First timer to Italy help!

Did you already set the itinerary and bought the air tickets? For a first timer, based on the places you want to see I would buy a multi-city open jaw ticket and do the following: Fly to Venice VENICE (2 - 3 nights) Train to Florence FLORENCE (2-3 nights in the city) Rent a car and get out of Florence (Florence is not car friendly) REST OF TUSCANY & possibly UMBRIA (2-6 nights in some smaller town or farmhouse) CINQUE TERRE (2-3 nights, better by train after returning car in La Spezia) Train to Rome
ROME (3-4 nights) fly home. Forget Milan and Genoa. Those cities are aesthetically unfit to belong to Italy.

Unfit to belong to Italy???? That's funny... but when I compare those two locations to the rest of Italy I have to say I agree. I ended up in Milan due to plane cancellation and have to admit I had a good time, but would NEVER trade it for any of the other locations that are listed. You plan makes great sense for first timers.
Your trip is this spring? As in now? You probably better get busy on some reservations for that many people. Have a wonderful trip.

Roberto's suggestions are good, but if it turns out that you fly into Milano you could visit the Duomo and Castello Sforzesco, and if any in your group are interested in art, there's Leonardo's Last Supper and the Brera Gallery. You can take an elevator to the roof of the Duomo and see Italy from there.

Skip Milan. Is there something you must see there? Stay in the Cinque Terre so that you can also skip Genoa. Both Genoa and Milan are deeper dives than you need for your first trip to Italy. Do them on your fifth. Lucca is great, but not ideal for wineries or Florence by car. Florence you can get to by train. Lucca is a destination to its own. With a car, I'd suggest finding an agriturismo farther south. Good luck!

I suggest that you skip Milan and Genoa and even Lucca. No significant wineries althrough the CT has its own distinct grapes and wine. From Rome, go one hour north by train to Orvieto and rent your car there. Drive and tour Tuscany with your rental car. Stay in Siena or a nearby Agriturismo. Turn in your rental car at the Siena train station and take the train to Florence. For your 3 sons, all they have to do is stand on the corners in many neighborhoods and watch the seriously cute young Italian girls whiz by on their motor scooters. From Florence, take the train to the CT. You will stop or change trains at Pisa. You may want to see the leaning tower. Nothing else to see in Pisa. From the CT take the 5.5hr train ride to Venice.

Linda, The others have provided some great suggestions, and I agree with the consensus - skip Genoa, Milan and Lucca, as there are other more interesting and scenic areas to see. A couple of questions: > What is the time frame of this trip? > Have you already purchased air tickets? Are they return tickets to Rome? > Have you got hotels booked anywhere? As your trip is "this spring", you'll need to get some arrangements in place very quickly. As this is a "once in a lifetime trip", good planning will ensure that it goes well. Regarding your plans to rent a car, there are a few "caveats" to be aware of. EACH driver will need the compulsory International Driver's Permit, and you'll have to be VERY careful to avoid the Zona Traffico Limitato areas, as steep fines will result for any violations. There are also some potentially expensive "caveats" when using public transport in Italy. When riding Regionale trains, tickets must be validated prior to boarding the train on the day of travel, or hefty fines may result, which will be collected on the spot! When riding the Freccia or other premium trains, reservations are compulsory, and those caught without valid reservations will be (you guessed it), fined on the spot! Tickets must also be validated when riding transit in Rome and other places. If you haven't already bought a copy, I would highly recommend packing along a copy of the Italy 2013 Guidebook, as it provides a lot of good information on hotels, sightseeing, restaurants, etc. Finally, if you're planning to stay in the Cinque Terre, it would be a REALLY good idea to get some accommodations booked SOON! Happy travels!