Lucca - friggin love that town. I could end my days there. They have a wall around the old town which is basically a park above the town. Rent bikes and do a couple of laps around the town. Like most places in Tuscany and area it is really busy with tourists during the day but at night the buses are gone and it calms down.
The same could be said for Volterra and San Gimignano other popular day trip locations in Tuscany. We stayed in a farm on the outskirts of a little town named San Casciano In Val di Pesa which is south of Florence kinda in the middle of most of the places to see. The house was on the grounds of the family run olive farm. Getting to wander through the fields was a great experience, especially after the hustle of Florence.
The Cinque Terre would be a must too. The towns were hit hard by mudslides a couple of years ago so you're euros are going to support people who can use it for some more basic purposes.
We have also been up to Lake Como by Milan. We had a happy accident as we were aiming for Varenna but ended up at a little town named Olcio at a great B&B. They sent us off to a local restaurant for dinner which was so good we went back the next night too. It's a meal and place our friend and us still talk about.
If you're going that long Venice would be worth a couple of days. It is also quieter at night. Milan was fine, but nothing super memorable. Pisa really just has the tower and Duomo. Don't, for the love of Kiprusoff, do the goofy tower pose where you are holding it up or pushing it over. It looks stupid. The Duomo is much more interesting than the tower in my mind.
For the south get 4x4 to give you his rundown of Rome. I think I still have my copy he sent me. It's awesomely detailed and funny as hell. I should just post it up as it's hall of fame worthy in my mind.
Another place I very much want to visit on the next Italian trip is Civita di Bagnoregio. It's not off the beaten path as it's a Rick Steves favourite, but it looks awesome all the same.
If you're thinking of Sicily I have a pile of stuff for it too but I think I'll stop.
4x4 and Aeneas can fill you in on so much more.
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