:: trucking route ::
Vilnius was one I got to (a EuroPython), and really enjoyed. Aieste is a Facebook friend but I don't understand most of what she writes, given she speaks at least four more languages than I do. I've been to Pycons in Washington, DC and Chicago.
Pycons may happen in parallel, although in terms of PSF people getting together, that's not always in the cards. Pycon / Singapore (Asia-Pacific) happened over the summer. I helped mind the (curriculum writing) store at OST while Holden Web took a tour, including Nippon.
People wanting a Pycon in Baghdad or Tel Aviv don't have to worry too much about sequence ("simultaneously" is OK). Even when the distances are not so great (quite drivable by North American standards) it's enough work to get visas to have to pick and choose.
In the meantime, short of full-fledged Pycons, we have local user groups. Some of these are informal, on-campus or off, and may not yet be listed on the community Wiki, unlike Portland, Oregon's or Chicago's, both of which have been going a long while.