Hi - we're currently at
anchor in Portoferraio for free and have spent time in
Spain,
Portugal,
Italy and France in last four years. Can't therefore compare with
Greece or Turkey but we would say €50 a night for a 39'
boat is expensive in May - even here in western Italy!! At the moment the darsena here would charge you €40 plus
water and elec and that's a highish end in costs. Come late June to 15 September prices will rocket here though - we were caught by v adverse winds in Isola Capraia last year and paid about €55 for our 40' per night (including services).
In southern France, here in the Tuscan Islands and
parts of eastern
spain, including the Balearics there are many many
anchorages, which are crowded but perfectly usable. (A chum can come in handy, and some
anchorages are very deep.) In some places you must watch out for the mistral.
Anchoring is free but provision well in somewhere 'ordinary' before reaching the islands as food here (especially fresh veg, on smaller islands) is scandalously dear.
Agree with much of the previous
advice about avoiding the tourist traps etc and
buying food where locals shop - but you must know all that with the miles you've done.
Italy feels dear to us right now but our base currency is sterling so everywhere is feeling expensive. OTOH, we have been prepared to spend
money on seeing the astonishing
history and culture here - such as visiting the Vatican museums in Rome.
If you can watch the
weather, be prepared to move niftily if your anchorage looks like becoming untenable and shop with a bit of common sense, you can live very cheaply.
But, and this is a big one, think v carefully about where and how you want to spend for the
winter. Are you likely to want to be in a marina, or will you
anchor? Do you want to be near a bigger cruising community? Will you be aboard or do you want to
haul out? There is an enormous variety of costs and quality for your wintering options, and you might end up deciding your
route after you've made that decision.