In 2009, I was kindly hosted in Italy by some good friends. We visited Bologna, Ravenna, and other towns in Romagna.

The centre of Bologna is surrounded by many old gates, and most of the streets are lined with colonnades. Two leaning towers (one of which can be climbed) mark the very centre.
The University Of Bologna is the oldest in Europe (somewhat older than Oxford), and naturally has many fine buildings. The current seat is Palazzo Poggi, while at one time it was Palazzo Dell'Archiginnasio, which contains an old anatomical theatre.
Immense, but incomplete, the Basilica Di San Petronio was intended to be bigger than the Vatican. The pope of the day wasn't best pleased with that idea and had work halted (we are repeatedly told). The Holy Roman Emperor Charles V was crowned here in 1530.

Many churches in Ravenna contain extensive mosaics and date from the 5th century, when Ravenna was the capital of Italy. There remains the mausoleum of the ruler of that kingdom, Theodoric, who was born near Vienna.

The Neonian and Arian baptistries (above) are small, plain octagonal buildings with surprisingly ornate interiors.
San Vitale is another ancient octagonal building, but on a much larger scale.
Dante Alighieri died in Ravenna while in exile.

Rimini is a Roman town on the Adriatic.

San Leo is beautiful mountain village dominated by its fortress (in which Cagliostro was incarcerated).

The Republic Of San Marino was founded in 301 AD on a steep mountain, Monte Titano, near Rimini.