Sounds like a great trip. I can't advise you on most of it, but I would definitely check out the Crimea. While most of it is rather flat and boring, the southern coast is spectacular. I would check out Yalta and then ride east along the coast to the Kerch Peninsula, where you can catch a ferry to Russia (I think like an hour trip). There are many little resort towns along the coast, I would imagine there are some cheap lodging choices down there but not sure. The road along the coast is pretty cool, twisty through the mountains overlooking the sea.
Once you're in Russia, the Sochi area is pretty expensive as far as I understand, so you might want to stay in smaller towns. And then the ferry to Turkey, there are other threads here on that topic, sounds fairly straighforward.
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