I have been working as a charter skipper
for long enough to be able to answer some of your questions.
First of all Greece
is the best place to charter
- say all clients I have had who have also chartered in other countries. Better than the Carribean at least. The reasons are the islands (unique) the friendliness of the Greek people, the weather
and the sea that is practically free from nasty reefs
, tides, etc. Navigation
If you have sailed extensively you might find a flotilla a bit limiting. Flotillas are popular with families and people feeling uncomfortable on their own. They end up as a small expatriate community afloat.
Communication is no problem as most Greeks understand and speak some English. In fact they are happy to have an opportunity to practice.
France and Italy
is not the place to be unless you can speak French and Italian respectively. The French simply refuse to speak anything other than French and Italians find English very difficult.
Best month to go is any time from April to October. At the extremes of this time you may get some cloud and even some rain but mostly it is bright and sunny. July August may be too hot for some people staying on land but on a yacht there is almost always some refreshing breeze.
The risk is sun burn if you expose yourself too much too soon.
What was said about too much wind in July/August is true of the central Aegean (Cyclades). There are also some less windy areas like the Ionian
islands, the Sporades and of course the Saronic gulf.
To give you an idea, when you have force 4 or 5 in the Saronic it may be 6 or 7 in the Cyclades
. Even then with some local knowledge you can plan a course that will make it comfortable. I do this the whole time with my clients.
Charter companies are very much on a uniformly good business-like level. I have worked with most of them. They all have devoted clients and they all have some dissatisfied clients.
I also have a charter yacht which may be available for your time frame but I only charter her with myself as a skipper
because I have suffered damage from self sail clients for about 10 years. If you came along you would be free to sail her yourself but I need to be there to make sure there are no problems.