Flight options Dubrovnik to Milan

You don't mention dates, but picking a random day in May, neither Google Flights nor Skyscanner show any direct flights. But there are several flights with a single connection, the fastest being an Austruan Air flight of just under 4 hrs. Same for Split, but you might have more choices with shorter flights.If Milan is your choice of destination, then you'll have to resign yourself to a connecting flight.

In June

• Wizz flies non-stop from Podgorica on Tuesday, Thursday and Saturday. Leaving from Podgorica would create a bit of an excuse to visit Montenegro and see what Croatia looked like before the tourist completely took over. Just a few hours from Dubrovnik.
• Ryan flies non-stop from Dubrovnik on Saturday and Wednesday.
  

Well at least according to Google Flights.

I don't know what time of year you're taking your trip, but there are some seasonal non-stop flights between Dubrovnik and Bergamo, a lovely town east of Milan (with rail service). Unfortunately, those flights are on RyanAir (which has some burdensome rules calculated to separate you from as money as possible), but it will get you there. I don't know anything about the availability of public transportation from the Bergamo Airport into Bergamo or to Milan; it's conceivable that could be a bit of an issue with flights arriving very early or very late.

Montenegro is a beautiful country, but if you decide to head down there for a flight connection, be aware that Podgorica is far from its most attractive city (that's an understatement).

Hello,

Thank you all so much for your response. Apologies for not giving all details. Travel would be in mid May.

For others looking to do the same, air travel into Italy from Dubrovnik is certainly doable as folks have posted, but just consider the day of week & stops.

We appreciate this forum and hope to reciprocate along the way as we gain more current knowledge.

It’s been a few years (25!) since we’ve been to Europe and looking so forward to the journey & moments.

Happy Travels!

Milan is great, Croatia is very, very okay. Montenegro can be great if you are into off the beaten path and vistas. Cinque Terre is a bit of a tourist trap or so I am told (but I was told the same about Hallstatt and loved it), Florence in May should be very good, The dolomites I just dont get the attraction for. Venice, one of those places that must be seen no matter the cost or crowds or Disneyfication. Most of your stops, all great, are mainstream tourist attractions. You might consider starting the trip or ending the trip someplace off or closer to off the grid. Its more about time than cost, as off the grid places will cost you half of Venice for instance. Just a suggestion. Sounds like a great trip.

The best solution I can find is to take a direct flight to Rome, then a train to Florence and then continue on with your other locations.

Florence-CT- (Milan?)-Dolomites-Venice

No idea if Milan is a 'touring' destination or simply the most convenient airport in your plans.