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The pros and cons of booking your holiday early vs late

By Theodora Taylor Franks on 27th September, 2024

Early vs late holiday booking – when’s the best time to book?

You want a great holiday, at a great price. Naturally.

But will you get a better holiday deal if you book 10 seconds before you get on the plane, or 10 minutes after you get back from your last holiday?

After much deliberation here at Flee Towers, the answer to the early vs late holiday booking debate is of course totally inconclusive.

There are pros and cons to either. Plus, as ever, it depends on the destination you’re looking to book.

Here’s what our team think about early vs late holiday bookings.

Pros of booking early

1 – There may be early booking discounts to take advantage of.  Some hotels and countries like to know what sort of holiday season they might have, and so incentivise early bookings – and particularly through their partners (they won’t tell the whole internet it’s discounted too early!)

2 – You’re pretty much guaranteed your first choice of hotel and room type if you book early. There’s no getting to the hotel and realising you’ve got a great view of a tree, but not the stunning blue water beach just a few metres around the corner. Booking early means you’re more likely to get that million-dollar view, at a better price.

3 – Significantly better flight prices & seat choices. Who doesn’t love an exit row seat, and especially when you’re not paying through the nose for it! Booking early means that you’ll have a better choice of connecting flights, too. This is a huge plus in the early vs late holiday booking discussion. Even if you get a great discount on a hotel, if you pay the difference in a last minute expensive flight, it somewhat defeats the point!

4 – Pay a deposit, then budget over time for the balance remaining. At Fleewinter, we take an upfront deposit, and then the balance is owed sometime between 1 and 2 months before you travel, depending on the destination. So, if you book your trip early, there’s no coughing up the whole holiday price in one, as you would do for a last second booking – just the deposit.  This is a huge pro in the ‘early’ column when deciding over an early vs late holiday booking

5 – More flexibility to postpone, if something changes. Plans change, and we know that. However, with an early booking, there’s more time & flexibility to change the itinerary, or even postpone the holiday if something unavoidable pops up.

Cons of booking early

1 – You may not get any discounts and it can be frustrating if deals do later pop up after you’ve already booked. We totally get that – but remember that your Fleewinter specialist will be working with their partners (and friends!) at hotels to ensure that you’re getting incredible value for money, whenever you book.

2 – You’ve got to wait a while for your holiday – and especially if you’ve paid a deposit, it can feel slightly deflating knowing you’ve got to wait for months to actually travel. But that’s where Fleewinter steps in again – we’ll share loads information, hints, travel tips and our secrets with you from the moment you book, to the moment you step on the plane (and through your trip.) Keeping you as excited about your holiday as we are is part of what we love about our job – and it’s so much easier to do that with Vamoos, too.

3 – Post pandemic concern about having money tied up in a trip that’s months off. Now, we’re the first to shudder and look over our shoulders at the thought of 2020. But, by booking through a Tour Operator, if something changes, then you’ll have someone fighting in your corner. We’ll do our utmost to help you get your money back, or postpone your holiday so that you can still enjoy it later. Plus of course, Fleewinter is fully bonded and our bookings are protected with either ATOL or ABTA.

Hidden beach in Matinloc Island, El Nido, Palawan, Philippines - Paradise lagoon and beach in tropical scenery

Pros of booking late

1 – You could score a wicked discount. We send a deals newsletter every few weeks (sign up here if you want to receive them – we don’t put the deals online!) and many of these are the ‘book now, go now!’ variety. Last minute bookings are great if you’re desperate to get away and want to get the most bang for your buck.

2 – You can hop on a plane last minute and be in the sunshine in a matter of hours! Spontaneity is the new spice of life… and who doesn’t love that whirlwind feeling? Especially in the tail end of the northern hemisphere’s summer when the land is sun soaked and the sea is warm. When it’s a bit rainy and cold at home, it’s glorious to hit the ‘sod it’ button and book yourself a week away.

3 – No planning fatigue – just book and go. Planning a holiday is complicated – there’s a lot of moving parts, and most of them are in another language. So use a tour operator to book your trip. Especially if time is of the essence, then outsource the planning to someone who does it day in, day out. There’s no planning fatigue, no overthinking, no time to weigh up options. Just say yes, and hop on that plane.

Cons of booking late

1 – You won’t have the best choice of hotels or room type – it’s whatever’s left. This is the trade off in the early vs late holiday booking debate.Last minute holidays are a spontaneous joy but they’re also an exercise in compromise. You might only be paying 50% for the hotel, but chances are it’s because they’re looking to sell the last couple of rooms – so you might not get exactly what you want.But that’s a pretty good trade off, if you ask us!

2 – Flight prices can be extortionate. And good lord that can be a kick in the teeth if you’ve been lucky enough to snag some great discounts on hotels only to discover that getting there is going to cost the same overall as if you’d booked months ago.There’s no good solution to this other than to track flights, really – but then if you’re going to do that, you might as well book early…!

3 – You need to pay the whole amount upfront. Rather than an upfront deposit, and then a wait before the balance payment, last minute bookings need securing straight away – which means you’ll need to fork out 100% pretty much immediately.If you’ve nabbed the holy trinity of hotel discounts, great flights and no compromises then you need to buy a lottery ticket too! Otherwise, be prepared to pay everything at once.

4 – Pretty much zero chance of postponing the trip or getting money back if you have to cancel.This is the flip of the early vs late holiday booking coin: if something changes, it’s almost certain that you’ll have to forfeit the holiday cost, as hotels will even be cagey about postponing because they’re unlikely to fill your space at such short notice.This is a risk, but booking late can be worth it if the price is amazing.

Early vs late holiday bookings: which is our favourite?

If you book with Fleewinter, we’ll make sure you have a great holiday at a great price, whether you book early or late. It’s just what we do.

But if we’re honest, we love early bookings, as it means there’s more time for us to take care of the fine details, finesse and the all-important personal touches.

Your holiday is as important to us as it is to you, and the more time we have between booking and departure date, the more time we have to scheme and plot what might make your trip even more special.

Are you an early bird or last-minute traveller?


Written by Theodora Taylor Franks

Top Travel Tip
Booking your holiday early means there's more time for a tour operator to plan the personal touches. While it's a wait between booking and travelling, it's worth it!
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