How to Plan Family Trips Around the School Calendar

Contrary to popular belief, you don’t need to pull your kids out of school to travel internationally. A typical American school year includes somewhere between 8 and 10 weeks off outside of summer, spread across Thanksgiving, winter break, a February break in some states, spring break, and a handful of three-day weekends. The work is matching the right kind of trip to the window you already have, and being willing to look at months other than June and July.

We’ve taken our three school-aged kids to 24 countries and 36 states, all on a regular public school schedule.

Here’s how the calendar math has worked for our family.

How many school days will my kids actually miss?

Two or three at most, and usually only before a break. We do sometimes miss school days. The most my girls have ever missed is 2 or 3 days before a break, and maybe 1 day on the back end.

We don’t pull them for a week and we certainly don’t plan a trip and then figure out the school situation later.

I like to take a Thursday departure instead of a Saturday one so I can turn a 5-day break into 9 days on the ground. That’s the difference between “we could do Florida” and “we could do Europe.”

So when I say we travel on the school calendar, I mean we treat the calendar as the starting point and then look for the two or three days at the edges that make the window work when needed. This also sometimes helps to give us cheaper flight options.

That’s a very different thing from pulling your kids out. And it’s a lot more doable than most parents think.

How much time off does the school year actually give you?

Between 8 and 10 weeks, once you count everything that isn’t summer. Before you pick a destination and before you open a single flight search, print your district’s calendar…or pull it up on your phone, and mark every window longer than three days. Then count them.

Here’s ours in New York, and yours probably looks similar with a few differences:

• Thanksgiving: 5 days
• Winter break: 1 to 2 weeks
• February break: 1 week
• Spring break: 1 week in March or April
• Summer: July and August
• Long weekends: Indigenous Peoples’ Day, MLK Day, Memorial Day

That’s a lot more travel time than “we only get summer,” which is what most families tell me when they first sit down with me.

And notice that there’s no week where the trip magically becomes easy and cheap and uncrowded. Every window has a tradeoff. You’re just picking which one works best for your family.

Need help on when to book flights, hotels, etc.? Check out my free school break planning tool here:

What kind of trip fits in each school break?

It depends entirely on the length of the window, and that’s the question to start with. I stopped asking a general “where should we go” and started asking “what fits in the days I have.”

This is my whole system in one line.

Where can you go on a 3 or 4 day weekend?

Drivable, or one direct flight works best. This is where a lot of families waste the window entirely, because a long weekend doesn’t feel like a real trip, but it is. It’s just a different kind. A city you’ve never seen. A national park a few hours away. Somewhere your kids can be somewhere new by dinner.

I wouldn’t recommend flying six hours for a three-day weekend. You’ll spend a third of the trip in transit and everyone will come home worse than they left.

What can you do with a 5 to 9 day school break?

More than you think. The Caribbean, Mexico, a cruise, even Europe if you stretch the edges. This is the sweet spot, and it’s the window most families underuse.

With a Thursday out and a Sunday back, a 5-day break becomes 9 or 10 days. Now you’re looking at the Caribbean, Mexico, a cruise, Europe, or a domestic trip somewhere far away from home.

This is also where cruises earn their reputation with families. Everything’s included, nobody’s packing and unpacking, and the itinerary is built for you. If you’ve got one week and you want the least logistics for the most trip, a cruise can be the answer.

How long do you need for Europe, Asia, or Africa?

Ten days minimum, and closer to two weeks if the flight alone eats a full day on each end. Now the long-haul math starts working to places like Europe, Asia, or Africa. The trips where the flight alone eats two days.

In my opinion, a 14-hour flight is not twice as hard as a 7-hour flight. It’s roughly the same amount of hard, spread over more hours. What determines whether a long-haul trip works is how many days you have on the other end. Two weeks makes a 20-hour travel day worth it.

Is February break a good time to travel with kids?

It’s the best week on the calendar if your district gives you one. Most of the country doesn’t get this week, which means February pricing on flights and hotels stays reasonable in places that are unaffordable in July.

We went to Tanzania in February. We didn’t go because it was the only week we had, but because February is calving season in the Ndutu Region, and roughly 8,000 wildebeest calves are born every single day during that window. That’s not something you can see in July. That’s just knowing when to go and having a week that lines up.

We’ve also done Arizona and New Mexico in February, which is the correct month to be in the desert. Everyone else is going in spring and paying more to be hotter.

Two very different trips over the same week, but both are better in February than they would have been at any other point on our calendar.

Is spring break worth it if you want to avoid crowds?

Yes, as long as you’re not going where everyone else goes. Spring break has a reputation problem, and it’s mostly deserved if you’re going where everyone else goes.

We did Greece and Croatia over spring break, before the summer crowds arrived. The weather wasn’t beach weather. It was better than that. Empty sites, restaurants that had time for us, and prices that hadn’t turned over into peak season yet.

The Mediterranean in April is one of the most underrated family travel windows there is. Everyone’s picturing August. April is the same place with a third of the people (and almost half the price!).

Should you save your big trip for summer?

Only the trip that can’t happen any other time. June through August is the long block most families have off, and it’s often where our biggest trip goes.

I’m not going to pretend otherwise. June through August is the long block most families have off, and it’s often where our biggest trip goes.

This summer that was two and a half weeks through Singapore, Hong Kong, Shanghai, and Beijing, finishing a Disney castle quest I’d been chasing for 15 years. There’s no way to do that trip over a 5-day break. It needed the long summer break to make happen.

I know, I know. Summer is also the most expensive and most crowded time to be almost anywhere, and it’s the only window where you’re competing with every other family in the country. So here’s how I think about it, summer gets the trip that can’t happen any other time. Everything else gets distributed across the windows where we’re not paying peak for the privilege of standing in line.

But I get it, between sports and other family requirements, summer is often the only time you can travel. Just go in with a plan and know what to expect, and it’ll be fine.

When should you book a trip over a school break?

Nine to twelve months out for anything international. Every family in your district is looking at the same week you are, and the best flights and properties go first. My international trip prep checklist can help you determine everything you need to do once you’ve picked your travel window.

Does the month you travel matter more than the destination?

Sometimes, yes. Disney in October and December isn’t a compromise as those are the months with the holiday parties. The calving season trip only works in February. Greece without crowds only works before June. Before you decide a window is too short or too inconvenient, ask what that month is good for. Sometimes the answer is better than the month you were hoping for.

The school calendar does you a favor

Planning around a school calendar isn’t a limitation. It works like a filter. It forces you to book earlier, which gets you better prices. It pushes you into shoulder seasons, which gets you fewer crowds. It rules out the lazy default of “let’s just go somewhere in July,” which is how most families end up spending the most money for the most crowded version of a trip.

Our kids haven’t visited 24 countries because we found a loophole. We got there because we stopped waiting for a window that doesn’t exist and started using the ones that do.

Your calendar is already on the fridge. Go count the weeks.

Want help mapping your year? The free School Break Planner walks you through your district’s calendar and shows you what fits in each window.

Planning something bigger? I’m a family travel advisor and this is what I do all day. Cruise planning is complimentary, custom trips start at $250, and a 1-hour consult will get you unstuck if you’re doing it yourself.