Seeking Advice

So I promised myself someday I would go to Italy. Except that, when I put things in abstract terms like that, I never actually get around to doing them - I come up with excuses to postpone, and not to waste money on frivolities, and reasons it's not practical, until it's too late. So I promised myself last year that in 2012 I would go to Italy, because when I set concrete dates like that, it's harder to back out.

And now, with umbran anticipating gainful employment, it looks like this is actually going to be feasible. Which is both awesome and scary.

Here's the deal - I've never traveled outside the country before, with the exception of one (awesome) week in England when I was 22. I've never been somewhere that I don't speak the language, I've never had to navigate foreign cities, and I have precious little idea of what to expect.

So I'm taking this opportunity to pick the brains of my friends - any advice for traveling the world, and Italy in particular? We're looking at going sometime in October, both for our anniversary and because I've been told that's a decent time of year to head there, and I'd like to go to Venice, if only because that's where a huge chunk of my SCA efforts have been focused. Rome would be awesome too, if it's feasible to hit both. A coworker has recommended this tour company, which *seems* pretty cool, but I'm not sure whether that would fall into the category of 'making things incredibly easier' versus 'spending a lot of money to make the experience pre-processed and cheesy.'

Any hints, advice, or experiences in general would be welcome!