Prague - Dubrovnik - Venice (11 nights in late August/early September)

I haven't done the itinerary but i have been to all three. While each individually is fantastic, they all do share something in common; throngs of tourists in an environment that exists for the sole purpose of entertaining the tourists. Okay, a bit extreme; and i did enjoy each. I just cant imagine going to 3 such places in one trip. Okay, that aside, reduce Venice by one night and increase Prague by one night to help compensate for the jet lag and for a little more balance i think.

Just for grins, look at your options for discount non stop airlines out of Podgorica and Dubrovnik and Tivat. The easiest way is to go to Google Flights, insert FROM Dubrovnik and TO Europe, then set the filters for oneway and non-stop. All the options will appear and they will be different on each day so look for the day before and after what you think is your schedule. Then do the same for Tivat and Podgorica.

I don't care for spending a lot of my vacation time traveling in and out of airports etc so I tend to stay a few places knowing that we will strive to go back. I'm more of a one to two country a trip person. My last three trips have been in just one area of one country.
I've not been to Dubrovnik but in Venice we stayed at Hotel PENSIONE GUERRATO and highly recommend it.
We traveled to Prague with family last August and had a great economical stay at the Pushkin Apartments. Amazing location. Not fancy but was perfect for three apartment on the same floor. Favorite bar in Prague: Hemingway's. Favorite place to eat: Dish Favorite beer garden: they were all awesome for different reasons. Favorite easy place to eat: Lokal. I loved all of Prague especially the beer, people and Art Noveau.

Thanks so much for your feedback!

I believe that there are discount airlines between the points or between airports very near the points (Dubrovnik vs Podgorica for instance). If that's true, then with 1 to 1.5 hour flight times you are at the equivalent distance as a 4 to 6 hour train ride. Still, its a bit scattered for my taste but each to what interests them. In Dubrovnik, pay the extra to stay inside the walls. Worth it in the evening.