Winter is shitty in Greece. Its very rainy and can get cold. Many smaller coastal towns or islands are ghost towns. Not much to see for the
family. you will have a hard time getting to other locations from there as many airports are either shut down or operate just very few connections in
winter. Most connections to Greece run from where where the tourists live (uk,
germany,
netherlands, etc) but very few to other holiday destinatinons. So its hard to get from Greece to the Balearics for example.
If you just want to shop around it may be more feasible to base yourself somewhere where you can fly easily and cheaply to the different locations in the
Med.
The UK for example is a few hours away from the
Med but has lots of
budget airlines like Ryanair or Easyjet. Cheaper to fly from London to Greece than some national flight within greece. I'd prefer that over greece anytime.
Or plan for something like a week in
france, a week in
spain, a week in greece, etc.
Greece has many ex-charter
boats and quite a few owner
boats there have been sitting unused in the yards for years. Same is true for
croatia as far as I have seen.
I have seen more owner boats
for sale in
Spain and especially
France.
Owner boats in most european countries must have VAT paid status to be used by the owner if he is EU citizens. So many true owner boats have VAT paid status. Theoretically this adds another 18-25% to the
price for you, but in reality its much less.
In the deep south like greece and
italy folks are very creative to get around this, like registering on a US company and such. But in many cases its still illegal, even if authorities are blind or corrupt.
If you want to sell in the Med after your trip you may see that selling to private buyers is easier if your
boat has VAT paid status. So the amount of VAT is not necessarily
lost and a
boat with VAT paid status will make life easier for you (no temporary importation, no problem at
customs visits, etc).