Second guessing Itinerary for family of 4

Looks a bit busy to me but you do say that your family is pretty active. I do, however, question time and activities in the Cinque Terre. I'd be concerned about the temperature for any of your activities. You don't say what your arrival time is in Rome. If it's early in the morning you might be surprised by how much time you'll have. I'd suggest walking around and seeing from the outside the places you want to go into. Of course, there's much to do outside too like Piazza Navona, Trevi Fountain, Piazza San Pietro, not to mention lots of streets to meander through. Two nights in Venice? Could you cut CT and give that time to Rome and Venice?

You are going to get lots of ideas on this site. Enjoy your planning and enjoy your trip! You can start planning the next trip on the plane heading home.

Unfortunately to answer your questions just generates more questions…
Is this your family’s first trip to Europe or Italy?
Your family is active but are you interested in the artistic and culinary things that are booked, or are some of them scheduled because they are things you are “supposed to do” in Italy?

Evaluate these questions honestly because you know your family best and can then make the best decisions.

FWIW—our family of 4 took our first trip to Europe last year. Our 2 “kids” were 20 and 22; so not teenagers. Except for our first night we stayed at every hotel at least 3 nights. There were some days where we stayed longer (like Florence and Rome), where didn’t have anything planned and just “roamed.” Frankly, we didn’t go the Accademia and we were okay with that. While our family really enjoyed the trip, everyone from kids to spouse said they wished we had spent more time in fewer places. We used this trip to essentially plan our next trip…—go back to see that—skip this, etc.

So, based on our experience, if I were to give any “definitive” suggestion it would be to avoid staying anywhere less than 3 nights. Keep that in mind when committing to your schedule (or schedule change). Travel days, even with high speed trains, greatly limited your ability to accomplish anything other than moving that day.

That's a lot of moving around. You're proposing to visit 3 great and important European cities. Remember your first and last days are essentially wasted and every time you change cities you lose a day. You may not have time to see the C/T this trip.

Fly into Rome and spend 4 nights. Take a train to Florence.

Spend 3 nights in Florence. Take an organized tour out of there around Tuscany. I like to visit Siena, San Gimignano, Volterra and possibly one of the wine towns like Montalcino. Take a train to Venice.

Spend the remainder of your time in Venice and you'll fly out of there to another European gateway city.

I have traveled with two 20 somethings on a similar itinerary with some slight modifications (we rented a car in Florence and then stayed at a B&B outside Siena. A couple of thoughts. I prefer your option 1. Remember every time you change locations, you will eat up 1/2 day in transfer time.

• Driving. It was relatively easy to drive in Italy. However, picking up a car, dropping it off takes away from valuable site seeing time. You do not need a car in Siena and it is a pain in the but to park in Siena, especially if you are going on market day. If you drive, you will also need an International Drivers License--easy to get before you leave.
• CT. This was by far the most favorite of my 20 somethings. However, we went in mid-May and had a lot of rain, so hiking was not great. The one day we were scheduled to go on a sunset boat ride, the weather was very choppy and they cancelled all but the ferries. We were lucky to talk one of the owners going out on a two-hour ride. It was choppy, but nothing really bad for a San Francisco Bay girl. If you are going to the CT to hike and kayak, then April weather can be a bit iffy.
• Train from CT to Venice: this will take you about 5 hours, so you really don't have a lot of time in Venice, not even a half day unless you leave early from the CT.

A couple of thoughts from my experience. Plot out all the travel times for each of your options and then determine whether you really want to go to CT and/or Tuscany or do you want to apply that time to either Venice or Rome. At the end of our trip, everyone agreed that we would have been better off slowing down just a bit. If you are happy with the pace, then look at this as you will get a taste of each location to determine which one you want to go back to in the future to explore more.

I don't have teenagers, but we have done a lot of traveling with our kiddo (now 6), and as a party of five (four adults and one kiddo). For me, there is a difference between not having a lot of downtime (which I totally understand, as that's my travel style), and spending a lot of time moving between destinations.

As others have pointed out, moving overnight locations is a lot of work and time, much more so than just physically getting from destination to destination. There's packing, checking out, hauling your stuff to the train station, traveling to a new city, checking into a new hotel, unpacking, etc. How independent and self-sufficient are your teenagers? Will they be able to reliably pack and unpack and not leave things behind in a hotel room or apartment? No judgment either way - I can't trust my 35 year old husband to do that :) - but it is something to think about. The more moving you do, the more likely things will be left behind.

If it were me, I'd cut out CT and allocate one extra night to Florence and one extra night to Venice.

The 'alternative' itinerary has one more sleeping location than the 'current' version. For that reason I like the 'current' version better. It is a busy trip, no need to make it busier.

Curious-- where does the flight that leaves Venice past 6PM go?

We are a family of 5 (3 adult children) and have roughly the same schedule. 3 nights in Rome, 2 nights in CT, 2 nights in Florence and 3 nights in Venice (we leave early morning the third day). We are also a very active family and don’t mind a packed schedule. Honestly, with the cost for 5 of us, I’m not sure we will be going back too often so I wanted to at least get a taste of these place rather than not see them at all. 🤷🏼‍♀️