Just to give you how we worked it. We arrived Horta and had some boat work to do which took a couple of weeks. Then over to Terceria where we spent way to much time but it was St John festival and what a great week. Then another island stop for a couple of days and to wait a weather
window to Lagos, Port. At the suggestion of the Azores customs
we checked out to save the sailing days. When we checked in in Port we were informed we had XX days left in Schengen. Portugal
counts days as seems a bit strict about it. We traveled through Portugal
for about a week then moved on to La Linea Spain
near Gib as the Gib marinas
are outside Schengen and were expensive and full. We traveled for about a week in Spain
and actually went to Madrid to see if we could get an expended visa for the winter. This was at the National Police. They told us our best bet was to take a train to Lisbon, go to their embassy and apply there and get it and then come back. Or as they put it just stay we don't care.
Our problem was we were going to fly back to the USA during the winter and would have been over by a lot and we had been warned that some airport customs
folks take their job serious and our massive overstay could cause a fine and potential red stamp. A 1% chance of that was to much to consider so sailed 1/2 up the Spanish coast stopping along the way and then over to the Balearic Islands for a while then down to Sardinia where we checked out and had spent over 100 days in Schengen. We have a habit to trying to use small out of the way ports
to check in and out to get away for officialdom. The only concern for the customs guys was when they asked our next destination
and told them Tunisia
and they said non Schengen, smiled and stamped us out.
We spent the winter in Tunisia
. Our next summer we sailed to Sardinia and got a booklet that we were told we had to have stamped at each Italian port. At our second port went to CG to get it stamped and they said no stamp needed but I wanted on it was 35euro which I declined and never tried again. We sailed to Corsica
then over to Rome down the coast with stops along the way thru the Messina Straits, across the boot to Ortanto and checked out there. We had about 20 days left. We went to Albania and land traveled to Macedonia, Kosovo and sailed up to Montenegro where we land traveled to Serbia. All that time we were getting stamps in our passport and we had trouble trying to find our Schengen days. We sailed up through Croatia
and crossed over to Venice and checked back in and the customs guy told us we now had 90 in Schengen. We knew better as it is 90 in 180. NOW I can give you a case that if I worked at it a bit I could move the calendar around so the time getting to Albania applied to the 180 with Tunisia but that might be a strectch.
We sailed down the coast of Italy
and had to wait our a terrific blow. We thought about checking out there but Malta
is ex Brit and they have a way to sometimes to cross every "t" and dot every "I" so we decided to check out in a small Italian port of Lambadusa and they took one look at our passports and could not figure out where we had been when. They even took them to a back room and came back smiling with them stamped. We spent the 2nd winter in Tunisia.
This past year we wanted to sail the Greek islands
so we sailed to Sicily
and got the book again. At a stop in Sicily
we went to get the book stamped and they took it from us and told us not necessary. We went on to the Aeolia Islands and then did a couple of overnight to Brindisi to see friends where we checked out and on checking out they asked for our book and we told them we it was taken is Sicily and they said you are not suppose to be here just leave and leave now. We and sailed over to Albania and down the Albanian coast and checked back in in Corfu. We got the dreaded log and most places we got it stamped but not all. When we were asked about it when we had to get it stamped we just said we anchored out. We went across Greece
and checked out at Samos and spent just a bit over 90 days. No issues. We are wintering over in Turkey
where you can get residence which we have.
To us it is a game
. First we do not use big harbors to check out. Second we do a lot of inland travel in non Schengen countries with lots of stamps in our passports so we can't even tell where we have been and when. Third we never fly out of a Schengen airport
for our 1st flight. We had a couple of people tell us that in Frankfort(?) they check Schengen even on folks coming from outside Schengen and changing planes. They did not do that to us.
Third we like to check in and out of countries who have a lot more problems than a couple of old Americans on a sailboat and almost all are just glad you are there. Greece
you just have to make a judgment call as some are stickers for officialdom and some are not. If they look like they are just try the next island.
That is how we did it and it works for us.
And the Med us huge as we have yet to be to northern Italy
(west side) any of Turkey
, or Morocco
of the Black Sea and we still have a few Greek Islands