Our Trip to Williamsburg with Toddlers

Alex and I were blessed to get to spend a week in Williamsburg, Va with his family at the Greensprings Plantation Resort. Traveling with young kids is challenging. Why would you not want to pack up all of your kid gear and do pretty much everything you do at home in a new environment (that is almost never childproof).

Williamsburg would not be at the top of the list for places to go with a young family. But the beauty and peacefulness of the area was well worth the challenge. I love how all of the businesses have blended into the colonial style so places like McDonalds don’t steal your attention.

Our guys weren’t quite ready for a day at Busch Gardens or Water Country. Although, we considered going to Busch Gardens with a twilight ticket just to go to the Sesame Street themed area of the park. And Colonial Williamsburg is nice to walk through, but the tours are tricky because it’s difficult to get in and out of the buildings with a double stroller (even with a Kinderwagon).

sign from Williamsburg Coffee Shop

So what do you do if you are vacationing in Colonial Williamsburg with toddlers?

Plan to stay in a hotel or resort that has enough space where you have room to relax. We would have been miserable in a traditional hotel room. But our room at the resort had two bedrooms, two bathrooms, a living area, kitchenette, and dining area. Lots of room to visit and play!

Swim daily, sometimes twice. There was a great pool at our resort, and we enjoyed swimming with the boys. We were sure to take the proper swimming floats so that everyone could relax. Will did great with his puddle jumper. Luke and Cole were still too little for theirs, so they ended up trolling through the pool in spring floats. (which I loved because I could hold on to one and float/swim along with them)

We took the ferry near Jamestown across the Jamestown river and back. Will loved that because we got to drive our van on the boat. The only downside with riding the ferry was that we didn’t really have a plan of what we were going to do when we got to the other side. But it was a great time for Luke and Cole to take a nap!

Will looking out on the Ferry

We took a stroll down Duke of Gloucestershire and looked at the colonial style buildings. The horse drawn carriages were a huge hit with the kids! There is an old fashioned candy shop we visited twice for a special treat and one evening we stayed for an outdoor concert. I was able to sit with the kids for about 20 minutes of it before they needed to stroll again.

playing colonial games

Go to VA Beach for the day. Sunday afternoon, we loaded up for VA beach which was only a little over an hour away. We could not have chosen a better day or time. We got to the beach around 3:30 and parked near 6th street. The weather was perfect and the beach was surprisingly not crowded. The boys loved playing in the sand.

We had a great time visiting with our family. One particular highlight was running into a gentleman dressed like Donald Sutherland in Pride and Prejudice checking out at Martins grocery and then ran into him again in the parking lot driving off in his Prius blaring classical music. Only in Williamsburg!

This wouldn’t be a good vacation related post if I didn’t share more pictures so, enjoy the cuteness!

Will swinging with Alex’s parents


Alex and the twins

Candy Shoppe visit

A Happy Customer.

Boy Meets Fountain.

Taking it all in. (Do we need to address the ghosts of sunburns past on my back?)

Father, Son/Father, Sons

A memory to last forever.

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About Jamie

Jamie is a creative-techie mom, raising three boys under three (twins!) with her husband in Pennsylvania. Jamie now writes at The Red Robinson, www.theredrobinson.com


  1. Barb a.k.a. Memaw says:

    This was a great time for Memaw and Papaw, too! It was worth every minute of anticipation!

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