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I have a multiple-entry one-year Schengen visa and I did have travel insurance first time when I crossed the border of Schengen, but it has expired already and I wonder if I need it during my next trips to Europe?

Is this something that you are obliged to have or it's ok not to have it?

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Are you talking about crossing internal borders between two Schengen countries, or about crossing external borders, entering Schengen from a non-Schengen country, or exiting from a Schengen country to a non-Schengen country? –  hippietrail Feb 10 '13 at 2:05
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Yes, about crossing external borders, entering Schengen from a non-Schengen country. –  Volodymyr Feb 10 '13 at 19:52
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1 Answer

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Technically yes, the terms under which a Schengen visa is issued require you to have health insurance up to a certain amount of coverage. You may be asked for proof of this in the form of health insurance documents when you're entering the Schengen zone and/or at any passport control checks.

In practice though, it is unlikely that you will be asked to provide documentation for this. However, travel health insurance is still a good thing to have as hospitalisation costs in case something does happen can be expensive. You don't need to get an expensive policy; at least in the UK, you can get short term travel health policies which cost less than £10. Even though these policies may have high deductibles, for serious accidents they will still help you recover medical expenses.

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Hm, what if I am asked to provide documentation and I do not have it. Will the border control refuse me in crossing the border under such circumstances? –  Volodymyr Feb 9 '13 at 22:51
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@Volodymyr Yes. Your entry could be rejected or your visa revoked on those grounds. –  Ankur Banerjee Feb 10 '13 at 2:09
    
I'm travelling between EU and UK every week for the last six months. Never been asked for health insurance once. However, it's safer to have it. That's why it's called accident and insurance. In case, something unthinkable situation happens. –  toy Feb 11 '13 at 13:49
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