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I imagine this is not a unique problem but I was unable to find a straightforward answer.

I am a US citizen looking to travel to Europe for a bit over 90 days, let's say 100, but around 30-40 of those would be outside of the Schengen zone (Croatia and maybe Ukraine).

I will be landing in Italy and flying back home out of Germany.

I am concerned that I may have to deal with a suspicious official when I land and my return flight is longer than 90 days in the future. Additionally, I am wondering if I will run into any issues entering the Schengen zone for the second time (from Croatia). Do I need to keep any documents that prove I was outside of the Schengen?

Visual example of my plans; USA -> Italy (40 days) -> Croatia (30 days) -> Germany (30 days) -> USA

Should I expect problems?

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    You will/should get dated stamps in your passport when you cross the external borders of Schengen (so USA-Italy, Italy-Croatia, Croatia-Germany, Germany-USA etc.), which serve as proof of your period in/out Schengen. At land borders rarely the border guards don't/forget to put a stamp, in which case you should ask for one.
    – xngtng
    Jan 13 at 10:20
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    "Do I need to keep any documents that prove I was outside of the Schengen?": Yes, your passport.
    – phoog
    Jan 13 at 10:55
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    Should the Border Guard nevertheless forget to stamp your passport, retain your ticket (or first hotel bill) outside the Schengen Area until you return to the US. Jan 13 at 11:00

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I doubt you'll run into any issues. As a US citizen, you do not need a visa for the EU/Schengen and you are unlikely to be interviewed at length or have your return tickets inspected. If you're asked how long you intend to stay, state the length of time until you depart Schengen, not Europe, and if you have any evidence that you're planning to do so (flights, hotel reservations etc) it would not hurt to being them along. You do not need keep documentation of being outside Schengen, since unlike the US you will go through border control when leaving, so immigration will know that you were away.

The two questions that may pop up are 1) what are you going to be doing for over three months (just tourism? really?) and 2) how are you going to pay for this, since 100 days is quite a long time. Again, if it comes up, having some documentation of your finances and intentions would be helpful.

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    Immigration only knows because of the stamps in the passport. It can't hurt to keep a copy of these or other records in case of loss or theft if the passport, but it's probably unnecessary.
    – phoog
    Jan 13 at 10:53
  • "how long you plan to stay" Wouldn't "90 days in the Schengen zone + 30 to 40 days outside the zone" be a better answer?
    – moonman239
    Jan 13 at 18:27
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    @moonman No. From Schengen's point of view, it's not one long trip, it's two separate trips. Jan 14 at 1:40
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    I've had firsthand experience with flying out of Schengen without getting a stamp. The next time I entered I was asked about it and the officer seemed to accept my explanation with very little fuss (and some offhand comment complaining about Spanish exit controls). Still, YMMV, so I'd keep some documentation around supporting your story that you've left if this happens to you. Jan 15 at 17:04

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