Rome is a incredible nice city. All the charm is inside this city. The roman architecture is amazing. If you are interested of the History, this is the good place for you. Each corner of a street, you discover a curiosity. The food is excellent. The welcoming is also good and there is one feeling of romantism when you are walking in the city. You can find nice terrace around Piazza Venezia. If you are looking for a tasty Italian ice cream, the Cioccogelateria Venchi is the place. You can enjoy around of the Piazza of Spagna where a lot of tourists are lying on the stairs front the fountain of Barcaccia.
Trapani is a pretty city on the west side of Sicily. The most interesting places to visit are the old city Erice at the top of the mountain. You can reach this one by cable car. It's very close to Trapani. And the other nice place is Favignana Island where you can stay one day and walk around the island. The place is quiet and relaxing and easy to go there by boat.
Milan is a nice city. The heritage is rich. One of the famous places is the Milan Cathedral at the Piazza del Duomo. If you walk on the Dante Street, you will reach the Sforza Castle with backside a great park. You will admire the Arco Della Pace at the Piazza Sempione. Around this one, you will find few nice bars and restaurants. The Milan Central Train Station is as well an incredible place.
Venice is the famous romantic place. It's nice to walk through the small streets and canal by boat. You will discover easily some curiosities. The landmark is the Piazza San Marco where it feels good to enjoy a coffee in terrace. A week-end is enough to visit and enjoy Venice. The city is relatively small.