Skopje, Macedonia to Bar, Montenegro

Rome2Rio.com suggests a couple of bus possibilities. It is sometimes wildly off base about frequencies, travel times and fares, so try to find the schedules online. Unfortunately, in my experience the only bus schedule that matters in the Balkans is the one you get at the departure bus station. I would not attempt what you are planning unless I had slack in my schedule--in which case it should be a great adventure.

Another possibility would be the ride-sharing service, BlaBlaCar. I've never used it, I don't know that it operates in Macedonia/Montenegro, and I make no comments about its safety.

Be sure you're OK on the visa front. You'll have to go through either Kosovo or Albania, and I don't know what the visa situation is in either of those places.

One other possibility: As of 2015 there was daytime bus service between Nis, Serbia, and Podgorica, Montenegro. Rome 2Rio shows both bus and train links between Skopje and Nis. This routing would span three days, I believe, because the Nis-Podgorica trip was an all-day affair. (As of 2015, there was a Best Western in Nis.) The advantage is that you're not transiting Kosovo or Albania. And I can vouch for the beauty of the scenery between Nis and Podgorica. Alas, Podgorica is nothing special.

I don't know what order you are doing this trip in, but if you are going to Kosovo before Serbia you might want to check and see if that is still an issue. For the longest time, if you entered Kosovo by any means other than Serbia and then tried entering Serbia there were some "issues" at the Serbian border. The Serbs know because of the stamps in your passport. Not sure if that sort of thing is still going on.

We have been to Montenegro on a couple of occasions. Okay, we travel "well" but our driver and the Audi A6 cost about $80 a day. Montenegro was so inexpensive we actually had money left (which a local charity was happy to receive).

James is right. The car-and-driver solution is a fine one in the area under discussion. You really need time and flexibility to depend 100% on public transportation in the southern and eastern Balkans. It also helps to be a bit of an adrenaline junkie in the will-I-make-that-connection sense.

Maybe I am missing something In your post if so I apologize. But have you considered going from Skopje to Belgrade by train and then take the Belgrade-Bar train?? This route would be the easiest and most time efficient.

Travel in that area seems fairly complicated and we are up for that. I guess we wanted confirmations for some routes, in case we had missed something. It turns out we didn’t miss anything. We already knew about all the routes suggested. We really want to take the Bar to Belgrade train and are doing it in that direction because if we take the other direction, it will be dark by the time we get to Bar, (traveling in October) thus missing some of the spectacular scenery. For us it shakes out for us to go to Bitola and then hire a driver/car to Bar OR go directly from Sofia to Nis and then to Bar. (Missing Skopje and Bitola and this includes an 11 hour bus ride from Nis to Bar). Thanks so much for all of your suggestions.

Just hope you plan on spending 4 or 5 days in Montenegro. Great country from the coast to the mountains...