Brilliant idea - go for it!
To deal with your questions one by one:
1. A 31 footer is not too small BUT you need to be realistic about weather
conditions if you want to enjoy yourselves. Also you mustn't be too ambitious in passage
planning as you won't average much more than 5.0 knots in the Med.
2. I wouldn't bother with air conditioning, but a bimini
(rather than just an awning) is a real asset. Equally you'd be better off with a decent solar
panel array than a generator
unless you're absolutely set on having ice for your daily G&T. We have both and our generator gets hardly any use in a typical season. However, you'll need a powered windlass
for stern-to Med mooring
, which you'll be doing a lot of if you get as far as Greece
, and a passarelle (or at least a plank) for getting ashore.
3. Can't comment as I have no experience of this.
4. Your budget sounds OK as long as you don't plan on spending most of your time in marinas
(which can knock you back €75 -100 a night in some parts
of France and Italy).
5. Your planned itinerary is much too ambitious. You'll spend all your time sailing and won't get much time to enjoy the history
and culture of the places you visit. For a six month itinerary, I'd go no further than S. France (including the Iles d'Hyeres and the Calanques of Marseille); Corsica
; Sardinia; maybe some of the Italian islands; Sicily
and finally maybe a quick circuit across the Ionian
to the Greek Ionian
islands (though even that might be pushing it a bit). An alternative would be to return along the Italian mainland coast after visiting Sicily
6. What would I have done differently? Well, skipped the S coast of Spain
(which is mostly dire and expensive) and - certainly during the peak sailing season - the Balearics, which are mayhem in July and August.
Hope this helps. The most important point I'd make is to remember that sailing is simply a mode of transport (albeit a very enjoyable one). If you don't allow enough time at your various destinations you might just as well stay at home and race
around the buoys.