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I plan to visit Europe for the first time in March and since the cheapest tickets (non-direct) usually involve a layover in Iceland, I decided to spend a week in Iceland, before continuing to mainland Europe (Spain and beyond). I'm still in the process of figuring out my itinerary within mainland Europe, but I plan to stay in Schengen Area for about 2-2½ months, then take a train to the UK, and then finally return home.

I know that as an American I can enter the Schengen Area visa-free for 90 days, every six months. I have considerable savings (25K+ USD) to support my stay/travel but, since I travel alone, I plan to stay mostly (but not exclusively) in hostels, CouchSurf, Airbnb etc, around Europe to meet people. I'm trying to keep my itinerary flexible.

How much proof of my itinerary/lodgings/etc do I need to show and do I need to have proof of an onward train ticket (say Paris-London via Eurostar) when first entering Schengen in Iceland?

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    Entering Iceland, we were not asked for proof of onward travel (or much of anything else). I'd have documentation of the $25K, though. With that much, you can always buy a refundable airfare if you need it. – Andrew Lazarus Jan 27 '16 at 5:43
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    You would have to convince the officials that you do not intend to overstay. A prearranged itinerary is one way to do that. Do you look like an overstay risk, otherwise? Steady job? Real estate? – o.m. Jan 27 '16 at 7:16
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    Aside - it's not 90 days every 6 months. It's 90 days out of the last 180. So while yes, if you want to spend the maximum limit on each trip it's effectivley 90 days every 6 months, if you want to do shorter, but more frequent trips, that is also an option. – CMaster Jan 27 '16 at 9:27
  • @CMaster Thanks for clearing that up! That makes sense. – unknownprotocol Jan 27 '16 at 17:48
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    I went through Icelandic customs two weeks ago as an American while between jobs. They asked me no questions— just looked at my passport and let me in. I did have roundtrip tickets, but I don't recall their checking that. Perhaps they had already reviewed that electronically. – Alan Gerber Feb 17 '17 at 21:22
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There are no requirements to provide proof of onward travel when entering the Schengen area.

What you do need is adequate 'means of subsistence' both for the intended period of stay and for onward travel out of the Schengen area. Each Schengen country has their own guidelines when it comes to the required amount of money. Iceland operates with a guideline of 4,000 krona per day, meaning that you with 360,000 krona or about US$ 2,800 have enough money for the allowed 90 days. Even if you need additional money to buy a return ticket, you are well beyond the required amount if you dispose of US$ 25,000.

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