Tallinn to Tblisi, potential 2021 summer trip.
 

I'm looking for thoughts on my choice of bike and any route/admin/advisories relating to a possible (and presently entirely hypothetical) trip to Georgia, starting in Tallinn:

Since buying my TDM and planning this summers short 10 day trip to Central Europe and back I've rediscovered a love for motorcycle travel that I'd shelved when my kids arrived. I then forgot where I'd shelved it.

But planning that trip, getting the bike ready and all that has brought all that back to the fore and it helps that my girlfriend is very excited about it all: her first 2-wheel trip.

Europe is nice, but I thirst for something a little different.

I've been looking East, or in this case SSE.

So first bikes: I have a TDM900 and a Transalp 600. For two-up travel, which would you take. I'm guessing the Yamaha as it's largely a paved route. Any arguments in favour of the Honda? One may be in the next paragraph.

As she and I both have full time jobs, the likelihood is that we would have 2-3 weeks to do this. It is very likely that this may require us to leave the bike there and ride it back at a later date (we probably have a place to leave it there). This is something in favour of the Transalp as my Yam is my "main" bike now.

Secondly the route. Perhaps I'm being biased and narrow-minded but the current political climate makes me a bit wary of traversing Russia. Then there's the whole business of their visas being valid for fairly short periods, as I recall.

Am I foolish to treat entering Russia with such wariness (being an Anglo-French citizen)?

Would Belarus and Ukraine be better, despite the unpleasantness in Donbass?

Is riding down to Istanbul and then East through Northern Turkey plain nuts in that time frame (if we don't want to live and sleep on the bike for 14 days)?

Any thoughts on these questions or, indeed, anything I've overlooked, I'd love to hear.

For 2-3 weeks? Fly to Georgia, rent a bike locally.

Riding from Tallinn via SPb/Moscow/Voronezh is over 3000km, meaning 3-4 days of absolutely gunning it, or 5-7 days with your passenger not hating you by the end. How's your Russian, btw?

Belarus/Ukraine is not viable to get to Tbilisi. You cannot cross Ukraine's southeastern border, only the northeastern one, so there is no advantage. It's either Russia all the way, or via Eastern Europe and the northern shore of Turkey. Or take the ferry from Bulgaria or Odessa.

I would say that if you only have two weeks, it is definitely not worth doing--just too far. And regardless of how much time you have, this is kind of a big trip for your girlfriend, as a first moto trip...of course I don't know her at all, but if it turns out she's not having fun, you should definitely have a Plan B...

I would not be worried at all about going to Russia, I expect that you'll love it. But if you just gun it down the major highways, it will be a pretty miserable experience--lots of trucks, police, traffic, etc. Better to take your time and take the side roads through the little towns--but at that pace it would probably take you five days or so to get to Tbilisi from Tallin, and that's if you don't decide to spend a day somewhere.

Unless you want to take the ferry from Odessa to Georgia, you won't be able to get to Tbilisi via Ukraine, at least without going through Russia; given the situation in Donbas, you'd need to cross into Russia around Kharkov.

Moscow is an amazing city, but the traffic, and traffic flow, is not for the faint at heart. I would give it a pass unless you really want to see it for some reason. If you go there, plan to spend at least a couple of days there, and stay in the center, or there is no point in going at all.

Where to stay is kind of interesting...I never made reservations, or even looked for places in advance, and usually found a nice place in a decent town or city. Personally I prefer cities so would try to plan the days to spend the night in one of the many small cities, and then spend the afternoon and evening walking around town. Smaller towns are very hit-or-miss--some are amazing, others are dumps. If you're coming from Latvia, I highly recommend that you spend the first night in Russia at Sebezh, a little town on a lake not far from the Latvian border. Nice little town with craft beer outlet right by the lake, it was great.

Anyway, let me know if you have more questions, be happy to answer.

Long way, for sure. Rental is certainly an option.

But part of the trip would be the getting there, hopefully. As we have a friend in Georgia there may be the option of leaving the bike there as some have done.

Exploring all possibilities!