How we book and plan our big family holidays

Of course, you can always buy a complete package through a travel agency – and that’s a great option for some indeed. But honestly, it doesn’t take that much time to book everything yourself. The big advantage is that you get to choose exactly the hotels you want, the areas you’d like to stay in, and the tours that suit your family. It’s not difficult to organise transport either – most things can be booked online in advance. If it makes you feel calmer, you can book a transfer straight from the airport to your first hotel, or even arrange a rental car waiting for you on arrival. We’ve rented cars in Canada and Mauritius and it worked perfectly.

This guide is about how we plan and book our longer holidays – the ones outside Europe. If we’re heading for a beach holiday in Southern Europe, we don’t go to these lengths. But for Thailand, Bali, Canada or Mauritius and places like this, this is our routine.

We usually start talking about our next big adventure around nine months ahead. Sometimes we already know where we want to go (Thailand, Bali, Canada). Other times, the destination appears after a bit of research and late-night Googling – that’s how Mauritius ended up on our list. Remember to check the weather at your destination for the time you plan to travel – you might want to take rainy season or hurricane season into account for example.

The very first step for us? Asking my parents if they can look after our dog, Bailey. Once that’s sorted, the fun really begins.

Flights first

Flights are the first thing we sort out for our trip. I normally search on Momondo and filter for airlines I feel comfortable with. With a mild fear of flying, it’s important for me to trust the carrier. We never book more than one layover – anything else is too much with kids. Of course, that’s what one would prefer, but one stopover works fine for us.

Sometimes I’ll look at where the stopover is and whether we could turn it into a mini-break. It often costs the same to stay a couple of days. Once I’ve found the right route, I keep an eye on prices. If they drop, I wait; when they rise again, I book. In my experience, the sweet spot is around six months before departure.

We usually book the “non-refundable but changeable” tickets. They’re cheaper, and we’re happy to pay a smaller fee if we need to move dates or destination.

The fun part – hotels and planning

Once flights are booked, I can relax into the fun bit. I’ll watch YouTube videos while cooking or working out – they’re a great way to get a sense of where to stay and what to see.

We love splitting our trip between several locations. If we’re away for 15 nights, we’ll often book three different hotels – five nights in each. It keeps things varied, and we get to see more. Sometimes we add an Airbnb with a kitchen so we can cook a few meals ourselves and save money.

For hotels, I mostly use Booking.com and always book options with free cancellation. It’s worth checking carefully before paying, but that flexibility is invaluable if plans change.

The practical stuff

Don’t forget the less glamorous parts:

Airport parking: it sells out and gets more expensive closer to departure. Book it as soon as you’ve got flights. You can usually change the number plate later if needed.
Vaccinations: check which ones are required for your destination, and some need to be taken at specific times – book appointments well in advance.
Travel insurance: make sure it covers the type of trip you’re taking, especially if you’re planning activities like hiking or water sports.
Luggage rules: oh yes, always a bit of a jungle! Check with your airline for size and weight limits.
Check passports, visas, and any required apps; for instance, we filled in ArriveCAN before visiting Canada.

Before we go

We’re not obsessive planners well okay maybe a little obsessive, but you don’t need to be. I’ll usually make a note on my phone with a the must-see sights, maybe look through a Lonely Planet, and write down ideas from YouTube or blogs. If it’s high season, we might pre-book tours, especially the popular ones. Otherwise, we prefer to stay flexible and pick things up as we go, chatting to locals or other travellers.

Our best tips for booking a long holiday – a total guide

Start early – ideally 7 months ahead, especially for longer holidays with children.
Pick your season wisely – check for rainy seasons, hurricanes or extreme heat before deciding.
Sort practicalities first – pets and/or house sitters.
Flights matter – use comparison sites, stick to airlines you trust, and avoid too many layovers.
Watch prices – track them for a while; often 6 months before is cheapest.
Check cancellation rules – understand exactly what you’re booking.
Think about layovers – sometimes it’s worth adding a couple of days.
Hotels – use sites like Hotels.com, aim for flexible booking, and split longer trips across different areas for variety.
Add an Airbnb – a kitchen can be a lifesaver with kids and saves money.
Book airport parking early – cheapest spots sell out first.
Vaccinations and insurance – check requirements well ahead.
Pre-book key attractions – if it’s peak season or a popular sight, do it before you go.
Get inspired – YouTube, podcasts, blogs and guidebooks are easy ways to collect tips.
Stay flexible – leave some days unplanned to explore spontaneously.
Transport – don’t stress, most transfers or rentals can be booked online in advance.

I hope this gives you some inspiration to plan and book your own holiday instead of going through a travel agency. It’s easier than you might think and doesn’t have to take long. Enjoy the process, and feel free to send any questions you have!

Already read our in-depth guide? Here’s the quick checklist for your trip

Travel Tips

The Complete Guide to planning and booking your own Family Trip