Family Trip

Are you planning any time in a mountainous area where it will be cooler? Do you plan to see any ruins like Pompeii? Pompeii will be very hot. It was very hot for us at the end of October. If you are hoping to see Roman ruins, look at going to Ostia Antica as a day trip from Rome, instead of Pompeii. The metro goes right to it, it takes about an hour each way. A lot of it is grass and there are some trees so its cooler. There is a little museum there to get an AC break. Ostia is smaller, has fewer people, but still it has a lot of what Pompeii has, and it will be a much less expensive day..

Have you looked at the itineraries for the Heart of Italy and Best of Venice- Florence- Rome for inspiration?

You could easily do the VFR and just take more days and see more in each location.

What questions do you have? Are you looking for itinerary suggestions outside of the last 5 nights in Rome? Are you locked in to flying RT to Rome, or could you fly into Milan and work your way south?

We rented a villa with pool in the Chianti area of Tuscany for our extended family. It worked out great as we would drive to see other towns during the day and return to the pool and hang out. Our villa was in Panzano and we rented from chianti and more dot com.

Fly into Venice and spend three nights before taking a direct train to Florence (2h 15m). Spend four nights in Florence and visit the Uffizi Gallery and Accademia. You should purchase your Uffizi tickets about two months prior of being there to guarantee your reservations. I would also take a day trip to Siena from Florence (1h 15m bus ride).
From Florence, take a train to Vernazza (Cinque Terre) that will take 3h 30m and requires a connection and sleep in Vernazza three nights to explore the Cinque Terre. From Vernazza you take a train to Rome (4h 30m connection required) and sleep in Rome three nights in the Trastevere neighborhood. Make sure you spend one day in Vatican City.

Wow, you have a lot of time. Here’s a sequence for you. You can, of course, vary it. Venice - 2 - 3 nights arrival; Florence; Siena 1-2 nights, possible 1/2 day bus trip to San Gaminagno (spelling?); Assisi 1-2 nights; Rome.

Or, Venice; Florence; day trip to Siena; Orvieto and civita di bagnoregio; Rome

I second the Ostia Antica recommendation byJules. It will save you a lot of time and, because it is grassy and there are lots of trees, it will be much more comfortable to visit. The Rick Steves Audio Europe app has a great walking tour of the Ostia Antica site so you can avoid having to do much research on the side.

If you go to Venice one unforgettable experience is to take a gondola rowing lesson with Row Venice. You’ll get the chance, once you learn basic rowing, to row out to the Grand Canal. My husband and I did this a few years ago and it is a great memory. They offer lessons in the daytime, at the time for pre-dinner drinks and in the evenings. We did the aperativo lesson and enjoyed rowing up to a canalside bar to enjoy a drink and snack, then rowing to another (the instructor doesn’t drink.). You’ll find Row Venice by googling.

Flying RT Rome.

Backpack, is this in concrete? Before advising itineraries - like into Venice and out of Rome - it would be good to know if this detail is a MUST for your family/budget? It's no issue to work around; just need to know how solid this detail is to your plan.

Thank you for the insightful feedback, all of the suggestions will be looked into and sound amazing! Flights can be changed. We have decided to stay in one place for the entire time this trip. While the Venice Florence Rome suggestion sounds exactly what we’re looking for, what we really want out of this trip is to just relax and be together as a family without worrying about train schedules and check in/out times. We will either stay in Venice or Rome. Any thoughts on which location would be better for a two week stay?

Rome
Stay in Trastevere
https://community.ricksteves.com/travel-forum/italy/is-10-days-in-rome-too-long

How are you with heat? Not that it's guaranteed to be cool in Venice.

If you are staying in only one location - make it Rome/Trastevere, not Venice. It’s not as confined, less expensive, more to see and do, and less of a “theme park” feeling with all the tourists in Venice. Plus with Rome - you can day trip by train to Assisi and Orvieto just to get out for a day. There are probably day trip/guide services as well. You can do a lovely foot tour through Trastevere with Eating Italy. It’s a fun day trying food samples and having a lovely pasta and wine meal as well as some history thrown in. Eating Italy provides local, friendly guides and reasonable prices.

If you stay in Venice, you can take a vaporetti (water bus) at twilight from the train station to San Marco square (or vice vs), or even further out so see the palaces that line the Grand Canal illuminated by their giant crystal chandeliers showing the interior of the foyers. It will take you back in time. You also want to get lost in Venice.
Good day trip options from Venice include Burano (1h 15m), Padua (30-minutes) and you want to reserve tickets before leaving home so you can tour the Scrovegni Chapel and then the old town afterwards. Other day trips are Vicenza (45-minutes) and Verona (1h 15m).
If you stay in Rome sleep in the Trastevere neighborhood and make sure you visit Rome’s oldest square, the Piazza del Popolo. Also make a point of seeing the Colosseum at night, it’s all about the lighting. The food will be better in Rome than Venice too
Day trips from Rome are: Vatican City, Orvieto (1h 15m), Florence (1h 45m) and Naples (1h 15m) and explore the Spanish Quarter.