I spent 12 years in Europe (until 3 years ago), with annual trips home by air. I didn't have any problems.
You will find it very difficult to obey every detail of the immigration laws, and will be very constrained in your travel if you do.
OTOH if you completely ignore the laws there is a good chance you will get caught, and possibly fined and deported.
The answer is to learn where the enforcement is a problem, and where it isn't, and where there are legal options. The situation is changing, and becoming more difficult both due to stricter enforcement and more nations joining the EU. But there is still room to maneuver, and the best way to learn is to ask those currently in the marinas
in the Med for their experiences.
My information is dated, but possibly useful. In addition to the African and Mid-Eastern states, ex-Yugoslavia (save Slovenia), and Turkey
, there is always Gibraltar
. That provides plenty of interesting and legal places to winter. I wintered in Italy
3 winters with no problem; I was asked once by the CG but they shrugged it off. On another occasion a kiwi was silly enough to go to immigration after overstaying and asked for a residency permit
; that brought some unwanted attention but in the end nothing happened (other than a distinct loss in popularity for him in the marina). I spent 4 years in Turkey
, with a day trip to Greece
every three months to renew the visa (and buy cheaper alcohol). I also spent a winter in Gibraltar
. So I don't see any problem with wintering as long as a little research
is done. In practice the biggest problem for wintering is Greece
but even that is possible.
Sailing through the Mediterranean
EU in the summer shouldn't be a problem either, particularly if a trip to Croatia/Montenegro is included. The major concern there is Greece (again), which has been very strict for a very long time: they like their fines. So if eastbound be certain to have the passports stamped when returning to the EU and then check out of Greece within 90 days without fail. Missing the Dalmatian Coast would be a crime anyway. And Turkey is a real treat so don't be reluctant to move along.