It’s the question we hear most often at the office: “should I book now, or wait and see if it drops?” The answer isn’t down to luck — there are booking windows that actually work, and September is when they start to matter.

How far ahead to book

Airlines release flights for sale roughly 10 to 12 months before departure. You don’t need to be there on day one, but one rule holds: fares are usually lower while plenty of seats are still available, and they climb as the plane fills.

Based on Skyscanner’s historical data:

• Short-haul flights (under three hours — Italy, Germany, London, the Balkans): one to three months ahead.
• Long-haul flights (over six hours — the USA, Thailand, Japan): two to six months ahead.

OAG analyst John Grant puts the sensible window between five months and six weeks before travel — the point where airlines have a clear read on demand and often move to fill remaining seats.

The day you book matters

For years the received wisdom was that Tuesday is the best day to book. Expedia’s 2025 analysis, drawing on the ARC and OAG ticketing databases, found something different: Sunday is the cheapest day to book regardless of destination — around 6% less for domestic flights and up to 17% less for international ones, compared with Monday or Friday, the most expensive days.

It’s a small detail, but it costs nothing. If you’ve made up your mind about the trip, leave the booking for Sunday.

Why September is the pivotal month

Here’s the practical part. Holiday trips — Christmas, New Year, winter breaks — share two features: fixed dates and enormous demand. When you have no flexibility on dates, “wait and see” is the worst possible strategy.

If you’re planning:

• Christmas or New Year in Europe: book during September or October.
• A winter trip somewhere exotic (Thailand, the Maldives, India, Egypt): two to six months out, which means now.
• Business or premium seats in peak season: as early as you can — demand here stays consistently high.

When waiting does pay off

There’s a flip side. Because airlines watch demand constantly, a flight that isn’t filling as expected can drop in price close to departure — usually on off-peak days or less popular routes. It’s a high-risk strategy: you might catch a bargain, or you might end up with long layovers or a sold-out flight.

Only play it if you’re genuinely flexible on dates and the destination isn’t one of the busy ones.

Three things we forget

• It’s not just our own holidays. Check whether a local holiday or major festival falls at your destination — fares rise and availability drops.
• Price isn’t the only criterion. A fare that’s €40 cheaper with an eight-hour layover rarely works out.
• Sign up for alerts. Airlines announce new routes and flash sales through their newsletters and social accounts first.

Would rather not think about it at all?

At Penguin Travels & Tours we track the booking windows for you and tell you straight when it’s worth booking and when it’s worth waiting — for departures from Athens, Thessaloniki or Kalamata.

Planning a trip for the holidays? Stop by our office in Kalamata (Vasilissis Olgas 4) or call us at +30 27210 80701 — now is the right time to lock it in.