Itinerary help, 2 weeks in Italy
 

I am helping 2 senior ladies plan their train trip in Italy. They are flying in and out of Milan.
They want to visit Lake Como, Cinque Terre, Venice, maybe Lucca or Bologna.
Any suggestions on a logical way to visit these cities, to streamline travel times and avoid backtracking?

If they can find one, They are considering taking an escorted tour that covers some of these places. Any recommendations for an agent or tour company are appreciated. I have not had much luck. Thanks

It is not possible to avoid backtracking when they are flying in and out of the same airport. At some point, they must backtrack to the starting point. A streamlined trip would have been to fly into Venice and out of Milan, but it is too late for that.

Starting the trip from Milan limits the choice of escorted tours. I think that is why you have not had much luck. Using an agent would likely to toss the itinerary into even more dysfunctional directions if these are the destinations desired. If they were interested in escorted tours, they should have started from choosing a tour first which would dictate airports to fly into and out.

If they are not driving, all these cities are extensively connected by rail. Use www.bahn.com to get the schedule. It is easier to use than the Italian site and you can feed both English and Italian city names. To get pricing, need to use www.trenitalia.com. You have to feed Italian spelling of city names, however.

When are they going?
Have they been to Italy before or any other places in Europe?
Are tickets already purchased?
If so, could they be changed to multi-destination (not two one-way), into one city and out of another?

Yes, schedules on the german rail site, tickets here [except for regional trains which are best purchased from the machines]:

http://www.trenitalia.com/tcom-en

The Cinque Terre gets a lot of tourism, some times just on the name alone, and attracts a lot of crowds. I'm not sure it's the best choice for a couple of senior ladies.

Here is one possible plan, making the most of not flying into Venice.

Directly to Venice for maybe 4 nights, taking 2.5 hours. Then 3 or 4 nights in Florence [2.05] with day trips, a hotel close to the SM Novella station located on booking.com. Day trips to Bologna [23 minutes] and Lucca [1.20], the latter easily combined with Pisa, Pisa first. Then to Lake Come [3 hours and up, depending on the station] maybe 3 nights. Finally Milan [1:20].

Looking at train schedules, it becomes apparent that a destination further away can sometime be reached in less time than one that is closer. E.g., Como Nord Lago directly from MXP takes 1:18, but from there to Venice can take 4.5 hours with 2 changes.

Thanks for your advice. They are well travelled, and the flights were part of a special deal for Milan flights. They are going in September and tickets cannot be changed.