Much depends on your own Passport.
For those travelling on an EU member state passport, a Business or Tourist Visa is needed for Russia.
But, as Rebaseonu says, there is no way anyone can cross a Russia/Georgia ground border. Until recently there were no flights between the two, but I don't know the latest situation - they may have been, or may be, restored.
And there would be no way of going the long way around Georgia as Azberadjan borders are only open to CIS (former Soviet Union states) passport holders.
There are numberous ferries from the Russian Black sea ports (Sochi is the farthest one clockwise) to many places - except Georgia!
Instead, I would stay in that part of Russia and enjoy the north Caucuses mountains. Truely breathtaking scenery. All main roads in good sealed condition and a full range of other surfaces on minor roads/tracks depending on what you like, and interesting towns and villages. Biggest traffic problems (apart from roads police) are animals roaming on the tracks. Horses, cattle, fowl etc - not bears, although there are some deep in the hills.
Probably better to keep away from Dagestan and Chechnia.