This post was recently suggested to me by a friend. Although I haven't been to as many cities in Italy as I like, I have been to quite a few, and one more than once so I do feel incredibly grateful. Here's some of my recounts and tips for the few I have visited.
ROME: Rome has so much history! Also, I have seen the movie Roman Holiday with Audrey Hepburn so many times I definitely fell in love with Rome in real life and the movie. I feel like everything you touch there has some meaning to it. This city is easy to get around, just watch not to trip on the cobblestone streets...speaking from experience on that one. Must see sights include the Pantheon, Spanish Steps, Trevi Fountain, Colosseum(go early and avoid the lines), and the Vatican(again, early). Please keep in mind the first 3 of those are free, and the other 2 I really recommend the ticket price as being worth it!One of my favorite new areas to explore on foot is Trestavere. One night in the summer we discovered a beautiful open air market along the river. So many handmade goods for sale as well as fun small bars and open air restaurants. Perfect way to take in the city and watch the sun set, turning the sky on fire. If you go in the summer, beware you will melt as there is not much air con anywhere in the city as well as a lack of shade(old buildings=not tall=no shade). But don't worry, just eat lots of gelato to cool down!
MILAN: Milan is very beautiful! I only spent a total of one full day in Milan, so my "tips" are rather limited. I really enjoyed the Duomo and going to the top of the cathedral; the view was breathtaking! Be prepared for the dress code, you will need to keep your shoulders and knees(i think) covered. If you aren't prepared(like I was) you can rent a little fabric "robe" to wear there. It is probably the most awkward thing you will ever wear, but the church is a holy place and it is required. I enjoyed walking through the city, and eating lots of gelato! In the afternoon we went to Parco Sempione which was gorgeous, and kind of reminds me of Dolores Park in SF. Many people lounging in the lush grass, playing various games/frisbee, picnicking, and they even sell beer in little stands there. A great way to people watch and relax.
VENICE: Venice seems to be busy no matter what time of year you go. The water taxi's and buses can get really crowded so plan your route strategically and walk as much as possible. I had a not so fun experience dining at a restaurant on the water, and turns out they can charge you extra for all sorts of things, like a seat with a "view" and be sure to get tap water only! They will charge for a bottle(this goes for everywhere in Europe). I found better(and more authentic) food and restaurants on side streets and alleys, anywhere on the main streets seemed to have signs mentioning frozen food on the menu which made me extremely grossed out...but I digress. On the positive side, it's a beautiful little place to get lost, stroll around, go out for drinks at night...but since the area is so small it doesn't need to be more than a day or two here! On some of the side streets you'll find a lot of handmade crafts. I got the coolest swirl painted leather bound notebook here, and there's plenty of "masquerade" masks anywhere and everywhere. You'll want to stop all the time to get a picture that is better than the last, and that is the magical beauty of Venice.
CINQUE TERRE: Okay this is just one of those places you see on Pinterest or Instagram and you're like "How is that real?!" and you go there and it's exactly as you imagined if not better! I found out about Monarola and the Cinque Terre sometime in 2009-2010 after finding a photo via StumbleUpon. I was instantly captivated by the city on the hillside and showed a picture to my parents and tried to persuade them to make this place part of our next vacation. After seeing the picture I think my parents got even more excited to visit than I was! We took the train from Rome, about 4-5 hours or less. We were supposed to stop in Pisa(for the leaning tower) but there was a train strike and we had to divert our plans...save that for next time! Anyways, we stayed in Monarola, at a hostel on top of the hill. And I mean the very top! There are no cars, just cobblestone roads, and a hiking style trail linking the 5 little villages. Each are beautiful and different in their own way. These photos are circa 2010, but even though this place has become more known to travelers it still has not lost its charm and beauty. I would gladly go back here in a heart beat.
next up on my Italy wishlist: Florence, Amalfi Coast, Pompei!