When Should Families Book Winter Travel?

April 4, 2024

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We all want to know the key to cracking this logic puzzle: When is the best time to book winter travel?

You know you’ll be craving a warm-weather adventure in the dead of winter. And you swear this is the year you’ll book your winter travel in advance. Together, we’ll finally make your tropical getaway dreams a reality and learn the best time to book a winter vacation.

Here at Mango Tree Travel, planning trips is a hobby and a career.  We can’t get enough, and the amount of time we spend looking at hotels and flights is a bit embarrassing. 

But for those of you who are not excited to spend hours fine tuning the booking details for winter travel, your dreams of a tropical winter break never make it past a collection of Google tabs and bookmarks.  One of the barriers to booking that travel is sorting through the best time to book winter travel and focus on travel planning. 

As specialists in Caribbean travel for families, we spend a lot of that time specifically thinking about how far in advance to book a Caribbean vacation, as it’s a question we get asked on a weekly basis. 

The short answer: The best time to book a trip is 11-12 months in advance, but we recommend starting your brainstorming and research even sooner. Enter the winter travel booking window with confidence about where you want to go, and be ready to book if you see a deal.
mom trying to figure out when to book winter travel

We asked Sabrina Morrice, a trusted member of our Mango Tree team and avid family traveler, to tell us her tips about the best time to book winter travel for families. 

Break out a notebook or a spreadsheet and let’s begin!

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When and What to Research When Planning a Trip

Before you can determine when is the best time to book a vacation, you have to decide where to go.  

We recommend that families start thinking about winter trips a year in advance. It may sound crazy, but you know when your school breaks will be – and they are the same time as everyone else’s.  

To book a winter vacation with kids you can really get excited about – instead of the last minute “what can I afford” type of trip – start planning early. 

The first step is often the hardest: Research!  The Google rabbit hole of trip planning thwarts the best-laid travel plans.  This initial phase to booking your best vacation is the most daunting, so much so that many families don’t even want to begin. We’re here to help. 

Best Caribbean Snorkeling Resort For Kids

To land on the best winter travel destination, consider first the type of travel and activities you want.

If you’re hitting travel planning indecision, it might be coming from the most fundamental question: Where do I want to go on vacation?

Often, our instinct is to come up with lists of places we want to visit: Italy, France, Belize, Costa Rica!  But perhaps a more subtle question is why do you want to visit those places? 

If you can think about what kind of vacation you want to have first, and then let that inform your destination, you may surprise yourself with where you end up – in a good way. 

Some families are true beach bums at heart. Other families are ready to dive into the local foodie lifestyle of a destination. And still others are all about the cultural hotspots and museums.  Many of us are a blend of all of those things, and that’s great too!  

But also, our wish lists will inevitably change with the ages and temperaments of our kids, and the phases of life we’re in.  (P.S. Have you grabbed our free guide to tackling the Caribbean with kids of every age to help you navigate these changes?) 

We recommend asking this question as you think through each trip: What type of travel experience excites you most, right now? Do you need an easy break, or are you ready for an adventure? 

Once you determine that, focus your destination search with your desired vibe and activities in mind.  There are dozens of great Caribbean islands for families, for example, but some shine for their beaches and snorkeling, while others attract more adventurous travelers with their lush green jungle interiors.  

Rather than start with simply a list of possible destinations to book for your winter trip, start by thinking about what type of trip you want, and then let that list inform your universe of choices. 

Narrow Down Your Choices with Practical Considerations

  • What months am I hoping to go? Is that a good time for the destinations on my list? 
  • What’s my budget I want to spend on the low end and high end? 
  • Are my dates flexible enough to snag a good deal if I find one? 
  • Do I want this to be an easy travel day, or am I willing to go a little further for an adventure for this trip?  How far is the airport from the hotels and activities that are appealing to me?
Travel agents can help parents relax

When is the Best Time to Book Flights for Winter Travel?  

The question when to book flights for winter travel is one we get all the time at Mango Tree Travel, and the answer that no one likes to hear is: it depends. 

The Best Way to Book Flights for Families with School-Age Kids

I wait for the school calendar to drop like a kid on Christmas Eve. The minute I get it, I set up flight alerts and trackers for those dates with flexible starts and ends with my favorite destinations (that advance research pays off here!), so I get alerts of deals when they arise. It’s SO helpful, especially when you have a lot of plane tickets to buy. 

If you read nothing else: we recommend researching your flights for winter travel 11 months in advance

We use Google Flights to start our flight research, and you can start to see available flights 11 months ahead of time, so that you can be ready to book with 6-8 months notice.  Start looking at flights as soon as you can, but focus on early spring for winter travel. 

There are some caveats to our general rules, so let’s get into those.  

Christmas and New Years’ Eve Travel

Planning winter travel for families over the Christmas break presents a unique set of challenges. Many hotels have minimum night stay requirements, and premium pricing.  Plus, hotels often block off their online booking calendars to control the holiday bookings, making the research even harder. 

If you live in a place that definitely feels like winter 3-6 months out of the year, then tropical travel is something that will be high up on your list of must-do’s, and you may want to spend your winter break in a tropical destination.  

The best time to book a Caribbean vacation for the Christmas holiday is 10-12 months ahead of time, which is when hotels release their festive pricing. 

Spring Break Travel 

While not technically “winter travel,” we should address spring break for a moment, since it’s one of the most popular travel weeks for families. 

If you want to head to the Caribbean for spring break – meaning any week in March and April – you are not alone. The best time to book spring break travel to the islands is 10-12 months ahead of time.  That means between May and September of the year before.  

By November, we really notice a decrease in spring break availability for the following calendar year, especially at small boutique hotels with two bedroom suites – which a lot of our clients want with young kids in particular.

Bucket List Travel 

If you are dreaming of a safari in Kenya or a two-week whirlwind trip through Italy, we recommend beginning to research and plan the trip at about the 12-18-month mark, so you know exactly what flights to book when the window opens. 

International travel can require more hoops to jump through, immunizations, and more strategies to ensure you get the most out of your once-in-a-lifetime trip.  Plus, you don’t want to find your dream winter travel destination and hotel, only to find that it’s sold out on your travel dates. For maximum availability, start early.

Family Travel Trends - Group Travel

Large Family Trips 

Planning trips with large families presents a unique set of travel challenges. Most families over 4 people ideally want to secure 2-bedroom suites. This gives you privacy and peace and quiet–especially when you have kids that wake up at different times.  

You should know that, at many hotels, the inventory of 2-bedroom or 3-bedroom suites to accommodate your crew is limited, and those suites go the fastest. In terms of when to book winter travel hotels for groups: Book them as soon as you know where you want to go.  

And if you’re nervous about committing too far in advance, book a refundable rate at a few hotels so keep your options open until flights become available.  

If you need help finding those hotels with the space you need, you can search our in-depth hotel profiles to find the best family-friendly options with the room configuration you need to be comfortable. 

General Domestic Travel  

You can be less of a stickler with domestic flights, but it still pays to book early for better rates! Stick to the 3-8-month window for the best deals, but if you have trouble deciding on a destination, you can still book as late as 2 months before.  After that, flight prices will almost always go up. 

To do some quick math since we’re focused on winter travel, we highly recommend that you book that winter trip by September to get the best flights and accommodations.

dreaming about when to book christmas travel

When is the best time to book a hotel and other accommodations for winter travel? 

There is absolutely no reason to hold off on booking your accommodation once you’ve made a decision about your destination.

That said, let me reiterate a few points made throughout about the best time to book a trip.  

If you want to book a two- or three-bedroom suite, or a boutique hotel with less than 100 rooms, or a bucket list experience – booking early is always key to getting the room you want, at the best available prices. Start researching about 12 months ahead of time, and book a few refundable rooms if you want to keep options open. 

We recommend booking winter travel (Dec-Feb) in early spring of the year before, and the best time to book spring break travel (March-April) is in late spring and summer of the year before.

If you find yourself in need of a last minute winter trip, you’ll always have more luck in destinations with bigger hotels and more inventory.  For example, the best time to book a Cancun trip might be closer to 6 months ahead of time, as there are just a lot more hotels to choose from, and sometimes they offer last minute deals.  Plus, there are near daily flights from everywhere in the U.S.

suitcase packed for winter travel

Let Mango Tree Travel Help Lighten the Load!

We truly believe that planning travel with kids can be easy with the right support, including cracking the code about when to book winter travel. Whether you want to join the challenge in May for DIY planning support, snag a done-for-you-travel guide or to plan a custom trip together, we are here to help!