I have just started reading this message board and am so impressed with how friendly and willing you are to share experience and advice. I thought I would ask for your guidance.
I am planning a trip to Italy in June with my 2 teenage daughters and my husband. We have the basics planned and I am looking for suggestions on sights and best way to travel from one place to another.
We fly into Rome for 4 nights. We are staying at the Grand Plaza Hotel near the Spanish Steps. Our plans are to see see the usual sights Forum, Vatican, Pantheon and have one day trip probably to Tivoli.
We travel to Positano but uncertain the best way to travel there. We stay 2 nights at the Covo Dei Saraceni. Pompeii is on our list of places to see and possibly Capri.
We travel to Siena for 1 night at a winery and 2 nights at the Palasso Ravizza in Siena. I would like to take one day trip to Florence.
Then we travel to Venice for 3 nights at the Hotel Londra.
From Venice we go to Milan for 2 nights staying at the Hermitage Hotel.
Any suggestions or tips would be greatly appreciated. Thank you.

I am one of several people who have fewer positive things to say about the Grand Plaza than negative. It is resting on laurels of yesteryear. You can find better and pay less.

Best wishes,

Rex

Dear Joni:

You may want to repost your message with a more specfic title, not so general. Such as: Trip to Italy with teenagers. Use something to call attention to Italy and your kids.

Do you have a guide book. If this is your first trip to Italy, I recommend Rick Steve's Italy. Steps you through everything and offers good info on getting from place to place.

Good luck,
Michelle

No one has responded to your concern for getting from one place to another... You are covering a lot of territory in a short amount of time with four people. I assume you've made your flight arrangements and are locked into arrive Rome, depart Milan. For your visit flying into Naples, doing Positano, then working your way north to Rome, Siena, Venice, and Milan might have been better. You are changing hotels 6 times in 14 nights. Yikes! Certainly, aside from your stops in Tuscany, your remaining itinerary could be accomplished easily by train. You must weigh the cost of four sets tickets against costs of car rental and fuel.

The big question for me would be, does someone in your family want to do any driving and how much? Some find driving in Italy a challenge and Amalfi coast driving
particularly scary.

You might visit Rome, then take the train to Positano. Finished in Positano, pick up car in Naples and drive to Siena. Keep car in Siena, then drive to Venice. Turn in car in Venice. Take train to Milan.

You must think about what YOU would like to do.

I agree with the previous poster's suggestions on when to drive vs. when to train. Having a car is preferable in Tuscany, so you can drive from hill town to hill town. Having a car is a major hassle in Rome or Venice. I've only driven as far south as Sorrento; I know I'd be very stressed driving on the narrow cliff roads of the Amalfi coast.

Unless there's something you really want to see in Milan, I'd cut back to one night there, and add that night to Siena. (I'd probably have stayed in Florence, but Siena's a great place to stay as well.)

The campo in Siena is a great place to people-watch. The restaurants that ring it are over-priced, but if you have a nice pizza lunch at one of those restaurants, you can view the higher prices the costs of such a good location!