Italy by City
Italy is probably better known for it's main metropoles like Milan, Venice and Rome than it's lesser traveled countryside. Despite enjoying the "less discovered" heaps more than the main touristic spots, these cities do have a bit of charm and enchantment.
Milan, the city that never stops… shopping, that is. Unless you came here to shop, or for a fashion event, it's hard to imagine what one would stay in Milan for. But nevertheless, I'm sure there's an appeal to it for some. If you do stay the night, check out Ostello Bello. It's a really cool hostel that goes above and beyond to ensure your stay is exciting. Let's just say they had me sold at "free food!"
Venice, in some situations I can see how Venice can be a super romantic city. Getting lost in the grid of islands and canals, eating delicious Italian cuisine, taking a romantic gondola ride, and watching the sunset from one of the many bridges. It can be cute. But, since it's also one of the most visited cities in Italy, it can get really crowded, even during low season. It's definitely worth checking out though, there is a certain appeal to this city and it's strong pisces aura. But, be ok with getting lost, ditch the maps habitually and stop to look, otherwise you're running the same race everyone else is. A cool place to spend the night in the city is Generator Hostel. You'll need to get to them by ferry, so consider buying the Venice Rolling Pass, for unlimited ferry rides for three days.
Rome, when in Rome, do as the Romans do. Eat as they eat, play as they play, and enjoy as they enjoy. Rome is an ancient world stuck in a city. An amazing place for those who appreciate it's history and for those who are just starting to learn. You can spend an entire week in Rome and still feel like you need more time. So roll up your sleeves and feel the life of the old world. It's quite an amazing and spiritual place. It definitely pays to know your history, I will say. It brings a deeper sense of appreciation and understanding to the ruins that lie around the city.
So all-in-all, I would say definitely to Rome, maybe to Venice and probably not to Milan. Go deeper into the country, you will probably enjoy it more. With it's relatively inexpensive food and transportation costs, it's possible to see and enjoy a lot of Italy.