Planning a Family Vacation

When I was a kid on vacation with my parents, our trips were action packed. New adventures at every turn! When I became a teen, this became a problem. I just wanted to lay out by the pool. That continued until a couple of years ago when we went on our first family vacation with our own kids. There were no plans other than drive to the vacation location, swim in the hotel pool, and drive home. We spent hours sitting around watching the kids beat each other up and saying to each other, “We should go do something.” But we had no idea what to do! The others on our trip suggested activities like wine tours and cheese tastings. Ummm. Do you want to bring my 2-year-old and infant?

So last year I came up with a jam-packed itinerary. Better to over plan the vacation than sitting around with nothing to do, I thought. I felt kind of silly sharing it out with everyone but I was very clear. This is what I have planned for our family. You are welcome to join us but we understand that these activities are not for everyone. Let us know if you’re interested in any of this so that we can be sure to make proper accommodations. And it turned out great! There was only one thing we decided not to do because we were so dang worn out from all the other stuff. We had decided to stay back and swim instead. Still fun!

I’m planning to jam pack the itinerary once more for this year’s trip, but factor in a packed lunch each day for the kids. Last year we tried to lunch them at cafes and restaurants but they hardly ever ate what we ordered them. It’s like throwing money down the drain. Why go through that headache again? Remind me to put lunch sacks on the packing list!

Anyway, I’m sure there are millions of ways to do this, but here’s how I make plans.

Step 1: Pick a Place. This is easy because it’s not just a family vacation that I’m planning today. It’s a FAMILY VACATION. Kind of like a family reunion on my husband’s side and this will be our third annual trip. So I know we are going to Door County. Done. Check.

Step 2: Follow the town on all social media. This is an ad I saved from the city guide I picked up on our trip last year.

I suggest following the town way before planning your trip. As you hear about activities you are interested in, follow those too so you can get as much info as possible. You can even let them know when you will be in town and ask if they have any specials going on. Get communicating with these places on social media. They love that stuff. You can find all kinds of things on social media. Reviews from previous guests, hidden gems, news updates, road closures, etc. Personally, I opened up my twitter a few weeks ago and not only followed Door County, I followed each town, a couple of news outlets, the resort we stay at, and a number of restaurants, fun parks and activity centers that I know we are interested in checking out this year. Then I watched for updates about things going on this summer and other key information that I will use when planning our itinerary.

Step 3: List out all the things you want to do on post-its. I like to move them around in my planner later so I use these tiny tab post-its. I put each activity on one post it and line them up in no particular order.

Step 4: Sort activities by day. I start grouping activities by day based on their location and amount of time they take. Then I spread the activities out through the day. If I have any big holes in the plan, I look up additional activities, but usually, I have extra activities. I keep those to the side in case plans change. It could be rain, it could be a closure, you never know. It’s always best to have some alternate activities in your back pocket. I try to work in a lunch spot every day but I’m not going to sweat it if I have days that have holes in the planning. There are plenty of other things to do in Door County to fill up the days. I schedule our days like this so that everyone knows ahead of time what we are planning. That way we don’t sit around and stare at each other until we come up with something to do.

Step 5: Keep it real. Be realistic about how much you can actually do on your trip. You might have to save some things for the next time you go. If it’s a once-in-a-lifetime trip, try to do as much as you can but remember that sometimes, you just want to lay out by the pool. And that is what vacation is all about. Doing what you want to do.

What kind of vacation do you like to take? Where have you gone with your family and how do you plan for trips? I’d love to hear your stories!