longbough

I just spent 10 days in Italy with my gf and it was fabulous.
Some places will be crowded with tourists - you'll probably have more fun in places that are less congested. I'd avoid Pisa, for example. It was overpriced and full of tourists.

Off the top of my head we went:
Florence - we stayed at a B&B called Hotel Bavaria - which had frescoes on the wall and was romantic as heck. But what's romantic depends on y'all. Some people prefer the Marriott but we like the simple B&Bs. If you stay here be sure to ask for the rooms with the frescoes.

Siena - we found another B&B - (we found it at the Tourist center - The fella tried to sell us on a crappy modern "3-star" place outside of town - Then he showed us a "one star" B&B which had a window full of flowers on the sill.

In Siena we rented a car and drove through Tuscany (forgive my spelling and/or memory) - Montepulciano, Castleveccio, hitting a few castles along the way. The drive alone shows some wonderfully photogenic countryside.

Then we stopped in Perugia - this isn't a very romantic city. It's full of students and more mixed with modern stuff. It was a nightmare to drive through it or find anything.

Then Assisi - OMG - what a beautiful town with a breathtaking view! Must be seen. We should have stayed here instead of Perugia.

Then La Spezia and to the Cinque Terre - a series of five gorgeous coastal towns reached by train. Travel between the towns was by some long hiking over steep grades but with some magnificent views. We stayed in the first town of Riomaggiore that had a magical view of the town and water. Cinque Terre is fantastic if you don't mind the hiking.

Then Carrera and it's huge mountain of marble. The town is trying to be a tourist draw but isn't very successful. But for us it meant that it wasn't crowded. We stayed at an odd place called Hotel Michelangelo which seemed like the only place in town - at least until the next day when we drove up to the mountain and saw some delightful B&Bs along the way with views of the mountain! You can buy wonderful marble items - cheap! The first place we saw seemed to have the best selection and prices - but we ended up lugging around marble bookends, cups etc. for the rest of the trip ... arrgh.

Finally we got to San Gimignano - what a wonderful place! Look for a B&B called La Mandragola ... this was the absolute best, most romantic, place we've ever stayed with a garden and rooftop terrace with a 360 degree view.

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"I do believe that, where there is only a choice between cowardice and violence, I would advise violence. Thus when my eldest son asked me what he should have done, had he been present when I was almost fatally assaulted in 1908, whether he should have run away and seen me killed or whether he should have used his physical force which he could and wanted to use, and defended me, I told him that it was his duty to defend me even by using violence." - Mahatma Ghandi