What’s Your Best Advice for Planning a Great Family Vacation?

updated May 24, 2019
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(Image credit: Samantha Estrada)

As May winds down and summer vacation nears, I realize I have no idea what we’ll do. Sure, our kids have a mix of day camps and playdates scheduled for the summer, but in terms of thinking about a real family vacation, I have done exactly zero planning. In the past we’ve done a mixture of long-weekend car trips and a plane trip to visit family, but this year we are hoping to have one excellent family vacation that is just for us — a destination we haven’t been to before and that definitely doesn’t involve crashing at Grandma’s house.

I’m not even sure where to start with family vacation planning, and that’s where I need your help!

About My Family

Our children are 5 and 2 1/2, with a decent amount of travel experience, but the last time we did a real family vacation (i.e., not visiting family for holidays) my daughter was 2 1/2 and I was pregnant with my youngest. So it’s been at least three years since we’ve organized a real family vacation.

We’re looking for family-friendly destinations and are open to driving, flying, or hopping on a train. We’re not sure whether we should do a vacation rental or hotel, or maybe even camp. (Does that sound like an adventure or a total nightmare?) And then once we’re there and settled, we’ll need a plan for enough activities to make the trip fun and memorable, but not so many that we can’t actually relax.

So, Dear Kitchn Reader, Help a Mama Out!

Do you plan family trips via plane, train, or automobile? Do you go glamping or is booking a kid-friendly vacation rental more your speed? And do my kids need a travel itinerary or am I way over-planning here?

Tell me all your best advice for planning a great family vacation and we’ll share our favorite tips and tricks next week!