USA traveller in Europe longer than 90 days total
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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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Source: stackoverflow.com
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