Taking a 2 week cruise departing and returning to Venice, Italy next September. Would like to plan an extra 1.5- 2 weeks in Italy (already been to Rome, Florence, Naples, Venice, Tuscany). Haven't made flight reservations yet but we'll be using FF miles for one round trip ticket and paying for the other one. This is what I'm thinking:
Option 1: Fly RT to/from Milan and spend a couple of days there. Train it to Bologna for a couple of days and onto Venice for a few days until we take our cruise. After cruise, rent a car and drive to Verona from where we can spend at least a week or more doing day trips. Drive to Milan, drop car off and fly back home.
Or......
Option 2: Fly RT to/from Rome and take the train straight to Florence (been to Rome a few times and Florence only once). Spend 2-3 days in Florence and train it to Bologna for a couple of days and onto Venice for a few days before we depart for our cruise. After the cruise, rent a car and drive to Ravenna, onto San Marino, onto Assisi and finally back to Rome for our flight back. Not sure how long we'll spend in Ravenna, San Marino and Assisi yet. I know this route is more stops than the other option, but right now the flights for Milan are more expensive and not very direct and flying into Florence is not much better....and into Venice it's even worse.
I won't be able to make our RT reservations until 11/10, so I still have a little time to play around with this.
I've made a list of all the day trips we can do from each place and we don't want to drive more than an hour to each day trip.
I would appreciate any suggestions, advice or input on this.