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Small Sailboat Cruise Options

Hi All!
We are going to Greece for 4-6 weeks starting in mid September. We are thinking about starting the trip with a 1 week sailing cruise so that we can acclimate, see various locations/islands and not have to worry about much trip planning early on. After a lot of research, we are thinking it might be enjoyable to "wing it" and not make hard plans for staying in any location. The cruise may help us decide on a few places we want to visit for a week or two.
What are your thoughts?
We do not like large crowds, so the sailing cruise size we are looking for is no more than say 20-30 people on the boat.
Suggestions? Things to research? Places to look?
Thanks!!
Roger L
Silverdale, WA

Posted by
2287 posts

An 8-day cruise in the Greek islands on a 20 or 25 cabins sailboat costs at least €2000/person in September (closer to €3000). You make stops in the islands but you don't have enough time to visit.

It goes without saying that most of the time these are very touristy islands.

Posted by
16 posts

Ouch, yep that is more than we want to spend and we definitely don't want to "cruise" to the major tourist islands... guess this thought is likely not going to work... any other ideas on my request?

Posted by
16 posts

Yes, and it was those replies on that prior thread that made me rethink how we will experience Greece the first time. Hence, consider a small 1 week cruise the first week that maybe hops around some islands and THEN decide where to spend 1-2 weeks in different locations. But it also looks like there aren't any good options for the cruise first...

Posted by
2287 posts

Since your original intention was to stay on one island and take day trips to neighboring islands, which is rarely possible, you could do like two couples, an American and an Australian that we met a few years ago in Paros. They stayed for 12 or 13 days (I don't remember exactly) in the same accommodation as us, in Paros.

They left twice for other islands for 2 or 3 days, taking just a small piece of luggage and keeping their studio in Paros.

Of course this involves paying for 2 accommodations and only using one.

Paros is centrally located enough to do this kind of multi-day trip.