Family vacations are some of the best memories you’ll make together, but once kids are in school, travel suddenly comes with new layers of planning. School calendars, crowded attractions, and peak-season prices can all complicate the fun. But planning trips around school breaks and holidays can be done.
With a little strategy, you can make the most of those built-in breaks without blowing your budget or losing your sanity. Here’s how to organize trips that fit your family’s schedule and create lasting memories.
Map Out the School Year
Start by looking at your children’s school calendars as soon as they’re available. Mark out:
- Major holidays and seasonal breaks
- Teacher workdays or professional development days
- Early-release or half-days that might tie in with a long weekend
Pro tip: If you co-parent or need to coordinate with grandparents, sync everyone’s calendars early so no one is caught off guard. This can be especially helpful for long weekends. It took us far too long to put our plans in a shared calendar. We used to double book ourselves sometimes!
Match Trips to Break Length
Not every break calls for the same style of trip. Think about what suits the window you have:
- Long breaks (summer, winter, spring): These are perfect for big adventures. Think international destinations, national parks, or long road trips.
- Medium breaks (4–7 days): Great for a beach escape, ski trip, short cruise, or visiting relatives in another state.
- Mini breaks (1–3 days): Stay closer to home. A quick city getaway, nearby amusement park, or state park can be just as memorable.
Choosing trips that fit the length of your kids’ time off helps everyone stay relaxed and enjoy the experience.
One other thought to consider when deciding how much time you have, remember that you might want a buffer day at home before you need to go back to work and/or school. We often like having that time to settle back in and get plenty of rest after all the travel.
Book Early but Keep Flexibility
Peak travel times mean higher prices and limited availability, so aim to book as early as possible, especially for flights and popular family accommodations.
One risk of booking too early, however, is that there’s a higher likelihood that your plans need to change. To protect yourself from changes (like a revised school calendar or illness), look for:
- Refundable hotel rates or “book now, pay later” deals
- Airlines with no-change-fee policies
- Fare alerts or deal trackers to snag discounts during peak weeks
A little flexibility ensures you won’t be at a total loss if plans need to shift.
Pro tip: If you will need a rental car for your trip, book it early, then repeat your search every once in a while. Most car rentals don’t charge you anything until you pick up the car, so if you find a better rate closer to your rental date, you can simply book the lower rate and cancel your original reservation.
Budgeting for Peak Travel
Planning trips around school breaks and holidays often means paying premium prices, but a few tricks can soften the blow:
- Travel a day before or after the day the holiday starts and/or ends if your schedule allows.
- Choose lesser-known destinations (or less touristy regions of popular spots).
- Compare vacation rentals, hotels, and even home swaps to see what offers the most value.
- Pack snacks and simple meals to cut down on expensive restaurant stops. Read more about saving money on food here!
These tweaks keep costs manageable while still letting you enjoy peak-season adventures. We sometimes save a good amount of money just by searching flights a day or two earlier or later.
Make the Most of At-Home Breaks
Not every holiday needs a plane ticket. Some of the best memories happen close to home:
- Explore local museums or aquariums
- Try a “tourist in your own town” day and visit attractions you’ve never made time for
- Set up a backyard camping adventure
- Join seasonal community events, like pumpkin patches or holiday parades
These low-key options can be perfect for shorter breaks or when you’re saving for a bigger trip later in the year. Whenever we feel like we are stuck in a rut but don’t have enough time to go far, we look for a new hiking trail or any space with green and water that we can plan a picnic and have a mini adventure. Even when we don’t go far, we always have a good time!
Sample Planning Timeline
A little structure goes a long way. Here’s a simple roadmap to keep you on track:
- 12 months out: Check the school calendar and brainstorm destinations
- 6–9 months out: Book flights and accommodations, and request any time off from work
- 3 months out: Reserve activities, special meals, or childcare if you’ll need it
- 1 month out: Confirm logistics, get your travel gear, prep entertainment for kids, and finalize packing lists
Having a clear timeline helps spread out costs and minimizes last-minute stress.
Planning Trips Around School Breaks and Holidays FTW
Sure, it’s when most of the rest of the world is also planning their own family trips, but it doesn’t have to feel overwhelming. With early prep, a little creativity, and a flexible mindset, you can make every break from quick weekends to big summer adventures something your kids will remember for years.
Do you have any favorite school-break getaways? Drop them in the comments!
For more tips on stress-free family travel, explore the rest of this blog! Here are some places to go next:
Exploring National Parks with Toddlers
How to Keep Kids Cool While Traveling
Outdoor Activities for Toddlers on Vacation