I’ve just noticed, do you mean September 2026? If so, I’m surprised hotels are booking so far in advance. We’ve never booked that early and hope it doesn’t become necessary.

I’m heading to Italy next year and had planned to make some hotel bookings a few months before.

Hi dreamon....yes this is for next year and Hotel Grotta took my reservation. I don't know how many rooms some of the places we're interested in have but we travel to a hotel in Rome about every other year and we've had trouble getting rooms if we don't book far out, that is, if it is anywhere between say April and September. I am one of those crazy people that likes to secure my reservations, so I don't miss out on where I want to stay.

Hotel Grotta is a great pick, close to town but easy to reach the beaches. Adding Sifnos is worth it if you want something quieter. Early September should be warm but not crazy busy. That Zakynthos write-up by Kay is Murmuring nails the Greek island vibe: beautiful, calm, not overdone.

We are staying at Iliada Suites which is next door to Hotel Grotta. I would have like to have stayed there but we prefer larger rooms and they didn't have any that suited us.

We booked Iliada Suites almost twelve months ago, and are finally going in three weeks.

We almost always book our hotels ten to twelve months in advance, as we like boutique style hotels and generally have specific room requirements. Those rooms go very fast.

I've stayed in both Grotta and Iliada.... in the latter, we had best of both worlds... the first time, Grotta unexpectedly was full after we'd reserved, so they put us "next door" at Iliada, but we had breakfast at Grotta. We had the front apt had ililada, with lovely terrace out front, gorgeous sunsets, we often picked up dinner-to-go and sat there on terrace. However, we were in MAY and it was lovely. When I took friends to Grotta in September, the "Meltemi winds" were SO Strong, one could not sit outdoors at all!. I appreciate that you lilke to b ook far in advance -- but then you also should research the weather. in Sept - O ctober I would definitely book at Naxos' Ag Giorgios (St George beach), which is Below the town to the west ... where the water is still choppy but one is sheltered from the wind. Good luck, and take jackets for the evening!

The area around Grotta can get very windy

Both Sifnos and Naxos are great choices. I’d suggest starting in Sifnos for the quieter feel, then finishing in Naxos where you’ll have more ferry/flight options back to Athens. A car is handy on both, but not essential if you’re happy sticking to main towns and beaches. September is a perfect time with warm seas, pleasant weather, and fewer crowds.

TravelerJan

Thanks for your reply.

I have had a few friends stay at Hotel Grotta, all in September and October, and none of them mentioned the wind, hence why I wasn't concerned. In fact this is the first time I have heard it mentioned.

From my research the winds are far worse in July and August, but of course I haven't been so I could be completely wrong.

Since we are leaving in a fortnight, I would never cancel now and let them down. We have a large suite with a big indoor area, also with views, plus a jacuzzi, so if necessary we can put up with the winds and watch from inside. Fingers crossed that it works out.

Does anyone have any preference in terms of the website to use to book ferries? We need Naxos to Sifnos and Sifnos back to Athens. Thank you.

Can you book directly with the ferry company? Always preferable to my mind, no dealing with a third party in case of problems.

I agree with KayF. I would also check my options on rome2rio.com

Ferry company for the endless (100 USD/pax) catamaran ride from Naxos to Sifnos: https://www.seajets.com/
For Sfnos - Piraeus you may also check https://fastferries.com.gr/en/ (45 USD/pax)

MIK/MlF, you have "piggybacked" on a very old discussion thread, so we don't know what your travel dates are. However there are only a couple of Weeks or weekends in the Entire year when I would consider ordering tickets ahead. It isn't like airlines, nothing like it.

When are you traveling? except for the week before/after August 15 (huge greek holiday), it's always better just to buy at a local ticket agency a day or 2 beforehand. The Blue Star ferries in the cyclades have up to 1800 passengers (!). And even the smaller Fast-ferries have over 500 passengers... the preferable larger fast-ferries, which also carry vehicles. have 1000-1200 seats. IF your desired ship is a smaller once from Naxos, just go to local agency on waterfront on day you arrive, rather than waiting til day before departure. Then, if there are any delays or cancellations due to weather, it's SO simple to get a refund or to reschedule. I"ve traveled to/from islands on 13 Greece visits, and have never booked ahead online. I realize this is a habit, from air travel, but please resist.

Travelerjan, she has not piggybacked. This is her thread for a trip this September (even though she started it last year).

Ah, then catching up. My advice is right, for September certainly!