I'm traveling this June from Switzerland via the Bernina train to Northern Italy, have two weeks to travel thru Italy and return out of Rome 15 days later. I'm traveling with my husband, 3 teenagers and a 5 year old and we've never been to italy. We thought arrive Tirano train to Milan for 1 night, train to Verona 1 night on way to Venice ( 2 nights) and then rent a car and drove to Tuscany( 5 nights) and Rome ( 5 noghts). I'm having trouble figuring out if this works, can we feasibly drive from venice to Chianti , is Chianti the best town to base in? We want to see Florence, and the hill towns at our leisure. Is cinque terre to far to day trip? Any recs greatly appreciated as well as best towns, accommodations for 6. I'm ok with 300-400 per night for villa or hotel rentals. Thank you!!