Best route to take by train/plane

If it were my trip I would first start with the obvious, a map, then I would go to Rome2rio and check distances, time it takes to travel, connections (direct train or train and bus for example) to get an idea. Another website I like is distancesfrom.com. You plug in the cities and it shows you in a map. You can see if you are, say, backtracking. Some travelers also factor in time of year and weather. Say, going from north to south if you start in August. I would also check some of the European airlines and their routes, such as Ryan Air or Wizz Air. See who flies to Sicily (pick a city). This would have to be your last stop. This info could help determine your route. Hope this gives you a little help. Others may have better advice.
PS. You should put this topic under general Europe. You will receive many more responses

PM me and I will give you contact info for someone that can help with most of it.

Here is my stab at it. While a map is essential, you also have to understand that the connections may dictate the route, not just proximity. In this case either Vienna or Budapest had to be last for a good connection to Sicily.

The other kicker is not all of the flights fly every day.

Naturally the two outliers are Prague and Sicily.

Istanbul to Prague on Turkish Air (I suppose others fly the route non-stop too)

Prague to Vienna by train (about 4.5 hours)

Vienna to Salzburg by train (3 hours)

Salzburg to Ljubljana by train (about 4 hours)

Ljubljana to Zagreb by bus or same guide as below.

Zagreb to Split to Dubrovnik by guide as this isn’t the easiest country to travel in (the contact I will send you if you PM). Not expensive.

Dubrovnik to Budva to Podgorica by the same person

Podgorica to Budapest by Wizz Air

Budapest to Sicily by Wizz Air

Wish I could take two months off!!

Use Google Maps and use Google Flights and see if you can do better. This took 5 minutes.

I am hoping someone has done this journey and have suggestions where to and from . Starting Zagreb and going wither to Slovenia or Budapest etc....have looked at some maps but not finding it easy .

I very been to all of the places except Slovenia. But finding someone who did them all in one trip will be challenge. Happy travels.

We actually did a similar route in 2014. We started in Prague, driver to Cesky krumlov, same driver then to Vienna, then we took a catamaran to Bratislava for one night, then the bus to budapest. My sister and her husband then flew home and we took the bus to zagreb. We then rented a car and drove to Rijeka. Driving is easy in croatia, all new roads courtesy of the EU. Anyway, you could then drive from zagreb to Ljubljana, down to Split then to Dubrovnik. With this route here lies your problem, there are no direct flights from dubrovnik to sicily. You have to go through Rome.
If you reversed the route, dubrovnik, split, ljubljana, zagreb, budapest, vienna, prague - there is a direct flight to sicily from prague. There is direct flight from Istanbul to Dubrovnik.
Hope this helps.

Thank you this is so helpful. I like the way you did things and am now feeling better about my plans
Paula

One website to check to see if there are direct flights, buses, trains, etc is Rome2rio. I also like distancesfrom.com for when we have a car. You can plug in your route and map it out. It gives you approximate driving times. Come back with any other questions.