So, long-term RTW - "Schengen Shuffle" ?
EDIT: Oh holy crap, I've realized how stupid I am... I pulled up a bigger map, and realized I am missing a LOT of space in between... ok, well I HAVE always wanted to visit much of that region of the world (Turkey, Iran, etc???)... still, advice?
So, I knew I had 4 days left on my visa, so I took a very long train ride from Santiago de Compostella to Italy, and from there a train to Zaagreb, where I started my very valuable and memorable Eastern European leg. I even took a day to see venice, sleeping at Camping Alba for the night. A very pleasant night it was, a pleasant day in Venice. It's all good and different in Eastern Europe.
If you got ambitious, you could see Romania, Bosnia Herznogoviaa, a little Croatia, Serbia(Though I boycotted it for political reasons) Slovenia(Which I shoulde have seen, but didn't) then to Bulgaria where you could re-enter Greece if you spent three months in these areas, or hey, even go from Bulgaria into Turkey, which has some amazing nd different things to see. The world is yours, my friend. I hope you take advantage of it.
But that's kind of a dream trip for me, and it would probably take six to nine months, and require a fair bit of time spent sorting out the visa complexities of central Asia. It would certainly be an adventure...given starting in January, you'd probably spend most of the winter at the relatively predictable European end, but there might still be a lot of snow and road closures by the time you get to Georgia, which is where infrastructure starts to get questionable.
If you're more interested in just burning out 3 months of non-Schengen time and then going back, just head as far as Turkey, tour around a bit, then head back. That end of the trip is pretty straightforward, and Turkey is fantastic. My month there was not nearly enough.
Iran's an interesting option, but depending on what passport you have, it may be difficult-to-impossible to get permission to visit. Also, I believe there's an election this year, and the last election came remarkably close to civil war, so I'm not sure it'd top my list at the moment.
I second the recommendations for Turkey too, and might add Egypt. It's not a long flight from there or Europe and the historical sites are amazing.
The other option is to just wait a bit and see how flight tickets look a few weeks before your time in the Schengen area runs out. I mean if you're on an open-ended trip, why not? For example I got a rather cheap deal down to South Africa on Air France a few years ago (from which you could work your way up all the way to Egypt if you were seriously keen), and last year when I was in Nairobi it turned out you could fly in just a few days to Hong Kong for $500... and South Africa was WAY more than that.
So hey my point is don't rule out anything just yet I guess, the lovely thing about open-ended travel is not having to plans months in advance.
Don't take this as gospel, because it's not the way the Schengen rule works de jure. At the same time, my experience and that of many others is thus: the three-month Schengen rule resets once you leave the zone. I'm sure that it's not always this way in practice, but re-entry into the Schengen Zone usually affords you another three months, even if you haven't been gone three months after a three-month stay.
UUhhhhhh? So, you personally and acquaintences of your's have traveled by this rule du jour? I think it would be bad for if I went back in schengen after say 82 days in my first 180, getting a stamp and the border agent telling me i have a new 90 days, when in fact, legally, I dont, and 10 days down the road I am overstaying a visa and getting fined and deported.
That is not very reassuring. How often have you heard of this happening.
I like to bend rules, but not break them.
If you're that cautious, I counsel you to spend no more than 90 days of any 180 in the Schengen Zone. Transdnistria is a safe place for that.
But hey, SE Asia is awesome, too, so give it a shot.... the pricey bit is transport there, but prices come down once you are there.
Sounds like the whole world is an option, really.
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