Only visa i see you need is for Russia, i suggest you get a double 30 day entry visa (no need for 1 year multi entry business for this trip) and not single to be safe as you can only get a Russian visa in the country you hold your passport (UK)
if you decide to cross again back in
As for insurance you can buy most at the borders you cross.
Which way are you going clockwise or anti clockwise?
For Georgia you cant cross into Russia along the black sea coastal road in Georgia as there is a country called Abkhazia which you can only enter from Russian side and then cant cross into Georgia from. it you go to Abkhazia (not only Google maps) in which you need a visa for then you will have problems going into Georgia so prob best to miss Abkhazia out all together for this trip
Abkhazia - Wikipedia, the free encyclopedia
For crossing Georgia to Russia (or other way round) you will go Kazbegi in Georgia to Vladikavkaz in North Ossetia in which the route is very beautiful
Sounds like a nice trip
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