Hi
I had sailed the Aegean for seven years before going to the Ionian. I am saying this so you can understand that I am somewhat familiar with the area.
Santorini has NO good ports and most moorings are untennable if the sea gets rough. I had no idea that there are charter companies out of Santorini. Being a somewhat remote island-look at the map- it makes for a long trip back, if you must return the boat there. May I suggest that you charter out of Athens? Glyfada actually, by the sea. Cavos-Moorings is a good, reliable company and so is Vernikos Yachts. Now payng ahead of time is the usual and customary thing to do, but make sure you know who you are dealing with.
September is a good month assuming the Meltemi - a vicious northeasterly- has died down. Please feel free to write to me at
sokinrev13@yahoo.com should you need further info. I am heading there in May and shoild be around some of September as well. Elias
PS Many of my friends have their dogs in their sailboats. If the dog has been broken-in and is familiar with sea travelling, you should have no problems, naysayers not withstanding.