How is travel in Greece without making reservations for accommodations?

Where in Greece do you plan to go ... the mainland or the islands? And how fussy are you abut the places you stay?

We've done a bit of island-hopping at that time of year without reservations. Some of the larger islands may still have people meeting the ferries. Or you could probably wander around and find a hotel. But we always call ahead (or use booking.com) the night before we leave our current island, and book a place on the next one.

If you're talking about the mainland, I would guess you would be OK but someone more experienced will have to chime in on that.

I used to do that often in May, and Sept-Oct is much the same, and it's not at all "risky", there will be loads of lodgings, and at good "walk-up" room rates. That said, you can have flexibility PLUS the best experience, if you do some "homework" in guide books on the best general locations in a particular island. Not just websites, which can be promotional; guide books can be more candid. Work up a list of 4 or 5 promising places in the area you choose. That way, when you step off a ferry, you won't be limited to the people waving signs & room photos at you. In some islands you'll get a nice room that way but it may be way out in the boonies, not near a beach or near a bus. Also in Sept-Oct, in some islands that don't have larger permanent populations, the farther-out locations can be in "closing-down" mode, with many hotels & pensions, restaurants putting up shutters.

With a big of research, that's a great way to travel ... you can be impromptu and say, I love this place lets stay longer or equally, Lets move on, I'm ready for something new.

I well remember on my first trip, in 99, watching the ferry ramp slam down in Paros, at 2:30 in the morning, with no reservation, thinking, I'm a grandmother, what am I doing, am I nuts?? But it all worked out wonderfully, and every day was a discovery ... and it still is!

I had no trouble with just showing up in early October on some pretty small islands (Agathonisi, Lipsi, and Patmos in the Dodecanese). In the second half of October, some places I stayed may have closed, especially if the ferry schedule was further reduced. On an earlier trip, I also did this in April.

We rarely had reservations at that time of year, the exception being a place in Matala, Crete that we planned on a week and the time period was fixed. Other than that, we did look through Lonely Planet, Lets Go, and other guides and had a short list of places at each stop that would work. We would then either call ahead the day before or just show up. At more than one stop we did just bargain for a room at the docks. In the end, always found a room with little effort or delay, all were very acceptable rooms and we had a great time. We did change plans as we went, spending more time at a place or two, and there was at least one instance where the ferries did not run due to winds/rough water, so the strategy paid off.

We didn't always get our top choice so had to settle for less comfort and/or convenience at a higher price. But we always found something acceptable if not the best we could have done reserving (and locking in) ahead. Its a trade-off.

Go for it; not risky that time of year. As you learn the ropes you will find it easier at each stop to find nice lodging.

However, if you're running into problems (carrying your luggage from place to place with little success), you can always jump online and start booking. As a school teacher who does all his travel in the busy summer months, I would love to do a trip that did not require complete planning, but without that luxury we do very well planning ahead and booking ahead. Using booking.com or airbnb, we've had nothing other than spectacular accommodations in Greece.

Thanks for all your advice. I would like to island hop via ferries?plane
and definitely want to go to Santorini and Naxos. Since Santorini is so popular, I might book a couple of nights there in advance. It is good to know that we can get good accommodations without pre-booking everything.

I doubt you will have any issues in Naxos.. and the rooms are so cheap.. we got a room for 45 euros.. will be there in 2 weeks.. let you know how it is.. ( it has good reviews.. ac, close to beach and town, and includes breakfast!!!)