Will's First Road Trip!

We took our first trip as a family of four to Williamsburg over the Memorial Day Weekend. It was a lot of fun and wasn't too expensive, thanks to a deal I saw on LivingSocial. With little ones, we got a 1-bedroom condo - with a full kitchen and washer/dryer. It was much better than a standard hotel room. Williamsburg is a great destination for us because it's only a few hours away and with just enough to do. As the kids get older, we will hit up the theme parks, but we stuck with the freebies this time.

Here is a summary of what we did -

Day 1: We got stuck in traffic on the way down so by the time we got there, it was 1pm. We ate at a buffet and then went to Walmart for some essentials. Will went to sleep super early that night since he hardly napped.

Day 2: Breakfast at iHOP. Then we drove the Colonial Parkway toward Yorktown (Beach). Anna wasn't feeling up for playing in the water, but she spent time finding seashells. After we got enough sun, we stopped by Ben & Jerry's before heading home for a loooong nap. That night, we went to Colonial Williamsburg where we tested out our tandem stroller for the first time. We got take-out and after Will was down for the night, the three of us had a yummy dinner.

Day 3: Again, we drove the Colonial Parkway, but this time, toward Jamestown. We stopped at one of the stops on the way there and had the whole beach area to ourselves. We dipped our toes (and ankles) in the water and Anna had so much fun playing with just a stick and sand. Then we checked out Williamsburg Pottery and it was nap time for all of us. That evening we shopped at the outlet and got take-out again.

Day 4: We packed up and drove home. We made a pit-stop at IKEA, and lucked out that kids eat free on Tuesday.

Traveling with kids is never easy. Sometimes I think it's easier to just stay home and never go anywhere. This trip was no exception. However, hubs and I both agreed that this was our best Williamsburg trip yet. I love spending time with my family without any distractions or worry about what to cook for dinner!
There are over 200 more pictures here.


  1. sounds like a fun trip. the beach looks refreshing! williamsburg sounds like a quaint place! glad to you had a nice family weekend!

  2. This trip looks so fun. I've always wanted to go to Williamsburg (well ever since I was 10 and ready the American Girls Series).
    Btw, your whole family is adorable. :)

  3. One of the best and most frustrating little trips ever! But am so glad we did it, now where are we going next?

    1. I actually didn't think this trip was that frustrating since the kids were mostly well behaved. It was just a lot of work - lugging them around and them cleaning them when we get home. Definitely good team work required. The only frustrating part for me was Anna's mood swings in the car.

  4. Update for my own record: We stayed at Colonial Crossings Resort, which is now under new management.



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