We did an Italy trip and I agonized over where to go and when. It ultimately was for a wedding in Tuscany so we did have some requirements to be somewhere at a specific time.
I researched a ton of options as we wanted to see as much as we could.
Ended up being a great trip and the research and recommendations really paid off. Did a lot of what was recommended in here. At the end of the day, pick where you definitely want to go and spread out from there and realize you can do all the major cities in one trip.
We flew into Rome for a few nights. Saw the usual sites including a midnight tour of the Coliseum which was amazing. Only a dozen or so people in the entire place.
Took the Italo train to Florence and directly on to Viareggio. This was probably my biggest mistake. Chose it because it was a beach town closest to some other places we wanted to see. This is somewhere Italians go for summer holidays and it was the off season. Next to no English and the locals rolled up the sidewalks at 5pm. I almost got into a fist fight in a beachside burger place who was making fun of my Italian and for some reason wanted to throw down.
We branched out from there to places like Lucca which was awesome as already mentioned.
We took the train to Cinque Terre and stayed in Vernazza for a few nights. Hiked to the some of the other towns during the day. It was not really cruise ship season but the place is totally different in the evening and night when the locals come out. There were bars and cafes that only opened in the evening lol.
We met up with my brother and sister in law and hired a fisherman to take us out and tour the area by sea and show us how they fish. We ended up sitting on his boat and chatting, drinking wine and eating cheese well into the night. He showed us a bunch of Etruscan, Roman, Greek and WWII artifacts he'd collected in his nets over the years.
We went from there to Florence but got off the train in Pisa, checked our bags at the station, took the dumb pictures at the tower and continued on to Florence. Glad we didnt plan anymore time there.
Met up with friends in Florence. My favorite city. Spent a few nights there, ate and drank and experienced so many things we still all talk about.
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