If I was thinking of buying to ride in markets outside the US, I wouldn't be looking to ship from here to there unless I checked it out pretty carefully first. It might not be possible to license a US market machine in India for example, they have more rigorous emissions requirements than the USA does.
Also, at least in the destinations you mentioned, you may be able to get a LOT more machine for your money locally than you can here. For example, this machine, that gets exported to the US and sells here for what is considered a very reasonable price, around $7000, can be bought showroom fresh in India for less than $4000.
Another consideration might be image. A flashy foreign machine might be a rarity that says "here comes $$$ !", whereas a common local mount blends in. Nothing ruins a trip like having all your stuff stolen, and being constantly harangued to buy stuff or make a gift of money is a hassle.
If I was looking to make such a dream trip, I'd travel there, buy my machine there, outfit it there, then ride around the country, discovering, purchasing and slowly filling a container full of, old vintage machines to be shipped back home. I've heard the old machines can be legally licensed here via their "collector status" whereas new machines cannot be licensed nor legally imported. The proceeds of last years container would pay for next years trip. If it was India, the machines would be old Royal Enfields, Matchless, BSA, and Velocettes.
Maybe I'd even find a Vincent or a Brough? This dreaming business is a lot of FUN!