoomies out and just be a kid which I think is so important when you travel with little ones. They need to have free time to do what they love so they’re in a better mood for everything else.

She jumped, she slid, we played hide and seek and had a great time. Everyone was masked and it felt very safe. We could have stayed all day but we got hungry for lunch.

I had asked for lunch recs on Instagram and had so many people tell me to check out The Cheese Shop in Merchant’s Square for sandwiches. It did not disappoint. Their house dressing is a thing of beauty, tangy and creamy and the perfect addition to any sandwich. I went back the next day and bought a jar to take home.

After lunch, we had rest time, another important piece of the puzzle when traveling with kids. Amalia needs her downtime (and so do I, TBH) so I let her watch a little iPad while I answered emails.

That afternoon, we headed to Busch Gardens for a few hours of rides, games, and treats. It was so much fun! I’ve truly never seen such a beautiful amusement park. It is divided into sections themed as different countries with a few little kid sections throughout.

We spent the majority of our time there at the Land of Dragons, a play area for small children that also has kid-friendly rides. The park wasn’t very crowded so she rode three rides in that section multiple times!

She also enjoyed the Sesame Street Forest of Fun where she got to meet Elmo (although she was too shy to take a picture with him) and go on a few rides as well.

My biggest tip for Busch Gardens with small kids is to rent a stroller at the entrance. The park is huge and involves lots of walking. It was totally fine for me, but she wouldn’t have made it without the stroller.

That night, we were scheduled to have a dinner at Food for Thought which I was super excited about, but Amalia was basically a zombie and I knew that was out of the question. I ordered her a pizza and she was asleep by 6:30 pm. It was a big day for a little gal!


We drove back to Merchants Square for breakfast at Illy Caffe where we were able to sit at an outside table and people watch. Again, Amalia was very into the closed-off street and did a little ballet recital for everyone else drinking their coffee. It was very cute.

We perused the Farmers Market and then did a little more shopping before heading to Colonial Williamsburg.

I let Amalia pick the first store and, shocker, it was Wythe Candy Shop. Her second choice was The Christmas Shop, where she insisted on buying a Christmas ornament for everyone in the family.

We hit up The Shoe Attic, which I had been told was right up my alley, and it was true! They had a ton of super cool shoes but also accessories, jewelry, and clothing. I bought a block print dress (of course) and Amalia loved looking around at the colorful clothes.

Next, we visited Brick & Vine to peruse home goods, furniture, and books. It was a gorgeous shop filled with blue and white decor. I could have taken half the store home with me.

For our last stop on the shopping tour, we picked out a little pewter chicken for Anel at Danforth Pewter.

We walked down the street to the historic area of Colonial Williamsburg, which is right next to Merchants Square. It’s a mile-long closed-off road filled with beautiful colonial homes, people dressed up in colonial clothing, shops, and horse and carriage rides.

Again, I’d recommend a stroller or wagon for this if you have small kids. It was fun to walk and go into some of the shops and sites. The most kid-friendly shop was the William Pitt store, which carried a good selection of kid-friendly souvenirs, gifts, and books. There are also costumes available for rent!

We popped into the Art Museums of Colonial Williamsburg and ate lunch in their gloriously spacious and air-conditioned cafe.

After lunch, we headed home for rest time again. We went to the River Pool at our resort and had a great time! You can float along a lazy river in tubes which was exactly what we needed after a busy two days.

We walked from the pool to the marina at Kingsmill for some kayaking on the James River. The water was as still as glass, and it was so quiet and peaceful. This was one of my favorite moments of the whole trip, just being out on the water with my girl.

That night, we were lucky enough to visit the Williamsburg Winery and eat at the Gabriel Archer Tavern on property. It was a beautiful night and it felt special to be on a vineyard. It’s been a while!

Thank you to Visit Williamsburg for sponsoring this post. All opinions, as always, are 100% my own.

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