My fiancée and I are planning to go to Italy in mid to late-May 2020 for 11 days and 10 nights (with the possibility of extending the trip by a couple of days). We're considering all options but are thinking of flying from JFK into Venice and leaving from Milan. We'd like to focus on the northern half of Italy and perhaps go as far south as the Tuscany area.
We've done enough traveling in Europe now that each of us only takes a carry-on bag and a backpack - so mobility won't be too much of an issue. I've read about driving in Italy and am thinking of only renting a car in the Tuscany area, otherwise we plan on mostly train travel. So...
Day 1: arrive in Venice by noon
Day 2: Venice
Day 3: Venice and take train to Florence
Day 4: Florence
Day 5: rent car to drive into Tuscany area
Day 6: Tuscany
Day 7: Tuscany
Day 8: return car and take train to either Cinque Terre or Lake Como area
Day 9: Cinque Terre or Lake Como
Day 10: Cinque Terre or Lake Como, travel to hotel near Milan Airport for overnight before morning flight on day 11
Day 11: depart from Milan at 10am
As I said, we have the option of extending the trip by a couple of days, still working on that. But does this timeframe seem doable?