Cyclades Itinerary Advice - Sifnos, Naxos, Santorini

Based on multiple visits to both islands, I'd just say, reverse the 2 ... 4 on Sifnos, 5 on Naxos. Both lovely, Naxos has SO much to do/see .

Thanks!

Based on probably even more visits than #1 I'd stay with your original plan. I've even stayed for up to 3 weeks at a time on both.

No amount of time is a given. What it really comes down to is what you want to do with your time, something that #1 doesn't even mention. For example, the villages on Sifnos are more attractive, more typically 'cycladic'. Sifnos also has the better hiking possibilities, if one is interested in hiking. Sifnos also will be less busy and with more of a small island feel. I've always enjoyed Naxos mainly for the bustle of the main port town, and I've always stayed in the old Venetian quarter for that reason. To each his/her own ..

Although bottom line for me is that even 5 days isn't much for either, I wouldn't quibble over a day, one way or the other.

The connection at Ios is extremely tight. Be careful!

What you have is OK. I would not fuss about number of days on Sifnos/Naxos. I have stayed on Sifnos and Naxos many times before, going back through 30 years.

The connection on Ios is far too tight, I auto-add an hour or two to a ferry arrival time. It happens most of time, you have to be realistic.

Assuming the same Hellenic Highspeed ferry from Sifnos you would have a better chance by going to Santorini rather than Ios. That would give you a 3 hour buffer for the 15:30 Bluestar Santorini to Naxos. That is also a cheaper ferry to balance the cost a bit.

I presume your flight from Santorini is an international one ?. If not, do Santorini before Naxos.

Thanks everyone. Regarding the Sifnos - Ios - Naxos ferry, we had been thinking that we would arrive in Ios at 11:40 and take a 14:16 that arrives at 17:30. Assuming, meckerdv, that you thought we would hop on the 11:30? We were not planning on that, however, it sounds like at least 2 hours buffer on ferry arrival makes sense.

Since we do need to fly out of Santorini, we will still do Sifnos - Naxos - Santorini but it may make sense to ferry thru Santorini from Sifnos to Naxos, rather than thru Ios.

Thoughts?

Thanks everyone.

One additional question: what is the best site to buy ferry tickets from? I was looking at directferries.com but would you suggest another?

We have obviously not the same timetables. I get for Friday June 2nd:
either Sifnos dp 9.55 - Ios ar 11.05 (Hellenic Seaways, non stop) or Sifnos dp 9.20 - Ios ar 11.40 (Sea jet2, with intermediate stops at Milos and Folegandros);
Ios dp 11.30 - Naxos ar 12.15 (Champion Jet2, direct).
According to the Bluestar timetable, Bluestar2 will NOT call at Ios on Friday June 2nd:
"(1) The vessel will not call at IOS from 07/04/17-19/04/17 and from 01/06/17-03/06/17"
http://www.bluestarferries.com/en/travel-with-us/domestic-lines/timetables/piraeus-syros-paros-naxos-ios-santorini-anafi.html?destination=&anchor=content-category

But you can get the Bluestar2 at Santorini, of course (with both above mentioned catamarans)!

Thanks, this is really helpful - I was looking on directferries.com and didn't see the blackout for those dates.

Do you prefer to book directly with the ferry companies?