This is my idea about your Italian trip: Starting in Milan, don't spend too much time there since it's not such an interesting place, but a big, grey, industrial city. See the Duomo and a couple of other places.

Cinqueterre, as others said they can be crowded; no doubt the scenery is amazing, but there are other places in Italy as wonderful but just less known... you can check out Portovenere, a small town very close to the Cinqueterre, and really lovely. Also Portofino and Rapallo are great!

No problems about going to Rome by train: it takes about 5 hours on the coastal line, and you can enjoy the view of the Tirrenian coast.

If you need more info about Rome you're welcome to ask me, and I am sure Giorgio will also help you on directions to-from his hotel and to enjoy Rome. Also, you said your children will travel with you, so I will be happy to give them some tip to enjoy the Roman nightlife if they like! (Let's Go is not really updated!)

>From Rome to Florence there are trains every hour, and it takes about 85 minutes. You can choose among several tran categories depending by your comfort needs and price you intend to spend.

Tuscany, Umbria and Marche are very nice, and Urbino is not just a students town but also a nice Reinassance city. There's a good nightlife due to the students, so I am sure your children will love it for that reason too! (I did!)

Not far from Urbino you can check some cool place: San Marino, an independent country within the Italian territory, built on a mount is a nice Middle Age Republic with amazing views from its towers; San Leo, a castle with a great ancient weapons exposition; the Riviera Romagnola, with several small towns and a few major cities (as the famous Rimini) where you can taste the typical Piadina on the seawalk, if you'll have a nice weather; ...

You mentioned Bologna. The city is very nice nad interesting, and maybe many people don't know that it hosts the oldest university of the world (Paris came second). The city center is small but very pretty (Piazza Maggiore, the 2 towers, ...) and a bit outside is a nice (but long) walk towards an old monastry under the longest porch (Bologna is the city of porches). Food is great, and cuisine includes the famous tortellini and several other specialities.

>From Bologna to Milano, for your return trip, there are several trains and the ride takes about 90 minutes. If you still have some day you can check some other town as Padua, Verona, Ferrara, Ravenna, Parma, Piacenza, Mantua, ... there's so much!!!

I hope this helps, and you are welcome to ask any question you may have. Good luck!

Ciao Flavio in Rome