We are a group of 6 friends who are going to Italy in the spring for two weeks. I am organizing things since I have visited Italy several times. Given that 4 of the 6 have never been to Italy (and 2 have never been to Europe) we are visiting Rome, Florence and Venice, all traditional tourist destinations. We will not rent a car but use trains to get from place to place. I am considering an overnight visit to one small town (not the typically required tourist destination) somewhere along the general route from Florence to Venice. I know that Padua or Bologna would be great places to visit on the route and I may end up choosing one of them but I am searching for something smaller. I like visiting off the beaten track destinations and I would like my friends to see something far from hoards of tourists. Any suggestions for this area? Another idea I am considering is a visit to Trieste instead of adding a visit somewhere between Florence and Venice. I have never been to Trieste. Which do you recommend? We could go Rome, Florence, Venice and Trieste and fly out of Trieste since we are all using Ryanair to fly back to UK or the other option is Rome, Florence, small town, Venice and fly out of Venice back to UK. So many options, so hard to choose....
you should visit ferrara... Trieste is a beautiful city: Miramare Castle,Cathedral of San Giusto and grotta gigante worth a visit.
Between VE and FI there are Padua, Ferrara and Bologna that are worth visiting. Ferrara has a small town feel and it's pretty with plenty of historical things to visit like the Castello degli Este. You don't get the Unesco heritage site designatin for nothing. If you are willing to stray from the most direct route a bit, then Verona and Lake Garda could be an option. Around the beautiful lake there are several villages worth visiting (Sirmione, Salo, Limone, to name a few). Do an Image search online and see what you like among the above options.
How long would this visit be? In addition to Roberto's nice ideas, you might consider Parma if you would be interested in the food tours and dining there. There are day trips to Parma and Modena to visit the ham, cheese and basalmic vinegar. Here's a sample link http://www.parmagolosa.it/
Bologna also has great dining with lots of restaurants not too far from the train station.
I'll second Ferrara, a lovely place that seems to get few visitors (certainly few English speaking ones). It's right on the train line between Florence and Venice. You could also detour to Ravenna; in addition to the famous mosaics, it's a nice small town. If you're thinking of Bologna vs. Padua, I'll just say that I loved Padua - and didn't love Bologna, at all. I realize that my opinion about Bologna is minority one. I've never been to Trieste, but it certainly sounds intriguing. I think you have to decide whether you want a "busy" vacation, seeing lots of different places, or if you want to explore fewer places, but in more depth. With only two weeks, you can't do both.
You can easily do Padua as a day (or half day) trip from Venice; no need to change locations to visit. Another possibility would be Ravenna. While it doesn't offer a village experience, it has amazing 5-6 C Byzantine-style mosaics... quite different from Venice, Florence, or Rome.
I suggest Padova as a half-day trip from Venice (be sure to reserve in advance) and at least a stopover in Ravenna. You can stop in Ferrara on your way to Venice. If you've been to Venice before but not to Torcello, your Vaporetto pass will get you there.