Black Sea Circumnavigation

It looks like the only country you would have to obtain a visa from is Russia, and you would have to do that beforehand. You also might have to go through Moldova and I don't know if a visa is required. Ukrain, Romania, Buklgaria, Turkey, and Georgia don't require a visa if you are a U.S. citizen. I've briefly looked at a map. You may have to have a combination of trains and buses, and depending on how the tracks and highways are laid out you will probably need at least a month to get around the Black Sea. You are an experienced traveler so the excitement of trying to drive would be right up your alley. We have been to all the countries around the Black Sea except Russia and Georgia. Bulgaria is a little behind the rest as far as being able to accomodate travelers, especially in the eastern part. I hope you have plenty of time to do your planning. If it were me, I would use public transportation. Good luck.

The Black Sea towns and resorts in Bulgaria are modern and wonderful. The rest of the country is spectacular as well.

I believe Matthew is correct - I don't think it is possible for you to travel between Russia and Georgia. Your alternative (if it is possible) would be to drive into Azerbaijan and then back track. OR try and sail between Ukraine and Georgia (this used to be an option - requires research) bypassing Russia (both options defeats what you are trying to do).

Mike, I'm not sure this helps you, but I have navigated the Black Sea (in a warship) several times. I remembered seeing some ferries in Batumi and Poti, Georgia and found the website of their shipping line (below). I can't vouch for their safety record, but they do travel from Georgia to Kerch (Eastern tip of Crimea) or Ilyichevsk (just south of Odessa) in Ukraine. Since Georgia elected a more Russia-friendly president, it may be easier to get across that border now, but you'd still have to travel through Abkhazia. Good luck to you! The Black Sea is a beautiful area.
http://www.ukrferry.com/eng/schedules/index.php -TJ

You will need a Russian visa (a big bother) which cannot be obtained at border crossings; it must be obtained before you leave. It is currently not possible to cross into Georgia from Russia along the Black Sea coast south of Sochi through Abkhazia. An Abkazian visa can be obtained online for around $10 but it makes for a dead end in Georgia because the Georgians don't recognize it as legitimate. I know a few people who have entered Georgia from Sochi by this route but technically this is not legal and you run the risk of a fine or at least being hassled. You can cross into Georgia at the Lars frontier crossing up in the mountains and enter Georgia through Kazbegi along the Georgia Military Highway. The crossing has recently be rebuilt and is open to anyone...Anyone that is with the guts to go through the Northern Caucuses in order to use it! The only other entry is by the Roki Tunnel leading from North Ossetia into South Ossetia. If you are not a Russian citizen it is virtually out of the question to use this crossing, although you can apply for an entry permit and if your Russian is good enough and you have the power of persuasion you just might get in but a time limit will be set for your stay. Keep in mind that you cannot enter Georgia from Russia via South Ossetia and getting back requires a multiple entry Russian visa. The only realistic way to move from Russia to Georgia along the coast is to take the ferry from Sochi to Trabazon in Turkey and then drive back to Georgia and enter through Sarpi. There is no need for a Georgian visa for US citizens and it is a $20 entry fee for Turkey. To enter Bulgaria from Turkey you can cross at Malko Tarnovo and drive east to Burgass along the coast, otherwise crossing at Edirne means back tracking. The crossing from Bulgaria to Romania is straight forward but you will have to decide how much, if any of Moldova you wish to see before going to Ukraine. Have a fun!