Greek Isles in September

It's completely realistic. No reservations needed. There will be room-finder businesses close to the island ferry docks. Locals will meet the ferries with offers for rooms to rent. Ferries won't be full.

Thank you!

We always book accommodations in advance but you could just hop ferries and find something at each island to stay at.

You will be traveling during the start of the off-season but there still will be regular ferries to most of the islands. Some of the smaller and out-of-the-way islands may have reduced schedules. You should have no problem getting ferry tickets or lodging as there will be plenty of available places that time of year. We go to Greece in October and never had any problems with ferries or getting a room! You'll love Greece that time of year, cheaper accommodations, less tourists and still very nice weather!

I agree that you'll be able to find whatever you want as a "walk-up" in September ... and for that reason, and because you have the time, I suggest you do a tiny bit of homework. No need to buy a book (this concept is foreign to many people under 40 anyway, LOL), just stop at local library. Check out a couple of guides like ROUGH GUIDE to Greece, or GREEK ISLAND-HOPPING, or even LONELY PLANET. Just look at the half-dozen islands you're most interested in, and check the maps of the port towns & nearby beaches ... it will give you an idea of the most convenient locations. Jot down the names of 4-5 lodgings, and photocopy any maps that seem handy. That way, if you step off the boat and there are a bunch of people waving photographs at you, you won't fall for a good-looking photograph of a balcony --- and then find out the lodging is waaaay off in the boonies, not near a beach OR a bus.

If you do enter into negotiations with a dock sign-waver, make them show you the location of their place, on your map. If none of them are in the area you want, then just set off to that area, with your little list in hand, and do walk-ups.

On my first trip to the islands, also off-season, I learned from experience. On Naxos, I took a suggestion, and fond that the hotel was way up at "top of the town"... reached by walking up a stair-step path with a heavy bag! It had a lovely view, and I don't regret the adventure ... but it was a loooong walk to the beach area, where i've now learned to stay. Just an example. Homework helps you be flexible, and still get the best experience.

The flexible plan is the way I have traveled in Greece in spring or in October, I'd I would plan to do the same in September.

As Lee mentioned, you shouldn't have any trouble finding a room as anyone with rooms to rent will be waiting at the docks for new arrivals (these ones were in Naxos).

Thanks, everyone, that is very helpful and I feel a lot better about going without reservations.

We are more comfortable knowing a little about our lodging. So when we island hop, on the day before we leave an island, we book our hotel on the next one. I bring a guidebook or a list of possible hotels, and just use Skype to call them.