I am looking to visit these countries on a relatively quick visit. My starting point is a flight from NYC to Tallinn Estonia. From there I plan on driving or taking a train south and passing through each country with no particular agenda other than getting a little taste of the region.
Ideally, I would like to end up in Sarajevo to fly back to NYC.
Does anyone have any thoughts on how to best tackle this?
Thank you!


Estonia
Latvia
Lithuania
Russia
Poland
Belarus
Ukraine
Moldova
Romania
Serbia
Bulgaria
Kosovo
Macedonia
Albania
Montenegro
Bosnia and Herzegovina

How long do you have for this? I have been to all of those except Belarus and Kosovo, but I mostly used trains and buses. Buses in the Balkans, for sure. Read seat61.com for info on trains. Forget the car, too far and consider the drop off fee, plus you probably can't take it to all those countries.

'Yes, I'd certainly get the car. This is quite a number of regions and some will be alike one another - perhaps you should cut some out in order to provide more time to savour the experiences? Just my 2 cents.

Definitely car if doing all that though check yes whether you can take rental car to countries like Russia and Belarus - may want to cut those. Trains would take forever but if interested check these sites: www.seat61.com; BETS-European Rail Experts and www.ricksteves.com. You'd need at least a few months to do that unless becoming a train zombie or car zombie.

I agree with thursdaysd -- I would most emphatically not try this trip with a car!

For your transportation options, consult rom2rio.com -- just be sure to follow through on all the links, as the main website is not sensitive to seasonal variation in schedules.

>>I am looking to visit these countries on a relatively quick visit. <<

How 'relatively quick'? That is a HUGE undertaking. An hopefully you'd have more than a few weeks. And I honestly don't see how you could do it by car. Many rental agencies do not allow their cars in to one or more of those countries. Even IF you could locate such an agency - the drop off fee would be ENORMOUS.

If you're finishing off in Sarajevo, make sure you also go Mostar. It's only 2.5 hours by train, and it's a very dreamy sort of trip. If you only have a day or so in Sarajevo, you'll leave disappointed that you never lingered.

Romania can be slow going by train, and often peculiar timings don't help.

Bulgaria is slow too.

Macedonia has a useless rail network, but Skopje is well worth the effort.

Renting a car will be an issue as most have restrictions on which countries you can take the car to & most of those restrictions are in Eastern Europe. Renting a car or more precisely driving a car by foreigners Russia is never a good idea IMO. Can you rent a car in some of the countries you are visiting & take train/bus other times?

I have to wonder what the point is - covering so much ground just to "get a taste" but if that suits you, fine. I hope you have at least 4-6 months for this. A car won't work.

The main reason for not renting a car is nothing to do with border crossings and how easy/difficult it is. The car rental companies do not allow driving into the majority of the countries listed eg if you pick the car up in Riga you are not allowed to drive into several countries and those that you are allowed to drive into, there is a daily fee. Read the car rental requirements/driving abroad info under location information of the rental pickup station.

Is this a serious post? If so how long do you have for this or are you just going to show up at last country and then buy a flight home?

First of all, I’d like to thank you all for such thoughtful responses. They are all very helpful in my process for formulating a travel plan.
Secondly I should mention that I’ve done extensive traveling throughout the world. To date I’ve visited around 40 countries, all 50 American states and 6 continents. I was shut down in Christ Church New Zealand on my way to Antarctica.
Much of the travel has been comprehensive but admittedly some countries have been done through “rapid travel.”
I’m viewing this trip as a sort of “buffet” where I can sample some, pass through some and figure out what? and where? to experience.
From the responses here, it’s clear to me that simply renting a car and heading south is not a realistic option. It looks like I should plan on a combination of train and car.
I love to drive and I appreciate the warnings about Russia and Belarus. I also enjoy extensive train travel, especially in Europe. I love the ability to get some work done while I take in the scenery.
Does anyone know of a Eurail/Train route that heads south from Tallinn to Bucharest?

Suggest buying a Rail Map of Europe, maybe also this: https://www.europebyrail.eu/

I am a train fan but the train situation in the Baltics is not good and I used buses. You might look for my "B Trip" TRs - that trip included the Baltics and the Balkans, all by public transport.

Probably better to leave Russia for a separate trip. It's huge and a great candidate for a long distance train trip (I did the Trans Mongolian) and the visa can be a pain.

Does anyone know of a Eurail/Train route that heads south from Tallinn to Bucharest?

Go to www.bahn.de/en for schedules for all over Europe.

And if traveling that much by train look at various railpasses.

Please don’t travel by train throug Bulgaria. You’ll destroy your (if) positive impression of the country.

You need a rail map of Europe - Amazon carries some. As I already posted you want to use buses in the Baltics. I flew from Riga to Belgrade and went overland from there, so can't help with that leg. I agree that the train trip from Serbia to Bulgaria can be a major pain, didn't use trains after that, but the Belgrade-Sofia train goes on to Istanbul.

I located my somewhat dated European rail map. You have a choice of an eastern and a western route to Sofia, although from Vilnius you may have to go through Minsk for either. Eastern would go through Ukraine and Romania, western through Poland, Slovakia, Hungary and Serbia. Of course, you could also zig-zag.

Do not know what "Eurail" means to you, but each country runs its own railways, and a pass is rarely cost effective in this part of the world.

You might want to take a look at my trip reports relative to travels in SE Poland and Romania.