Greece Itinerary Questions / Advice
 

Is this plan too ambitious for a late summer holiday?

Flying into Athens (at night), flying out of Santorini (in the evening). In total 10 nights to play with.

Currently my plan looks like the following: 2 nights in Athens, then catch the early train towards Meteora with a 1 night stay in Kalambaka. The following day, leave by evening train and stay in Athens. From there, morning ferry to Naxos for 3 nights, and then ferry to Santorini for 3 nights.

I feel like it gives a great mix of everything - city, mountains, islands & beaches, but I'm wondering if it's doing a bit too much.

Also, if anyone has recommendations on where to stay in Naxos, that would be much appreciated!

If you want recommendations on good places to stay during THE HEIGHT Of High Season... you would have needed to start a lot earlier. All the best places most of us would recommend are doubtless booked solid for Aug 1 - 20 -- and it's a waste of our time & yours to describe things that aren't possible. Best to just get on booking. com and look... being SURE to click "LOok on map" so you can see where a place really is. Sometimes places will hint that they are on he beach when they are not. Also, if they are located far from the bus routes, you are forced to rent a car.

I'm going near the end of August. Most of the places I've found that I want have accommodations available. My main focus was on if I'm doing too much trying to go further inland and then back out to the islands, hoping this would catch the eye of someone who had done a similar route or considered something similar. Long shot perhaps, but you never know.

Re: waste of time - I've done plenty of my own research. There is no need for you to be patronizing, I'm not banging your door down asking for help. Merely looking for tidbits that may be value added.

End of August is much better than earlier in the month re accommodation, as you have already discovered. That’s my favourite time for the Greek Islands. Your plan looks feasible, but I have no idea about train travel to and from Meteora.

Were it me I would do it the other way round, flying to Santorini first thing in the morning if you arrive in Athens too late for an evening flight. Take a ferry from Santorini to Naxos, then back to Athens by ferry or flight, followed by your train trip to Meteora. That gets you back on the mainland early in the trip, avoiding the possibility of being stuck on an island due to weather or strike.

Thanks, that's an interesting point. How often does a weather delay that time of year or strike happen? Is it simply one of those chalk it up to bad luck / timing things?

A ferry strike actually did happen, when we were on Santorini and needed to return to Athens via ferry, to catch our flight the next day. This was in September 2016.
We were lucky, because our concierge had advised us in advance about the upcoming strike, so we bought a flight instead.
Good thing, as many people were stuck on Santorini and missed their flights.

Despite that, we LOVED Santorini.

You would be more likely to encounter strikes in September than August, when many Greeks are still on holiday. July and August are the months when the Meltemi (northerly winds) are strongest, but you are unlikely to encounter a Medicane (Mediterranean hurricane) as happened in September 2020. Perhaps I am being overly cautious, but if there is no reason otherwise, islands first and mainland second is what I would do.

Your plan sounds feasible to me but you do have three stays in Athens (assuming you stay in Athens the night before flying home). Travel in Greece tends to make that happen, in my experience, but shifting hotels frequently isn't ideal. I agree with others about visiting the mainland second, from the point of view of being stranded (not likely but possible). You may also be able to travel from the islands to Meteora in one day, avoiding an extra stop in Athens (although that wouldn't be the end of the world).

Thanks all - a few things to clarify:

I've learned that I prefer the adventure leg of the trip up front, with total relaxation on the back end. Hence, Santorini last, and flying out of Santorini instead of returning to Athens to save time. Two one ways ended up being cheaper than the round trip, which made it even easier to go this route. This gives me 2 stays in Athens: upon arrival, and returning from Meteora. It seems like the trip to Meteora takes around 4 hours each way via train, so perhaps it would be better if I could spend more time there as opposed to one night.

Finally, it leaves me with 2 ferries to take: Athens to Naxos, Naxos to Santorini. The concerns mentioned are good to note, and leads me to consider skipping Naxos, taking more time to explore mainland, and then fly into Santorini instead.

Don't forget to check on the schedule of the monasteries. They are closed on different days of the week and you may want to see certain ones.

Yes, saw those - will be able to see all that are open! Thank you.

I think approaching Santorini on a ferry is pretty special and you get a perspective of the island that you don't get from being on the cliff tops. Taking ferries is part of the quintessential experience of travelling in Greece.

i am in Greece now. When we were in Rhodes ferries went nowhere for several days due to high winds. Happens alot. So good advice to be back on the mainland prior to your flight home.

If you visit Santorini first, can you fly to Santorini from where you live on one ticket? That is what we did, and it went very smoothly. We flew Boston/Zurich/Santorini, all on one ticket. So you don't have to fly to Athens on one ticket, and then get a separate ticket to Santorini. If you miss your flight to Santorini, the airlines are not responsible for re-booking you because it is a separate ticket.