Help with creating an Italian itinerary

Rome 4 days, Florence and Tuscany (Siena, hill towns) 5 days, Venice 2-3 full days and you are left with 2 to 3 days). Either add a day to each of your must destinations or go to lake Como or Dolomites. Or go to Cinque Terra.

First of all, I think it is doable if you are flexible on budget and flights.
Not knowing ANYTHING about your family's interests and I were planning this trip, I would fly into Venice and out of Rome.

Venice -4 nights
Tuscany - 5nights
Rome- 4 nights.

I would rent a car just for the Tuscany portion of the trip. I would base at an agriturismo between Florence and Siena so as to make day trips to those if desired. I would pick a place with a pool so as to come back in late afternoon for a swim while gazing over the gorgeous Tuscan landscape, and also pick a place that offers the option of meals if you don't feel like going back out for dinner.
this would give you the cities and also a taste of the countryside.
Alternately, if you do not have much interest in the tuscan countryside, base in Florence for the 5 nights and you can do a day trip to Siena or the countryside if you mainly want a city based vacation.
Probably your biggest challenge is finding accomodations for the 6 of you. Are you thinking 2 rooms?

Dianna, a little more info would be helpful? We have no idea what you or your son's interests are. The classic first-timer's trip is Venice, Florence (capital of Tuscany) and Rome but what you DO in any of these places is up in air. For instance, there are tons of fabulous art museums, gorgeous churches and ancient ruins (Rome) but if your young men would find all that desperately boring, then it won't be a good trip. They may be looking for more active pursuits such as hiking and/or beach time.

What sorts of activities/sightseeing would make this a successful endeavor for all?

I might disagree with renting a van (which you would need for 6 people +luggage) if concentrating on cities with just a few day trips. Train travel is very easy in Italy, and gets you from city center to city center much easier than a vehicle. Day trips can often be very easy by rail as well, and your young people may enjoy the novelty not to mention a lesson in how many young people get about Europe: good for future reference!

They should also be actively involved in the planning as if they have a hand in the research and itinerary, there will be little to complain about later. It's another learning opportunity in the fine art of travel. So, don't feel like you should be doing ALL the work here?

Get a couple of guidebooks and start there. Two weeks is not a lot of time for six people, so Kathy's suggestions are very good, especially about transportation and planning. Perhaps have each son plan half a day in each city? Or each pick a day of the trip to plan?

Something to look at that your young men might love (well actually everyone will love it) is the Val Gardena in the Dolomites. Note, you'd have to give something up for this, and I am (horrors!) going to suggest you give up Roma. You have no doubt visited it and your sons will in their lifetime manage to do so but, as a, family you might really enjoy this mountain destination where hiking and biking are such a pleasure and the scenery is incomparable. Note also that this destination will work best for the later dates.

Ideally, fly into Venice (Venezia) and spend 4 nights. Sounds like a long time, but it is really only 3 full days to tour.

Then on to the Val Gardena. I like Ortisei best but look also at Santa Cristina and Selva. Again, 4 nights.

For your remaining nights, (5 or 6?) go to Tuscany. After the big countryside dose of the V.G., you might like to stay in Florence/Firenze and treat yourselves to a couple of escorted day trips (try Tours By Roberto) into the Tuscan landscape for wine tasting or just touring and enjoy a car-free vacation. Fly home out of Firenze.

If you want more info on going car-free or on the Val Gardena, PM me.

Dianna--

It's not overly ambitious, but you have to see what works and what's available only 5 months out. It's doable, however--you just have to get started in short order.

Yes, yes, as Kathy said, get your sons' input first off. Let them read some guidebooks, do some online what-if's in the next few days but don't let it go any longer than that. And they probably won't think about cost--that's your job, and you & hubby will have final veto power.

Initial order of business will be air reservations. Open-jaw is preferable--in one city, out the other. You will be in high season, so plan on following up those reservations immediately with lodging reservations. With six of you, a large apartment in each city venue would be preferable and will save you some money.

Let's assume you have 13 nights on the ground. I would fly into Naples Capodochino, and begin this adventure on the Amalfi Coast. Sorrento or Ravello are great choices for 3-4 nights, a chill way to start off. Maybe find 3 rooms in a B&B, or even an agriturismo. Then a train to Rome--find an apartment through VRBO, HomeAway, etc., for 3-4 nights. You should be fortified from the down time to handle all Rome has to offer. Walk, walk, walk, or tour on the Hop-On-Hop-Off buses, drink in the Eternal City. Then train to Florence, another apartment, wander Florence, maybe a daytrip or two, another 4-5 nights, or possibly find a villa out in the Tuscan countryside. Best to hire a driver/van to be at your disposal if you do this option. Then you can fly out of Florence.

I know Venice isn't in my itinerary but you can daytrip it from Florence, 2 hrs each way by train. I just think that the A.C. is a better choice with the boys. Great hiking, food, spectacular scenery.

This won't be cheap but at least you have the Euro/USD conversion working in your favor--1.09:1 as of Sunday. Enjoy your planning!!

I agree with the others, into Venice, then Florence/Tuscany, and out of Rome. But, I do think the boys would like Cinque Terre. They can hike, go to beaches, there are younger people (especially in Vernazza) with somewhat of a nightlife, so they might welcome the change. But, I don't know their interests...let them help choose!

I definitely agree with Cinque Terra - it's so unique, and you can hike, kayak, sit on the beach, eat delicious food. So much fun. See if you can stay with Giuliano to get some local flavor. http://www.tripadvisor.com/Hotel_Review-g187822-d283494-Reviews-Camere_Giuliano-Vernazza_Cinque_Terre_Italian_Riviera_Liguria.html He has three rooms right next to each other, and it would be a fun place to stay as a family.

It's also a good idea to fly in one city and out another. Everyone that I talk to says that 1-2 days in Venice is MORE than enough. I would consider flying into Milan and out of Rome. Spend 1-2 nights in Venice, 2 nights or so in Rome, 2 nights in CT, and the rest in Florence/Tuscany. You could also consider the Amalfi Coast, which I have never been to, but hear is amazing. You can stay in Florence as a hub and do day trips around Tuscany, or stay somewhere in the countryside.

We did a similar trip in May 2015. We (wife and 2 sons, ages 21 and 25) flew into Rome and out of Venice. We spent 4 nights in Rome (Trastavere), 1 night in the Cinque Terre, 3 nights in Florence (Next door to Medici Chapel) and 3 nights in Venice (Frari Church area). We rented apartments through VRBO/HomeAway in Rome, Florence and Venice. You should be able to find something suitable for your family with them. I highly recommend only looking at properties that have multiple "real life" ratings. We rented 2 bed, 2 bath apartments for 150 to 175 euros per night. Each was in a very nice location. Another option for lodging is booking.com.

We booked train travel ahead of time to save on fares. If you buy far in advance, you can get super economy tickets (ours from Florence to Venice cost 76 euros for the four of us total). With 6 people, you could easily save $150 per leg on trenitalia. You can try trenitalia.com or italotreno.com to compare prices.

For airfare, prices can vary wildly that time of year. I suggest flying into and out of different airports with one exception. The cheapest airfares I have seen recently are into/out of Milan. Check flights.google.com for your preferred travel dates and look at the options. If you can save a lot of $$, I would go with Milan and take the train from there to the other cities upon arrival. The travel time between Milan and Venice (2:30), Florence (1:40) and Rome (2:55) is not bad at all.