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I'm a citizen of Ukraine planning on visiting Italy early in October for tourism. Later that month I'm accepted as a speaker at the conference in Prague, Czech Republic. Both countries are members of Schengen agreement and a visa is required for me to visit them. Therefore, I need to visit Schengen countries 2 times and I need to get my visas ASAP (to confirm my talk to the conference organizers, as well as to avoid overpaying for hotels/flight tickets).

I've heard a number of times that a single person can't apply for a Schengen visa if already in possession of one, but I'd like to clarify this. Say, I've got a visa from Italy for the period of October 1st - October 14th. Can I get another one from Czech Republic for October 25th - October 30th before I visit Italy? Would the answer be different if I were to visit the second country (CZ) on October 13th - October 20th, thus, having a single day overlap between these visits. It would be of a tremendous help if you could link to the official documents that prove your point, but I'd certainly appreciate answers even without such links.

Both times I'm going to apply for a short-term tourist visa covering the dates of my travel. If the answer to both questions above is no - would several visits to multiple Schengen countries over a short period of time be a valid reason to apply for a single multiple-entry visa that covers the whole period from October 1st to October 30th from Italy?

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You won't be able to get another single entry visa while you already have an unused one. However, you can state your itinerary when applying for the visa with Italy (since it is point of first entry as well as the country you'll be staying longer in) and on that basis, apply for a multiple entry visa

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    Thanks, I'm not sure if I won't be frowned upon by Italy for making my second entry to another country, but that's definitely an option.
    – alexk
    Aug 13, 2012 at 13:12
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    No you won't be frowned upon. That's how Schengen visas work: you apply to the country that is your first port of entry in case of a broken journey, or the country you'll be spending most time in case of a continuous journey - and then you tell them what your itinerary is. The Italian embassy is not obligated to give you a multiple entry visa though.
    – Ankur Banerjee
    Aug 13, 2012 at 13:19
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    My own experience is that I had to go for a week to Germany for a conference, and the German embassy gave me a six month multiple entry visa even when I'd asked for single entry. For free. So this is very much your-mileage-may-vary and what country's embassy you're applying to.
    – Ankur Banerjee
    Aug 13, 2012 at 13:20

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