Booking far in advance or waiting for sales — what really pays off for a family?
This is THE question everyone is asking. Travel agencies will tell you to book early. Bargain forums will tell you to wait until the last minute. The truth? Both are right—but not for the same types of trips. After years of family travel, here’s what we’ve learned the hard way… and to our advantage.
Rule number 1: It depends on the type of trip
There is no universal answer. The real question is: What exactly do you have in mind? A la carte flight + hotel, or an all-inclusive package to the South? The strategy is completely different depending on the answer.
Flights, hotels, and custom trips: book early, always
For everything related to dry flights, independent hotels, car rentals, or tailor-made trips — Booking far in advance is almost always a win., especially with family.
Here's why:
Flight prices go up over time. Airlines use algorithms that adjust prices in real-time based on demand. The fuller the plane gets, the higher the fares climb. Traveling as a family, you need 3, 4, or 5 seats together – and that becomes very expensive at the last minute if adjacent seats are still available.
Good hotels fill up quickly. Especially during peak season (summer, spring break, Christmas). A hotel with a pool, well-located, at a good price? It's often booked up months in advance. What's available at the last minute is rarely the best choice.
Peace of mind has value. Going on vacation knowing everything has been confirmed for a long time is a luxury in itself when traveling with young children. Less stress, more excitement.
Our rule of thumb:
- Transatlantic Flights (Europe): 4 to 6 months in advance
- Flights to the South from Montreal: 2 to 4 months in advance
- Popular hotels during peak season: 3 to 5 months in advance
- Car rental as soon as the trip is confirmed — prices are going up a lot
All-inclusive in the South: last minute can really pay off
Now, we're entering territory where travel agencies won't always agree with us — but experience speaks for itself.
For all-inclusive packages, true last-minute deals can be spectacular.
And when we say last minute, we mean true Last minute — 24 to 48 hours before departure, not 3 weeks. Resorts with unsold rooms at D-1 or D-2 prefer to fill them at bargain prices rather than leave them empty. This is an economic reality that tour operators know well, even if they don't shout it from the rooftops.
Why does it work with all-inclusive specifically?
Because with an all-inclusive package, you don't have to organize anything once you're there. No restaurants to find, no activities to plan, no car to rent. You arrive, you drop your bags, and you're off. The preparation time can therefore be almost nil – ideal for jumping on a last-minute deal without stress.
The conditions for it to work:
- You must be flexible on destination — you take what's available, not necessarily your dream spot
- You must be free to leave within 24 to 48 hours — it's not always possible with school or work
- You must have half-packed suitcases mentally — for all-inclusive in the South, it's not complicated
- You monitor platforms like Transat, Sunwing, Air Canada Vacations and Facebook groups for travel deals
What agencies won't always tell you:
Travel agencies have every interest in making you book early — it secures their commission and their planning. It's not that they're lying, it's that their business model favors early booking. True last-minute deals (day before, two days before) are often best handled directly on tour operators' websites or through online deal-watching groups.
The honest summary table
| Type of trip | Winning strategy |
|---|---|
| Dry wine | Early - 3 to 6 months in advance |
| Independent hotel | Early — especially during peak season |
| Car rental | As soon as possible |
| All-inclusive South (resort) | Very early OR very last minute (D-1/D-2) |
| Family cruise | Early – family cabins go fast |
| Europe in an apartment | Early birds get the good Airbnbs. |
Our final advice
If you have flexibility in your life and all-inclusive deals in the South suit you, keep an eye out for serious last-minute offers. Not the «sales» from 3 weeks before when agencies call last minute. The real bargains are 1-2 days before departure, when tour operators absolutely need to fill the plane.
For everything else: book early, sleep better, and really enjoy your vacation instead of spending the last few weeks stressing about availability.