First time poster, not 100% sure whether this is the right area to post this.

I am from QLD, Aus. This trip is ideally scheduled to happen ideally anywhere from 2-3 years time from now. There will be 3 of us. The trip begins in Deilheim, Germany, where friend #1 has family, and takes us all of the way to Okayama, Japan.

After flying to Germany. We will travel south east along the Adriatic coast into Greece. Across Turkey into Georgia and then Azerbaijan. Freight across the Caspian into Kazakhstan - Uzbekistan - Kazakhstan again, into Russia - Mongolia - Russia and then Sakhalin Island. Then from Sakhalin into Hokkaido, and then down Japan to Okayama, where we will fly back.

So we will roughly go: Deilheim - Munich - Salzburg - Ljubljana - Dubrovnik - Podgorica - Tirana - Thessaloniki - Istanbul - Tbilisi - Baku - Aktau - Tashkent - Astana - Ulan Bator - Never - Vanino - Korsakov - Wakkanai - Sapporo - Hakodate - Tokyo - Kyoto - Okayama.

Here is what the trip will somewhat look like:

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This trip still seems ridiculous in size to me, but I am determined on making it happen. I am a filmmaker/photographer so the opportunities would be endless, and it would overall just be the experience of a lifetime.

Neither of the 3 of us have any intercontinental motorcycle experience, but we aren't worried about that. We would each have roughly $15,000 to take, excluding the costs beforehand.

Here are my questions:

Is this trip even doable? If not, what needs to change? Even if it is doable, is there a better, more memorable route we could take?

We are planning on buying bikes in Germany, I have done extensive research and think it may be possible. But is it a better idea to ship them over? Will we be able to possibly sell them again at the end of our trip?

Is $15,000 each enough to take? How long will that get us. We have no time limit. We are planning to prolong the trip as greatly as possible. Since we can just travel off of free short-term tourist visas in a lot of countries, we were planning to maximize our time in each country (usually have 30 - 90 days). We will definitely travel as cheaply as possible, camping, couchsurfing, cheapest possible food, no excess spending at all.

Sorry that this post just rambled on. Even if I could get a single response to one of the questions, that would be extremely useful. Since there doesn't seem to be an abundance of resources online regarding this exact route.

Thank you!
Noah

Regarding your route:
This year, the Korsakov - Wakkanai ferry Russia to Japan is not carrying motorcycles.
You have to take the ferry from Vladivostok to Sakaiminato.
Maybe the situation will change in the future, but that is how it is now.

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Japan touring information

Noah - first thing to know is that you will now need to do is this journey ! If you have thought about it this much then you dont do it you will regret it for the rest of your life !!
I am long term based here in Dubai and i have done a few distance journeys so please ask the questions and I will if at all possible assist you where I can.
My previous trips were Dubai to Dublin via Iran and Dubai to Capetown via Yemen. currently I am doing a trip of 15 days every six months on the PanAm highway - Ushuaia to Alaska and we have completed 2 sections already and my bike is now in La Paz. this will take us 4 years or more to complete. (I can only do it this way as Kids, wife and mortgage !)
enough about me ..
its important what bike you use as reliability is the most critical factor you need for a trip like this - at one end a DR 650 or at the expensive end a CRF 1000 - depends on your budget.
the 15,000 dollars would need to be exclusively for expenses on the trip and probably not include bike, gear and shipping costs but if you are frugal then its possible - immediately you can work out via google maps the distance then the Kms per litre and the cost of fuel along with the maintenance costs then work out a daily budget for food accommodation etc
it would be important to have the bike registration in your own name crossing the borders - can this be done if you buy in Germany ?

I am doing a short reply to you now but please if you can contact me directly on my email okelly.john@gmail.com if you wish
I currently have friends residing in Istanbul and in Tokyo who are bikers and would assist you in those areas with local orientation etc.
i am off to the HUBB meet in Ireland end of next week and although i haven't been to one previously I would seriously advise that you go to one.

Finally there is very little to be concerned about on a trip like this in terms of security - bikers are welcome almost everywhere in the world and other bikers will offer you help when they see you.
I have only ever found almost all people to be helpful and friendly - I tell a story when asked about this, that the worst thing happened to me was in Argentina
when I got badly detained/delayed by two policemen at a remote checkpoint in South Argentina - they insisted that I go into their cabin get my maps out, describe and discuss in detail my entire route, drink tea, take selfies, have a laugh and then they phoned ahead to a town to book accommodation for me that night !!
I was delayed by nearly two hours !!
keep planning !

Jonno

Like the man said... the Korsakov-Wakkanai ferry is a tiny passenger boat, does not take vehicles, they even grumble over luggage. There might be a big ferry on the line a few years from now, but don't count on it.

Right now there are ro-ro ferries from Baku to Kazakhstan. Way easier than freight.

There is definitely a good enough selection of used bikes in Germany that you won't be better off with the cost of shipping bikes from Aus. However, registration in Germany may be tricky for a non-resident. There are EU countries where this can be done way easier - my country, Estonia, is one of them. PM if you want details.

To get into Japan with your bikes you will need to have a Carnet de Passage, which is quite expensive. The rest of your trip should be doable without it. This is an annoying bit about Japan as the final destination. Of course you would need to ship the bikes out of Japan as well. Consider leaving the bikes in Vladivostok (you can put them on a freight train back to Moscow/St Petersburg from where they can easily be ridden back into the EU), taking the ferry or a flight to Japan, and renting or buying little bikes to travel around there. Or just travel around by JR Pass.

Hakodate is awesome, by the way.