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First stop: Milan vs. Florence

We’re planning a 25 day trip to Italy and Spain this May. The plan is to spend approximately three weeks in northern and central Italy and one week in Spain.

One leg of the Italian itinerary would include visits to Milan, Lake Como, Verona (maybe the Dolomites) and Venice.

The other leg of the Italian itinerary would include stops in Venice, Sienna, Pisa and the Cinque Terre.
Here’s our questions: Is it logistically better to fly into Milan and do the northern leg first, or should we fly into Florence and do that central leg first? From what we see, it looks like we’ll need to catch a train from Genoa to Barcelona. Can we catch a train from Milan to Barcelona, without going south to Genoa? What’s the shortest route? What’s the most scenic?
In either case, the plan is to depart Italy for Barcelona.

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You will need to determine which route to take if you go from Milan to Barcelona. You can drop down to Genoa and go along the Mediterranean or you can take the northern route that goes through France (Grenoble, Montpellier). The shortest option seems to have only 2 train changes and takes about 11.5 hours. The Genoa route wants to take you up to Milan anyway, with lots of changes. I have done the Genoa to Barcelona route along the Mediterranean, but we broke it up with stops in Antibes and Carcasonne.

To search and see the routes, use DB Bahn (http://reiseauskunft.bahn.de/bin/query.exe/en). Start with Milano to Barcelona Sants for your date and the time you want to leave. When you get the results, click on an arrow and open up all the train changes, stops and most of all, the map of the route. I very quickly did this for an arbitrary date in May.

To go from Genoa, make Nice a "stopover" and it will be plugged in as Genoa to Barcelona via Nice.

there will be lots of train changes on this route. You can also play with other stopovers and different routes.

Please note that you cannot buy tickets for this trip on the DB Bahn website, only see the route. You will have to get the tickets through the Italian train system which others and the Man in Seat 61 (http://www.seat61.com/) can advise you on.

If you want to see the Mediterranean coast, do the first and second legs the way you list them and then go from the Cinque Terre or Genoa on to Barcelona by train.

If you have little interest in that, end up in Milan and fly to Barcelona. Skyscanner (http://www.skyscanner.com/) can help you with that. From what I could see, it would take you 1.5 hours flying time and cost (at the moment) less than $50 for a non-stop direct flight.