When to Book School Breaks (and Where to Actually Go)

Family TravelFamily Luxury Travel

Nov 9

Written By Kate Van Dell

By Kate Van Dell for Sebastian Luxe Travel

*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.

Read now: How to Choose Your February or April Break 2026 Destination Without Overthinking It (Even Though You Absolutely Will)

  
    📅 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: 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.

The Best Ski Resorts for Families 2026

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.

Best Places to Visit in Paris with Kids: Starting in Le Marais

Pulitzer Amsterdam Review: A Family-Friendly Luxury Hotel in the Nine Streets

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.

Summer in the Alps: Where to Go for the Ultimate Mountain Escape

Luxury Family Stay at Martinhal Sagres: Wild Algarve Beauty

Fall Break: The Parents’ Secret Weapon

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.

The Sebastian Luxe Travel Guide to St. Barth

Zermatt for the Holidays: Luxury Hotels & Matterhorn Christmas

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 now.

Kate Van Dell