Yes, Tails is an option, if you don't mind the extremely limited usability. I have decided to use Tor Broswer in a non compromised system (which I believe Trisquel may provide). One option you would have was to go with Thunderbird (or icedove) and use Torbirdy extension. Its made by the Tor team and it's a addon that makes the connection go through Tor, so you can check your email without anyone knowing who you are. And of course, using the common addons for GPG. The only thing missing now from the Tor team is a "pidgin/tor protable". I can use Pidgin and OTR (which has proven to be good enough until now), but it still allows to know who is talking to whom. But that is not such a bad thing, after all, I believe the internet should be an extension of the real world, I don't mind that people know I talk to my cousin, I just want to keep the conversation private.

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