small undiscovered charming town

I second the vote for Lucca!! It is a walled city, actually I believe it's called a rampart. It is wide, enough so that there is a road and green area on both sides. We rented bikes and rode around. We climbed to the top of Guinigi Tower for stunning views of Lucca and the countryside. We attended a Puccini night concert at the Church of San Giovanni. The city is easy to walk. The train station is right across the street from the wall, so easy public access. We found good food. I will return.

Lucca is hardly "undiscovered." We'll be going to Bergamo this May, after having heard lots of wonderful things about it. The upper historic center is a walled medieval hilltop town with views out over the surrounding valley, unlike Lucca which is on a flat plain. However, it's NW of Milan, so might be out of your area.

You will have a car, correct? I suggest Barga in the Garfagnana area north of Lucca, in th emountains: http://www.buk.irk.ru/village_barga/barga.htm Or perhaps Castelnuovo in the same area (it has a wall, I believe): http://www.castelnuovogarfagnana.org/index.php?pag=34

Another for Lucca, based on personal experience. I haven't heard of Lola's suggestion - but she would know. Probably take hers over mine unless you prefer the things Lucca has to offer including towers, gelato, bike around the walls or walk around the walls, easy train station. If Rick has been somewhere it isn't undiscovered. Rick has done a TV show about Lucca.

Pistoia is a small city of about 90,000 people, but has a charming walled core area.

Nigel-thanks for the vote of confidence. We spent two nights in Lucca and loved it. Climbed the tower, biked the walls, walked all the small streets. But where I really wanted to go, had we had more time, was up into the hills (Alpi Apuane) to the north. Both towns I mentioned, Barga and Castelnuovo, are much smaller than Lucca, remote, and very charming. They are in the hills east of Carrera. constance and her husband could come back to the coast at Piertosanto or just below Carrera, and drive up to La Spezia and Cinque Terre.

Love Lucca and Bergamo. The alta citta in Bergamo has a music conservatory.

Certaldo. Don't tell anyone.

Montecatini

A little further south of Florence, but I loved both Cortona and Volterra, especially Volterra

Borghiditoscana.net Or, for truly undiscovered towns: http://www.borghitalia.it/
Pick your best choice.