Sounds just like my time at the then-Soviet Moscow State University, AC.
To FocalPoint, I'd follow your instincts and go with something guided from a reputable travel agent/tour company.
There is a fair bit of the wild west (east) about the place still, and if things do go mammaries skywards, you might be glad of assistance.
One thing I would thoroughly recommend doing is a river boat cruise of the "Golden Ring" (Zolotoye Koltso) cities, like Vladimir, Yaroslavl etc. Really nice big comfy cruisers with decent cabins, you can do anything from a night's trip to a week's trip I think. I've been on one myself, although in those days it was an easy and cheap way of accessing a bar/restaurant which actually had some booze and relatively non-comedy food in stock. No such worries in this day and age.
Driving is a waste of time as a tourist. Moscow and Petersburg are too congested, the Metros are fabulous and cheap. Cities are too far distant to be spending too much time on the (lethal) connecting roads. Overnight train journeys can be a bit special if you pay for the luxury cabins.
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Holidaying in Russia 
Holidaying in Russia 