My husband and I headed over to northern Italy, Malta, and Sicily for 24 days starting in late September and going through much of October. The trip was, in a word, fantastic. The Sicily portion we had no reservations or set plans (outside the 1st night & last 2 nights), and it was the first time we traveled by the seat-of-our-pants. We would do it again in a heartbeat, the flexibility it offered suited us well.
Here are some details in order of our visit (with hotel info in parentheses) and, for anyone interested, a day-by-day account can be found in my profile by clicking on my name.
Venice (2 nights; Ca San Trovaso): husband and I have been before; my parents first time. Venice is still as charming as we remember. The day we left we picked up a rental car from EuropCar at the airport and used it for the following 4 days. Our first stop was to Casasola, a familial ancestral home.
Garda (1 night; Hotel La Vittoria): this was more or less a pit stop, but we loved Lake Garda and will definitely return. After leaving Garda we stopped in Verona, and, well, we all couldn't wait to leave. It seemed very tourist-trappy.
Cuneo (2 nights; Hotel Royal Superga): the Piedmont region is beautiful and we had some excellent and varied food. From Cuneo we were able to visit Sampeyre (familial ancestral home), make a very brief stop in Savona, and stop in Noli for a couple hours. Noli is a gorgeous, small seaside town (one of many in the area, it seemed) and this stretch of Italian coastline definitely needs to be investigated by us in the future. Cuneo itself is a mid-sized city with a central square and great restaurants. We'd definitely go back to spend more time.
Milan (1 night; Air Hotel Milano): we dropped off the car at Malpensa Airport, said goodbye to my parents, and made our way across Milan via the Malpensa Express train and then shuttle bus to Linate Airport, from where we flew to Malta the following morning.
Malta (4 nights; Sogdiana Inn, St. Julians): oh, Malta. We spent 4 nights here and it was 3 1/2 too many. We didn't cotton to Malta, mostly because there is quite the trash problem and the public bus system was an arduous chore. I would never, ever go back. Nevertheless, we visited Valletta, Marsaxlokk, San Anton, Mdina, St. Julians, and Gozo.
Nubia, Sicily (2 nights; B&B Casolare nelle Saline): Nubia is just south of Trapani, and it was a great home base for a couple nights. We were able to get to Riserva dello Zingaro nature reserve (highly, highly recommend), Erice (not a fan of; very made-for-tourists-y), Trapani (great town, great vibe, wish we had more time there), and the nearby salt pans.
Caltabellotta (2 nights; B&B Le Foglie D'Argento): Caltabellotta is in the interior bits of Sicily, and it was nice to be able to spend time in the area. The B&B was fantastic and very picturesque, we spent a great deal of time relaxing here. But we also managed to visit Sciacca (known for ceramics) & Lago Arancia, too.
Marina di Ragusa (2 nights; Hotel Miramare): we were in the mood to spend some time at the beach so we chose Marina di Ragusa, in the SE corner. It's a cute town, seemingly popular with Italians, and we enjoyed our stay here immensely. The town of Ragusa was not too far away so we day-tripped there. The cathedral in is impressive. We also stopped in Siracusa (well, Ortygia, actually) on the way to our next overnight destination and loved, loved, loved that town. There was something about it that was very appealing and we'd go back and spend a few nights there next time.