Cape Charles Family Vacation

Today we are sharing a little bit about our Cape Charles family vacation that we just got back from with Michael’s family.

Choosing a location for Family Vacation

We were put in charge of finding a place to go for a family vacation. Michael’s sister and her whole family lives overseas and is just back for the summer and so we wanted to be able to get away together for a week. 

Because we weren’t sure of timing for when she would be back in the US we waited until pretty close to the summer to start planning. So a ton of things weren’t still available but we did find this really cute home in Cape Charles, which is on Virginia’s Eastern Shore. 

It was Michael’s parents, Michael’s sister and her family (which is her husband and two kids), and then our family. So there were six adults and three kids. We need to find somewhere that would fit all of us and was very kid friendly. 

So we were looking for some thing maybe by the water or some sort of entertainment that would keep the kids busy all day. And we found Cape Charles. We actually shot a wedding there this year. And know about Cape Charles through Young House Love who we follow on Instagram and who used to have their own Airbnb in Cape Charles.

It ended up being the absolute, perfect, ideal location for families with really little kids. 

Cape Charles Family Vacation

The first day we were there, Nick (Michael’s dad), went on a bike ride and came back and told us about the beach before any of us have been there. He said “you have to walk forever to actually get to the water”.  We didn’t really understand what that meant, but we walked up and truly you can walk for 100 yards and still the water will be at your knees.

At low tide you can get all the way to the buoys for where the boats can go, and you could still be just with the water at your waist. 

So to go to the beach with two kids under two years old it was perfect. We could just let them run and play and feel safe with them being in the water without being pummeled by a wave. And they had such a blast because they had some freedom and independence where we didn’t have to be constantly holding onto them.

Specially at low tide, there were just a ton of title pools where they could splash around in fall over and play in the water.

Cape Charles Town

So that was great but it was also a really cute little town. The whole area was maybe a 10 blocks square.  It is really small in a big golf cart town. Everybody seemed to have a golf cart. But we didn’t get one and were totally fine with just having a car.

So much open free parking on the street at the beach and it really didn’t matter. I think every day we got to the beach at a different time and we’re still able to park almost right next to the beach entrance.

There was a cute little hotdog stand right outside the beach entrance, bathrooms were available, and there was a fishing pier which Michael and his dad took advantage of one day. Niles had to stay in his stroller because the pier was a little precarious in places.

There’s also a strip of tons of cute little restaurants. An ice cream shop with insanely good ice cream it’s like nationally ranked. And they were bike paths everywhere to be able to walk around.

Oh thirdly (we had the beach, the cute little town) and then there was also a cute little park in the middle of the town with an awesome playground and open area where the hold events and stuff. 

Cape Charles Restaurants

One tip if you are planning to go out to dinner on your Cape Charles family vacation, is that you need to plan to have a bit of a wait time. We made a big list of restaurants in advance that I had research and heard that were good so we had some ideas, but I picked out 3 different ones to go to.  

The first was a brewery, and it was great.  It was actually on the drive up to town so not in the same little strip in town. And it was great – we went really early and there was still quite a bit of a line but they were games and picnic tables outside so we were able to keep the kids entertained while we waited for our meal.

The next time we tried to go out, it was a restaurant right on the pier in the marina. We walked up to the hostess and she told us that we get two hour wait. (Which seemed like was kind of the same story everywhere we tried).

I tried to call to make a reservation but it seems like none of the restaurants in town take reservations. So definitely if you’re traveling there especially with a larger group make sure you plan accordingly.

Cape Charles – Airbnb

Finally, the place we stayed was an Airbnb.  It was perfect for our Cape Charles family vacation because obviously the owners have kids.  There were beach toys, and high chairs, and so many things that we wonderful to have/not have to pack. 

It was a little bit of a smaller home but worked really well for us. The only thing that I would’ve changed is that in the listing there was a dining table that had six chairs.  We thought, OK perfect, we have six adults. But didn’t really factor in where the kids would eat. So that ended up being a little bit of an issue.

I would definitely suggest taking a look at how you were going to do your meals before booking a Airbnb or place to stay. 

Vacationing with a Toddler

So what made vacationing with a toddler easier. What did we do well?

I think having a place that was really close to entertainment and in our case the beach worked out really well. We were able to go back-and-forth for meals or naps without any trouble. Being so close with free parking made it easy to be flexible with a toddler.

I would have said how we scheduled everything out.  My family is super organized when we go on vacations and send out a Google Doc in advance to make sure that we have everything planned so when we were in charge of planning for the Archer family I sort of did the same thing.

I did so there was a day where each of us had a meal to cook for everyone and then picked out a few places to go out to eat to fill in the other days. I made a grocery list where everyone could add items they were going to bring or some thing that they wanted from the store. And it helps with space in the fridge and freezer.

And I think it just makes it easier with a large group of people to have some sort of plan and organization so that we’re not all asking what is it they were supposed to be doing.

Beach Vacation with a Toddler

Also we planned out some good toddler snacks and meals to take to the beach so that we were able to stay at the beach a little bit longer and not feel like we had to rush home for those things. So we froze to-go yogurts, and freezing apple sauce packets, that kind of thing. 

We also didn’t bring a lot of things with us to the beach, so that made it easy to come and go as well. If you know us, you know we are pretty minimalistic in our parenting, so it’s not surprising. 

We also had lunches where the other families babysat so we could go out on our own for a date – which I think worked really well. 

What do you think we probably should’ve done better?

Probably should’ve booked earlier so we could’ve had more variety at our choices. 

We had a wedding on each side of the vacation – so we would have changed that, but otherwise it was a wonderful trip! 

Let us know if you have any questions about our Cape Charles family vacation! 



Cape Charles Restaurants

Deadrise Pies – Great pizza place in town.  We picked up and took it back to our house for dinner. 

Shanty – This is the restaurant we went to with the 2 hour wait. We ended up going the next day for lunch and sat at the outdoor bar (with no wait).  It was delicious and beautiful!

Brown Dog Icecream – Will definitely have a line, but you can also order a pint and skip the line. Named one of the “Top 10 Best Ice Creams in America” by TripAdvisor.

Coastal Baking Co for DELICIOUS pastries and sandwiches. 

Cape Charles Brewing Company – Mostly picnic tables outside with some games to keep the kids entertained.  You order at the window inside and they will text you when it’s ready to pick up.

We went to Kiptopeke State Park, but I wouldn’t really recommend it.  It’s a national park, so there is an entrance fee and I thought the beaches were just as good in Cape Charles without the drive.

Our Airbnb can be found here. It was wonderful and very family friendly!

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