All of the accommodations listed below are places where we’ve stayed or close, trusted friends have stayed. This is a small list of our favorites. Most have three star ratings.
Italy
Lombardy: Milan
Hotel Charly, Via Settala, 76, phone: 0039.02.20.47.190
http://www.hotelcharly.com/en/
Small, cosy hotel near the train station. It’s on a quiet street and convenient to the metro. Nice people and great price for Milan.
Umbria: Montefalco
Villa Mustafà, Via Casale, 71, Montefalco, Italy. Phone: +39.07.42.37.8329
http://www.villamustafa.it
Wonderful agriturismo just outside of Montefalco, a quaint hill town in Umbria. Large, comfortable rooms with views of the vineyards. Gracious hosts who give helpful advice on itineraries for the area. They also provide a generous breakfast with home-baked goodies and farm fresh eggs. The outdoor patio is a perfect place to relax and enjoy the fabulous country views.
Umbria: Perugia
Villa Nuba, Strada vicinale Colle San Giorgio, 70, Perugia, Italy. Phone: +39.07.55.72.5765
http://www.perugiarentals.com
Beautiful and well appointed apartments with a lovely pool and grounds just fifteen minutes from the old city center of Perugia. Giuseppe and Elga are the greatest hosts you could have for Perugia and the Umbrian region. This would make a great base for visiting Umbria.
Rome
The Beehive, Via Marghera, 8, Rome, Italy. Phone: 0039.06.44.70.4553
http://www.the-beehive.com
This is a budget friendly, small hotel/hostel. Rooms with a private bath are available. Run by an American couple, it has a friendly and hip vibe. Small, basic rooms, a healthy and organic breakfast is available on site for a small fee. It also has a nice patio for relaxing outside. The location near Termini Train Station is quiet and safe, yet very convenient.
Tuscany: Lucca
Stories of Italy
Racconti 
Allow me to help you with Trapani ~ La Gancia, suite on top floor with private terrace…check it out! When I wasn’t on the terrace, I was thinking about being on the terrace. Rooftop bar, breakfast served there also. http://www.lagancia.com/en/
Thanks so much, I’ll check it out! Hope to read some posts on your Sicily trip!