Italy- 13/14 days

I'm taking my family to Italy for 12 days in July and friends suggested that it's a good idea to balance out the busy cities, like Rome and Florence, with low-key experiences. So we are doing three nights in Rome, then two nights in Cinque Terre, then two nights in Florence, a night in Tuscany and two nights in Venice before heading back to Rome for one night before for our flight home. You're giving yourself more time in each city, which is awesome. I wish I'd added two more days to our trip, but it's set now and can't be rebooked without a high cost.

We have booked the high-speed train from Venice to Rome. Looks like an awesome way to travel.

As for guides, I'm booking ours in advance for this trip. Last year, my husband and I waited too long to book guides, trying to book them just a month before our trip to Barcelona, France and Italy, and most of the good ones were fully booked and we had to do group tours instead of private tours. Why don't you call your hotel and ask for recommendations now?

Just a few thoughts here:

If you haven't already booked your flights, you need to add a few more days to fit in all the places you want to see and not be running all the time. Also, check the details on the flight home from Venice. Many posters have realized too late that they are departing from Venice extremely early in the morning and will have to wake up at an ungodly hour to make it to the airport on time, sometimes via a costly private transfer. If you can reverse your trip and fly into Venice and out of Naples or Rome, things may well go more smoothly.

Most (admittedly, not all) travelers are sleep-deprived and jetlagged after an overnight transatlantic flight. That first partial day is usually not worth a great deal and gets used for walking around outdoors (trying to adjust to the new time zone), just trying to stay awake. So your planned 2 nights in Naples is really just one day. That seems very short, given your heritage. Whatever you do, do not pay in advance for a guided tour (or, worse, a private guide) on that first day!

I understand the desire for some down-time, but the one place where I think you could cut a night (and reassign it elsewhere) is the Cinque Terre. It's not that 3 nights wouldn't be pleasant there, but 3 nights in CT and just two in Venice and Naples...well, that's not what I would want to do.

It's lovely to spend some time in smaller place like Orvieto and Siena (Civita di Bagnoregio just isn't in the same category for me), but you really don't have time to do that.

I think private guides are usually a nice-to-have (if money isn't tight), not a necessity. But you're traveling in a group of 4 and are trying to squeeze in a lot of destinations. I can see that a private guide would make for more efficient sightseeing. If you find the cost a bit too much to swallow, look into walking tours. They are usually quite inexpensive and can often be taken on the spur of the moment. Rick has some free downloadable walking tours on this website.

Does 2 nights in Naples, 3 nights in Rome, 3 nights in Florence and 3
nights(to relax a bit) in CT and then then 2 nights in Venice sound
good. Can I take side trips from CT ?

Vermount, a schedule this tight doesn't much room for any day trips at all, IMHO. Understand that you are going to lose 1/2 day or more every time you change locations and/or on arrival day so 2 nights in Naples will only give you 1 full, non-jet-lagged day. Figure 2.5 days in Rome, 2.5 days in Florence, 2.5 days in the CT and 1.5 days in Venice. That's not much.

I would also try to avoid flying home from Venice if possible because of the complications with early flights acraven mentioned. I might also cut that one and add a night to Naples and Rome, or cut the CT and add those nights to Naples, Rome and Venice.

We do enjoy train travel and I was thinking of the "Frecciargento" to
take me to Venice from either CT or Florence.

You should take trains between ALL of your destinations but that's a subject for a new thread. :O)

Guides: Personally I don't think those are essential as we've done almost all of our travel in Italy (so far) without them although there are instances - such as the Vatican in Rome - where a tour can save you time and extra footwork. It does mean doing the homework so that you know what it is you are interested in seeing, best ways to get tickets (we can help), making use of audioguides when available, etc. so again, that's a subject that deserves a thread of its own.

prefer to stay in each area a little longer and take side trips

Kathy has given you particularly good insight into the challenges of your plan. It is a very fast past. I think you should drop at least one location. You barely have time to spend in the location much less take side trips.

If Naples is a must do for family reasons, I think I would drop Venice as an outlier.

Naples (3 nights)

Rome (4 nights)

CInque Terre (3 nights)

Florence (3 or 4 nights) and fly out of Florence.

The Frecciargento is just one type of high-speed train. The Frecciarossa is the highest speed train and should be your choice when it is available.

Have you been to Italy before? I would guess no and say that I find your schedule not one where you will be doing much relaxing. Sorry.
You will land in Naples. I've only been there as a quick stop to Sorrento so have no thoughts about this area. However, from what has been written on the Forum about Naples, it is a "grittier" city and personally, not one in which I would want to spend my first few nights in Italy. If it is important to you, then go. But if you can forgo Naples, then add one night each to Rome and Venice or Florence. I would not go to more than 3-4 places max in the amount of time you have. I much prefer Florence and Venice over Rome, but that is my preference.

Alternate suggestions:
Fly into Rome (4 nights)
Train to Venice (3 nights) or skip and do CT
Train to Florence (4 nights)
Train to Milan (2 nights) fly out of Milan
or
Fly into Florence (5 nights)
Train to Venice or skip and do CT (3 nights)
Train to Rome (5 nights)

You could easily do day trips from Florence and Rome to other areas.I don't think you need a personal tour guide but I would definitely take walking tours in each city. There are tons to choose from. Check the RS books for suggestions or go to the city website. Bottom line is what you and your kids want to do and see. Have you asked them? Regardless of what you finally decide to do, I am sure you will have a great trip!

I was thinking about this a little more this morning and will offer up yet another suggestion?

(We) prefer to stay in each area a little longer and take side trips.

Can I take side trips from CT ? Or would it be better to visit some
towns in route to CT.

If this is the goal, I'd consider dropping the CT as well as Venice. The CT is not a great location for day trips other than just exploring the immediate area (the 5 villages plus maybe Porto Venere). Florence, on the other hand, offers much more efficient public transit access to, say, Siena and Lucca. Those day trips, IMHO, are easier when not having to deal with luggage so it's a very good base for a longer stay...not to mention it's a goldmine of Renaissance art, which is something you mention having strong interest in.

Orvietto is best done as a day trip from Rome, and the Eternal City offers SO much to see all by itself that again, you could make it another base for the longer stay you desire. We spent 6 nights there on our 2nd trip (my 3rd) without coming close to running out of things to do.

One more benefit for fewer locations/longer stays? You can more easily flex with the weather, attraction closures or any other little snags travel can throw you. The CT, for example, doesn't have much to do when it rains whereas Florence and Rome offer many more indoor opportunities. Need a little down time to relax? Longer stays make that more possible as you don't feel you have to use every precious minute rushing to get all the must-sees done!

If your principal interest in going to Naples is cooking of the region, you could consider staying somewhere in Campania near Naples rather than in Naples itself. I have not spent any time in Naples, but as was noted up-thread, there are plenty of people who have actively disliked their visits. What about staying in Salerno instead? It's a medium sized city about an hour south of Naples by train. It's a pretty place, right on the coast, and day trips to lots of places would be easy from there. I had one of the best meals of many in a lengthy trip to Italy at a restaurant near the train station there. If you're traveling with an Art Major, it would be a shame to skip Venice. I know Art Major will likely have return visits to Italy in the future, but the art in Venice is absolutely fabulous. If I were booking this trip, I would do north to south, with 3 nights in Venice, 3 nights in Florence, 3 or 4 nights in Salerno and 3 or 4 nights in Rome. This involves some back-tracking, I know, but you could have the down time you're looking for in Salerno instead of CT (think ferry boat rides along the Amalfi Coast, a trip to the beach). If you can afford a private guide in each city for a day, I would book them. Certainly they are not necessary, but the few I booked on my lengthy trip were among the highlights of the trip, and if I had it to do again, I would have splurged on more of them. I think they will be particularly valuable for your kids.

Here is my path since you want to flying into Naples and out of Venice.
Note if you have not booked flights, try to book a late morning flight out of Venice.

4N Naples

Alibus into Naples 15 min. If staying in Sorrento, Curreri Viaggi bus 1H15 min
Both of these are outside the arrivals terminal.

Do some research on the town your grandmother came from.
If you plan to visit.

3N Rome. Train 1H15 min.

3N Florence. Train 90 min.

3 N Venice. Train 2H05 min

All you wanted to know about Venice.
http://europeforvisitors.com/venice/index.html

Given the total number of nights you listed, I would suggest adding one more in Rome and Venice and skip CT

CT is probably the least day trip friendly location you have listed.

If you want to give yourself a "break", make one day in Florence an open/unscheduled day.

An RS tour can move every couple of days as they use a dedicated charter bus to take one directly from point to point, a luxury the independent traveler using trains does not have.

Some times less is better ( i.e. fewer stops with all the unpacking/packing etc)