Itinerary help…day trips or new lodging??

Hi Sarah, welcome to the RS forums!

Quick initial thoughts...
Venice and Siena are too far away to day-trip from Rome. Florence is a lovely (but busy) city with a compact, nicely walkable historical center which offers a LOT to see if you're interested in Renaissance art & architecture. This is where you should base if wishing to day-trip both Siena and Venice. That said, fans of Venice will vote for staying there for at least a couple of nights.

I'd base in Rome for Pompeii, Orvieto and maybe Assisi, and Florence for Venice and Siena. There are other good day-trips from that latter city as well. You do not need or even want a car in any of these locations: train should be your mode of transport other than maybe bus from Florence> Siena as it drops you off closer to the city's center.

You might consider going directly to Florence upon arrival in Rome and then changing bases, as you'll be flying out of Fiumicino (I'm assuming,) One question about this?

We have free lodging in Rome (a friend lives in a villa there)

Do you have an address or otherwise know exactly where this residence is? Rome encompasses a very large area, and I'm concerned just how far out of the historic center your friend lives.

If you need to stay at the friend's villa at the start of the trip, so be it. But, if not, I agree with Kathy about going directly to Florence, Venice, and then back to Rome. Of course you could go straight to Venice which is a wonderful place to recove from jet lag and get acclimated to a new world, and then Florence. I would not stay overnight in Assisi. Trains are the way to go -- no worries about speed cameras, parking or ZTL areas. Once you get the order of your stays settled, then work on what can be done on day trips.

Sounds like a wonderful trip! I am assuming 2 weeks includes travel so that really gives you 11 1/2 days.

I think Pompei is wonderful, especially with teens, but I think it is the outlier and I would let it go. Where do your teens want to go and what is their travel personality? Get up and go or sleeping in? Loves museums? More outdoorsy? Shopping? Food lovers?

I am not a huge fan of too much day tripping. You arrive with all of the crowds of the other day trippers, I would rather be there for the quiet mornings and evenings. You end up doing so much backtracking, and I am always so weary at the end of the day. And train tickets start adding up especially x4. Also, you don't all have to be so glued at the hip if someone wants to go back to the room to take a break or constantly watching the time to catch the train.

I could see landing in Rome, immediately flying to Venice for a 3 night stay, train to Florence for a 2 night stay, pick up a car and head to Siena or Mulipulciano for a 2 night stay, finish your list on the way to Rome, then return the in the car in Rome and finishing your trip there. The car gives you so much flexibility in Tuscany and with a little research, the ZTLs were very easy to avoid. Enjoy!

Orvieto and possibly Pompeii can be visited on a day trip from Rome. Assisi is kind of a long stretch. Florence has too much to see to be visited on a day trip, although only 90 min away by high speed train. Siena is not easy to reach from Rome, but it’s an easy day trip from Florence.
Venice is too far north for a day trip.

You could fly on an open jaw, multi- city ticket, so you don't have to waste a day backtracking.
Perhaps fly into Venice (or Milan),
Train to Florence ( day trips to Tuscany)
Then Rome.
I suggest this, as opposed to the reverse, as Venice can be hard to fly out of. I was unclear on whether the plane tickets have already been purchased ?
How many nights will you actually have? It's more functional to count by nights, than days.
You have so many choices, but note that the group moves as fast as the slowest member. Are your teens morning folks? If not, constant day tripping, with early start times, can become exhausting for all. Having unplanned days can be a gift, especially in Venice and Florence , where the teens could wander by themselves.
Whatever you decided, you'll have a wonderful family trip.
Safe travels!

I guess that is an outstanding question: have you purchased your plane tickets yet? If not, flying into Venice and out of Rome would save some backtracking. Maybe an itinerary like...
Venice - 3 nights
Florence - 5-6 nights/2-3 day trips
Rome - 5-6 nights/2 day trips

Only do a day trip if one way is less than 1/5 hrs

Thank you all for your feedback. Unfortunately, plane tickets were already purchased before we mapped out our trip. I can see now that it would have been better to fly into one city and out of another to avoid backtracking. But alas, we will make the most of it and do better next time.

My teens want to sightsee! They will be fine getting up early, but don’t want to be so rushed that it feels hectic. They haven’t been out of the country but when we visited the national parks, it was common for us to get up at 5am and go all day!

We have 13 nights total and are now thinking we will do fewer day trips so we can spend less time traveling and enjoy morning/evenings with fewer crowds. Plus train tickets for 4 will pretty much cover room cost. Thoughts on this plan…
Rome (3 nights)
Assisi (1 night)
Florence (4 nights w/ day trip to Siena)
Venice (2 nights)
Rome (3 nights w/ possible day trip to Pompeii)

I actually like the idea of splitting up our time in Rome since the crowds might be really crazy with the Jubilee. And there are so many churches that it might be nice to take a break from that?? Maybe I’m just trying to make myself feel better about having to backtrack!!

It sounds like your kids are troopers and a delight to travel with!

Unless your traveling day to Rome already will have a long drive, flight connections or long airport waits, I would really consider catching a flight from Rome to Venice on the first day, soon after landing. Then you can work your way down.

The train from Venice to Florence is easy. Then, if you got a car to get to Assisi and add another night there, you could visit a few other Tuscan towns along the way. Day tripping from Florence is fine but the hotel prices in Assisi are probably more reasonable. I like doing Rome at the end all together. There are many areas in Rome to escape the crowds and a day trip to Pompei could break it up.

I agree with last post, fly from FCO to Venice and work your way back to Rome. I personally dread navigating from FCO into Rome, luggage, train, Uber whatever you do it’s time-consuming and usually expensive. I would prefer only doing it once on a trip.

You have scheduled Assisi for one night and Venice for two nights. Two nights only gives you one full day and parts of the arrival and departure days for Venice; one of the most unique places in Europe. You might want to consider not staying in Assisi and using that night for Venice. Just food for thought.

Venice (2 nights)