When to book for Athens trip in May, 2026

Are you asking about the transatlantic flight or just the domestic flights. You might want to sign up with Aegean airlines in order to get e mails announcing seat sales.
We always book the transatlantic flight before looking for Domestic flights in Greece. Aegean often has seat sales around December and into the new year.

Am asking for advice about when to book round trip flights from the US to Athens. Thanks.

I'd start looking the end of this summer, just to get a feel for off-peak season prices. Black Friday thru Cyber Monday may probably have good deals. That's when I purchased airline flights the past two years.

@leonard — Thanks for your suggestion.

That's a serious trip to round up 11 people for a translantic travel. It's different than mine. For me, it ended up almost like an impulse trip as my daughter said to me can do it and cannot do it a few times and then in the middle of Feb after I was pondering other plans she said, yep, I can make it so it was a little bit stressful for me to create from scratch a little over 2 months but we also will cover a few stops in other countries during our 5 weeks in the EU.

Regarding your trip and for such a large group, it really depends if you wish to organize it yourself from the various USA to Greece or if people living in other parts of the USA will book their own flight tickets and you will all meet in Athens. Depending on complexities, some people decide to seek help of a travel agent or to book through Costco Travel. Also, keep in mind about medical evac/emergency insurance and their requirements if you plan to purchase it. If you are paying with money as opposed to with miles/points for translantic flights I hear/read that it's possible to snag flight deals just around or on Thanksgiving. That's what my friend has told me her husband does for their travel to other European countries (not Greece). If not you don't get flights on special sale, cash prices to the EU start serious fluctuations upwards in March all the way to summer, but this is for my airport that AA has a monopoly on and also Lufthansa flights but their prices are always higher. Maybe prices are better out of airports in NYC, DC, Boston and the like.

Yep, I'd first get translantic tickets first before buying domestic tickets and pay attention at your transit times and I would advice against connection times of say 2 hours unless you wish to be stressed out especially coming to the EU outside of the EU countries.

Thank you @okse26_26. Sounds as though November/Thanksgiving will be a good time to book airfare.

Aside from your flights, what are you thinking about on arrival -- unless you all are just staying in Athens for a week and then going home, you have a HUGE task ahead. Ive done this many times for groups of no more than 5, and I was Boss... aand still, it was like herding cats. Gettng around in Greece is Nothing like traveling in Britain, France or Italy... vets of these are often stumped.

You might consider using a GREECE-based travel agent for accommodations, logistics of getting from place to place and various tours. People who've never used agencies are hesitant, but no upfront commitment for inquiries. They make most of their € from commissions - but that doesn't add to Your cost, because they get lower prices. The reason I say Greece is, US agencies know llittle about Greece and use "cookie-cutter" itineraries, and if something goes awry, they are far away and dont know how to hellp. Athens agencies are up to minute on costs & condition. When there's a "glitch" due to strikes, weather, etc etc they can fix things with a phone call. Two Athens outfits that for decades have good reviews on forums for dealing online with N. American tourists are Dolphin-Hellas and Fantasy travel. They are very busy now, but you might consider emailling such agencies about Sept 1, when they're breathing a sigh of relief, and wrapping up this season.

What we always suggest is be VERY specific -- vague is no help. Tell them length of trip -- desired exact arrival/departure dates if you have them... and latest arrival TIME of anyone. Tell how many, ages, BR requirements (inclluding twins, dbl, queen bed requirements), preferred budget range per BR per night (in Euros); also challenges -- llike mobility, sea-sickness. You can give a "wish llist" of Island & mainland destinations... (but please please look at a map first!! and don't list places widely separated, in different island chains, with nonexistant connections). IF you want specific day-tours at a destination, be specifc. Write both agencies and any others the same letter, ask for an itinerary proposal with an approximate cost (saying u understand it may change due to conditions). Send emails at same time & see who responds fastest, with best proposal. Even if none works for you, it will give you an idea of the challenge ahead. NOTE: Such itineraries often include "transfer" arrangements from ferry port or Bus station to the hotel/villa etc. For a couple, I think that's unnecessary, 2 people can just find a cab. But for eleven -- a different story!

Wonderful advice, Janet! Yes, finding a great travel agent in the country you're going to visit is a much better idea. From your experience, what happens with the travel insurance and evacuation/med. emergency if going with the foreign travel agent and you're a resident of the USA? Is it required or voluntary to buy? Should Americans stack up another insurance for travel dates from the USA?

BTW, I love your comments. I'm new here but I've come across a few your helpful and informational posts intertwined with some humor.

I do not understand your particular worry about travel insurance. That is entirely separate from the work done by a travel agency. When travelilng, I have used, and advised other Americans to use that great online resource, InsureMyTrip dot com. It is NOT an agency itiself ... it's simply an easy to understand service for you to get & compare quotes very readily from a wide variety of insurers and choose what' best. YOu choose what TYPE of insurance you need.

People who do not go on a cruise or buy a complete tour, but who just pay-as-go for hotels, transport, admissions etc, do not buy TRIP Insurance. They should only should get a MEDICAL insurance policy. InsureMyTrip shows an option called "compare quotes." lets you pick out 3 policies and see -- side-by-side -- exactly what amount you'd be covered for each service.

The final good thing, in my opinion, (at least, when checked 2 yrs ago) is this : Yes, you can click & buy online. But if you prefer, you call the phone number, and a nice motherly person (like those nice ladies who used to chat with you on LL Bean) will answer, and go thru the process with you step by step. AND you can ask them to send you a Print-out of the policy. I've been medically insured at least a dozen trips this way, quite affordably. I ve luckily never suffered major injury or illness, but once when I had another prolblem, their trouble-shooting lline helped me. Only thing that would put me off would be IF to save a few $$ they outsourced their phone assistance to an offshore call center with long waits & people working off a script. NOT My thng.

Thank you, @Janet, for your comprehensive response.

We have travelled independently to Greece previously and will again this Fall. We are planning this family trip to celebrate several big family milestones coming in 2026. For the sake of simplicity, we have chartered a weeklong cruise out of Alimos Marina departing on May 23, 2026. The plan is for everyone to arrive to Athens by the 22nd. As hosts, we will cover airfare but family members will book their own flights so they have the flexibility to add on travel before and/or after our time together.

Given that it is not currently possible to book flights or a hotel in Athens for next May, and our recent experience with a flight cancellation 5 months out, I am seeking community wisdom on when to best do so. So far, it seems the recommendation is Thanksgiving-ish.