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Cyclades in September - Plan it or Wing it ?

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Cyclades in September - Plan it or Wing it ?

I'm slowly putting some kind of a plan together for next September with the help of all the knowledgeable folk on here.

We will fly to Santorini on 4th September next year - have 17 days/16 nights and will fly back from Mykonos.

We would love to have the confidence to just wing it - maybe prebook our first couple of nights in Santorini then just look at the ferry boards for sailings to wherever and go to which island takes our fancy at the time.

So my question is - is this feasible in September - will there be rooms on each island readily available at short notice? Are there any potential pitfalls that I should be aware of ?



Edited: 12 October 2012, 12:09
Warsaw, Poland
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1. Re: Cyclades in September - Plan it or Wing it ?

Wing it of course. I do not expect major problems with accommodation. I would book Santorini because although there will be no shortage of rooms in Santorini I'm not sure if you will be able to find any hotel owners touting their rooms at the airport. Most of them are to be found at the seaport.

I would also be wary of two things:

1/ If you plan to go to Anafi, I would advise to book too as apparently Anafi is getting increasingly popular, ferries are not daily and there is a risk of it being packed in the beginning of September. You may face a night or two on the beach as a result.

2/ Not all islands in the Cyclades are easily connected with Mykonos, especially towards mid and end of September. The ones south of Mykonos are only linked to it by small high speed catamarans that are not as reliable as conventional car ferries. If you are not planning to spend a couple of days on Mykonos before your flight home, when 2013 schedules are out give some consideration to which island to put before Mykonos.

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2. Re: Cyclades in September - Plan it or Wing it ?

I agree with Ozzlem: wing it. However, I wouldn't expect Anafi to be full in September. Also, you will find catamarans from Paros or Naxos to Mykonos on most days in September, so it won't be that difficult unless you are trying to get there from somewhere like Folegandros or Sifnos.

Birmingham, United...
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3. Re: Cyclades in September - Plan it or Wing it ?


The last time going to the Cyclades (33 days) I did the reverse - arrived Mykonos, left from Santorini.

I booked 1 night on Mykonos, and 2 on Santorini. The rest was just winging it with a very rough outline route.

I would suggest get going straight away to your first island, delay it by a couple of days means you have less flexibility for the rest where those days may be needed. The latter is not so necessary if you are just doing the tourist axis of the central Cyclades islands, but helps if doing islands with not so frequent ferry connections.

The reason for booking Mykonos is that looking for a decent room on arrival is always time consuming there, relatively long hi-season, and to a lesser extent Santorini.

The snags of doing this are more for the first timer who is unfamiliar with a particular island. e.g. on some islands I won't deal with quayside room offers at all, but other islands I use them. On some islands there is no one offering rooms so you just look around. Obviously if you have been there before you know what streets/area to wander.

Local island travel agencies deal with ferry tickets and also accommodation if you are stuck for somewhere.

There are no particular snags other than the time it takes looking at rooms. That can vary from 5 mins to maybe an hour or two.

The exceptions are the 2 islands mentioned. The big advantage is flexibility to enable you to get to the least touristy islands.

Nanaimo, Canada
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4. Re: Cyclades in September - Plan it or Wing it ?

I can understand your dilemma! We just had our first trip to Greece, and we prebooked everything! If we were to do it again in September, I would be more comfortable with "winging" it.

In Naxos, we were the only ones at our hotel for the four nights. In Paros, the hotel was FULL! But we would have had other options in September if we hadn't prebooked that hotel. It was also much quieter after the bike group left!

Every port had people with their signs to advertise their hotel/studio rooms. And they give you a ride to the place too. Just make sure you look at their binders. They show you pictures, and they should have a map too, and then you can see how far from a beach it is, or anything else.

I would want to book Santorini though. It just feels good to get off the plane and know where you are going! Flights can be delayed too, so that is another good reason to at least have a bed for the first night.

Winchelsea, United...
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5. Re: Cyclades in September - Plan it or Wing it ?

Hi Julie,

We did this for our honeymoon 2 years ago, in late September and winged it - apart from the 3 nights at Old Oia Houses in Santorini - we didn't want to risk them not being available !

I'd definitely recommend it - it's much easier to check room quality and negotiate prices with a real person rather than a search engine for one thing.

We stayed in Eleni's rooms (Paros) and Despina's Rooms (Naxos Town) and paid a paltry 35 euros a night. I'd recommend both as good places to start your search.

Have fun. And go hand luggage only ! It can be done (even on honeymoon)...


6. Re: Cyclades in September - Plan it or Wing it ?

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