Your Family’s 2026-2027 School Break Travel Guide
Globe Trotter
Back to school usually means back to routines. Drop-offs. Practices. Homework. And a family calendar that somehow fills up before September is even over.
But hidden between all those school days are some surprisingly good opportunities to get away.
A three-day weekend can become a fall escape. Thanksgiving break can trade hosting duties for poolside lounging. Winter break gives you enough time to finally take that bigger family trip. And spring break? Well, there's a reason everyone starts dreaming about sunshine by March.
So before the school year gets away from you, pull up your district calendar. We've mapped out the major travel windows for the 2026-2027 school year, plus a little inspiration for what your family could do with each one.
Exact school break dates vary by district, so always check your local school calendar before making travel plans.
October Long Weekend: Chase Fall While It Lasts
Indigenous Peoples' Day: Monday, October 12, 2026
School has barely settled into a rhythm and there's already a long weekend on the horizon.
For families whose schools close for Indigenous Peoples' Day, three days is just enough time for a change of scenery without taking extra days away from school.
This is fall's moment to shine. Head to New England for changing leaves, cider doughnuts and crisp afternoons spent outside. Vermont's small towns make a classic foliage escape, while Boston gives families plenty to do in the city with autumn scenery within day-trip distance.
The trick with a long weekend is keeping the journey manageable. Choose somewhere you can reach relatively easily, pack light and save the ambitious itinerary for a longer school break.
The travel idea: A New England fall getaway filled with foliage, small towns and plenty of reasons to order another cider doughnut.
Thanksgiving Break: Gather Somewhere New
Thanksgiving: Thursday, November 26, 2026
Thanksgiving can mean family traditions, a packed house and a kitchen that somehow produces dishes faster than anyone can wash them.
Or, every once in a while, it can mean leaving town.
Many school districts build additional days off around Thanksgiving, potentially creating a useful family travel window without missing much, if any, classroom time.
If your family's open to swapping the traditional celebration for something different, consider an all-inclusive Caribbean getaway. You can still gather around the table together. It just might come with an ocean view and, even better, no meal planning.
Because Thanksgiving is also a popular travel period, this isn't one to leave until November. Once your school's calendar is confirmed, it's worth getting plans moving.
The travel idea: Trade cooking, hosting and cleanup for a Caribbean all-inclusive where family time is still the main event.
Winter Break: Make This the Big One
Christmas Day: Friday, December 25, 2026
New Year's Day: Friday, January 1, 2027
If there's one school break that deserves a bigger circle on the calendar, it's this one.
Winter break is typically one of the longest stretches families have together during the school year. That makes it an opportunity to take the kind of trip that doesn't comfortably fit into a three or four-day weekend.
A longer cruise is a natural match. With more days available, there's time to settle into life on board, explore multiple ports and still have those gloriously unplanned afternoons when nobody needs to be anywhere.
It's also one of the year's most popular travel periods, which means flights, accommodations and popular itineraries can fill well in advance.
If winter break is going to be your family's big trip of the school year, make it one of the first you plan.
The travel idea: Take a longer family cruise and experience multiple destinations together, all in one vacation.
January Long Weekend: Find a Little Winter Sunshine
Martin Luther King Jr. Day: Monday, January 18, 2027
By January, the holiday decorations are packed away, school is back in session and summer can feel very far away.
Enter the three-day weekend.
For families with the day off from school, Martin Luther King Jr. Day weekend can create a quick opportunity to reset after the rush of the holidays.
Florida is an easy place to look for inspiration. A few days at a theme park can deliver plenty of excitement without requiring a full week away, while a warm-weather resort gives everyone a chance to trade winter coats for swimsuits.
With a shorter break, think less about seeing everything and more about choosing one thing your family will genuinely enjoy.
The travel idea: Head south for a few days of Florida sunshine, whether your crew prefers roller coasters or pool chairs.
Presidents Day and Midwinter Break: Go Find the Snow
Presidents' Day: Monday, February 15, 2027
This is where checking your individual school calendar really pays off.
Some districts observe only the Monday holiday, while others build a longer midwinter break around Presidents Day. That could mean anything from a quick three-day escape to an entire week waiting to be filled.
And since it's February, you might as well embrace winter.
A mountain getaway gives families plenty of ways to play in the snow, even when not everyone is ready to tackle a black diamond. Skiing and snowboarding can share the itinerary with tubing, skating, hot chocolate and a cozy evening back at the resort.
If your district gives you the full week, consider traveling a little farther. If you've only got the long weekend, look for a mountain destination that's easier to reach.
The travel idea: Turn midwinter break into an actual winter break with a few days in the mountains.
Spring Break: Follow the Family to Sunshine
Typically March through April 2027
At some point during a long winter, sunshine stops sounding nice and starts sounding necessary.
Hello, spring break.
Dates vary considerably across U.S. school districts, with many breaks falling between mid-March and mid-April. That makes your school's calendar more important than any national list.
Once you know your week, you can start thinking about what kind of escape fits your family.
An all-inclusive resort in Mexico can make an especially easy family getaway. Kids can move between pools, activities and the beach while the grown-ups enjoy not having to plan every meal or manage multiple schedules.
And for families traveling with children of different ages, that flexibility matters. The ideal vacation for an eight-year-old and a 16-year-old may look very different. A resort with enough choices gives everyone room to find their version of fun.
Spring break is also one of the busiest family travel periods of the year. Once those district dates are official, don't wait too long to start planning.
The travel idea: Swap backpacks for beach bags at a family-friendly all-inclusive in Mexico.
Memorial Day Weekend: Start Summer Early
Memorial Day: Monday, May 31, 2027
You can almost see summer from here.
Memorial Day weekend is the unofficial beginning of the season, and in 2027 it gives families a three-day weekend to celebrate making it through another school year.
You don't need a major vacation to make this one count. Pick a classic beach town, spend a few days exploring a national park or pack up the car for a road trip somewhere the family hasn't been before.
Think of it as the preview rather than the main event. A few days away can satisfy that first itch for summer travel while the bigger vacation is still waiting on the calendar.
The travel idea: Take an easy U.S. road trip or beach escape and give summer an early start.
Your School Calendar Might Be Hiding More Vacation Time
Federal holidays are useful starting points, but they're only part of the picture.
Teacher workdays, district holidays, midwinter breaks and other days off can create extra travel opportunities throughout the year.
Some may even fall next to a weekend or holiday, giving your family more time to get away without missing additional days of school.
Take a few minutes to look through your district's 2026-2027 calendar and map out the days your kids are out of school. Knowing your available dates early gives you more time to explore where you could go, find a trip that fits your family and start planning before popular travel periods fill up.
Once you have your dates mapped out, an Envoyage ASTA Verified Travel Advisor can take it from there. From finding a destination that fits the time you have to bringing all the details together, your advisor can help turn the next school break into a family trip everyone can look forward to.
