I used to live in Italy before moving to London a few years ago. My husband is from Italy so we were there for a number of years before moving over.
If you're staying primarily in Tuscany, I would suggest Volterra. Many people overlook Volterra when in fact it is more beautiful than San Gimignano, and a nicer & smaller version of Siena. Volterra offers lovely slow food eateries throughout and a great Gelateria Caffetteria called
Chic e Shock. Children love it and adults do too! (
http://www.vigilucci.it)
The views from the old fortress of Volterra (now a prison) over the Tuscan landscape is untouched and frankly breathtaking, one of the best. One church in Volterra even holds a Caravaggio and there are various museums too. It is a beautiful medieval town.
Check this out: (I am a fan of Rick Steve's reports)
http://www.ricksteves.com/watch-read-li ... dolce-vita
If you want further sight-seeing or reliable food suggestions my friend, Annie Adair, runs Tuscan Tour (
http://www.tuscantour.com). Tuscan Tour is a wedding and touring operation that Annie runs her home right outside the walls of Volterra, and she is married to a local. If you pop her an email she can make you some fabulous and well-known local restaurants and places for you and your family.
I would not suggest Cinque Terre to be honest because the main walking areas of Cinque Terre have not fully recouped since the landslides of a couple of years ago. We have a place near there, closer to Nervi, but we check in periodically and many of the walks are still inaccessible.
A lovely town to visit is Massimo Maritima. It's higher in the hills. An alternative, yet great place to relax and have a picnic lunch, should you want to go for a countryside drive in southern Tuscany, is Manciano. Right outside Manciano, there is a natural thermal spring that has created a small lagoon with low running currents that run over flat rocks. Many locals enjoy it there and have picnics. There are picnic tables set up and parking is nearby.
Depends what you'd like to do with the children, but if the weather permits at that time, it might be nice.
(
http://www.tuscanypass.com/tuscany_ther ... urnia.html)
I have other suggestions, but don't want to bombard you. If you want to PM me, feel free. While I lived in Italy, and still go back because we have a place there, we traveled a lot all over.
No matter where you go, what you do, make sure you choose your places to eat based on reviews. Touristy places to eat in Italy are always disgusting and disappointing. TripAdvisor is great for restaurant reviews in Italy - even Italians review places.
Eating good food MUST be a key requirement to any holiday organised in Italy
Buon viaggio...
Mrs.AAA