School Break Travel Guide 2026: When to Book & Where to Go
Martinhal Beach, Sagres, Portugal in August
Once upon a time, I measured life in seasons.
Now I measure it in school breaks.
There’s Winter Break, Spring Break, Summer Break, and the annual delusion known as “we’ll just stay home this year.”
If you’ve ever tried to book a trip around the school calendar, you know the truth: the second you decide where to go, everyone else has already decided to go there.
But don’t worry. There’s a method (and a little magic) to getting it right.
Here’s when to book what, where to go, and how to make family travel feel truly doable.
📅 Sebastian Luxe Travel: The Ultimate School Break Booking Calendar
| Break | When to Travel | When to Book (For Best Rates) | Popular Destinations |
|---|---|---|---|
| Winter (Feb) | Mid-Feb | July – Dec | Costa Rica, Turks & Caicos, Riviera Maya |
| Spring Break | Late Mar – Mid-Apr | Sep – Dec | Caribbean, European Cities |
| Summer | Jul – Sep | Oct – Mar | Europe, Hawaii, Costa Rica |
| Fall Weekends | Oct – Nov | Jul – Sep | Mexico, US Cities, Short Europe |
| Christmas / NYE | Dec 20 – Jan 2 | Feb – May | Caribbean, Alps, Mexico |
February Break 2026: The Emotional Support Vacation
Seven Mile Beach Perfection, Grand Cayman in February
When to Book: July through December
Suggested Destinations: Costa Rica, Turks & Caicos, Mexico, Aruba, Grand Cayman, Palm Beach, Miami
By February, you’ve hit the wall. The air hurts your face, someone is always coughing, and the word snack has lost all meaning.
This is your reward trip — the official midwinter escape from everything.
Insider Tip: Skip Hawaii in February. It’s lovely but windy, and the water’s too cold for swimming unless you’re part sea lion. Costa Rica, on the other hand, is a masterclass in easy adventure: zip lines, monkeys, and warm pools that make everyone forget about algebra.
Spring Break: The Great Migration
The Ritz Turtle Bay, Oahu, HI in April
When to Travel: Late March – Mid-April
When to Book: September through December
Spring Break is when every family north of Miami collectively decides to flee. Flights fill fast, villas vanish, and you start questioning why school even exists.
Warm Escapes: Anguilla, Cabo, St. Lucia, Riviera Maya, Hawaii, BVIs (The Bitter End just reopened!)
Mild & Cultural: Paris, Rome, Comporta & Lisbon, Amalfi, Amsterdam, London
April in Europe is quietly perfect. The flowers are blooming, the lines are short, and you can tell yourself it’s cultural exposure while drinking rosé at noon.
Pro Tip: Book in the fall. You’ll forget you did, and then Future You will feel brilliant when that confirmation email appears in February.
Summer: The Three-Month Marathon
Avoid the traffic and travel by boat. Positano, Italy in June
When to Travel: July – September
When to Book: October through March
Summer is not a vacation. It’s a logistical puzzle disguised as leisure. You have roughly 90 days to make memories, avoid heatstroke, and keep everyone hydrated.
Europe (Culture & Carbs): Italy, France, Greece, Switzerland, Portugal (Sagres if you want to avoid the heat)
Closer to Home (Easy Flights & Sunsets): Hawaii (ok maybe not the easiest flight but worth it), Costa Rica, California, Maine, St. Barth (in June or July)
September is for the insiders — same sunshine, fewer crowds, better rates.
Insider Tip: Book airfare early, hotels refundable, and your sanity non-refundable.
Fall Break: The Parents’ Secret Weapon
Hydra, Greece in September
When to Travel: September – November
When to Book: July through September
Fall break is travel’s best-kept secret. The weather is still beautiful, the rates are down, and you can pretend you’re being spontaneous.
Shoulder-Season Magic: Mexico, Napa, Greece, Lake Como & Milan, Lisbon
Europe glows, beaches empty, and you can finally get a dinner reservation.
Christmas & New Year’s: The Olympic Games of Planning
Plenty of Bluebird days in Zermatt, Switzerland in December
When to Travel: December 20 – January 2
When to Book: February through May
You think you’re early when you start in September. You’re not. It’s the Super Bowl of travel, where demand for destinations like St. Barth, Aspen, and Anguilla peaks.
Warm: St. Barth, Anguilla, Turks & Caicos, Grand Cayman, Puerto Rico
Cold / Snow: St. Moritz, Zermatt, Aspen, Jackson Hole
The trick is to book early, choose refundable, and check back later for promos.
Pro Tip: If you missed it, travel the week after New Year’s. Same sunshine, fewer humans, better energy.
Sebastian Luxe Travel’s Real Rules for Sanity
• Book flights first. Hotels forgive; airlines do not.
• Always go refundable. It’s the only kind of control we have left.
• Avoid Saturday departures. Everyone else is doing the same thing, and you deserve better.
• Don’t tell the kids until it’s confirmed. Hope is dangerous.
• Call it adventure. It sounds intentional, even when it’s chaos.
Every trip feels impossible until you’re on it.
Then one morning you’re drinking coffee by the water, the kids are miraculously quiet, and you remember why you do all this.
Book early enough to get what you want. Late enough to feel spontaneous.
Start planning and unlock exclusive perks like resort credits and room upgrades. We book these properties all the time and can match you with the spot that actually fits how you travel. If you prefer to double check our credentials, you can peek at my Fora advisor page or Virtuoso profile and read our Testimonials. Either way, we’ll take care of the details so you can focus on the fun.
