Rome, Tuscany and Capri - all in 11 days?

Personally, I would do a day trip to Capri as opposed to three days. I found it very scenic but otherwise not terribly interesting. One day was fine, maybe one night but that would be it. Add those days to Positano and might skip one night in Naples and add to Rome. CT is too far in the wrong direction.

I think either works since you are going both north and south of Rome. Just depends on if you want relaxing in Tuscany first or the busy-ness of Rome first.
Train to Salerno works well if you are going to Amalfi coast- Positano- but not so well to Capri.

Since you want a night in Naples as well- I think I would do train to Salerno- ferry to Positano 2 nights- then ferry to Capri 2 nights- ferry to Naples 1 night, train to Rome.
But you certainly could do the opposite-
train to Naples 1 night- ferry to Capri 2 nights, Positano 2 nights then ferry to Salerno for train back to Rome.

Or you could spend all your days in Sorrento and day trip to Positano, Capri, Pompeii, Naples. We did a day trip to Capri and that was enough for us. A few hours in Positano was also enough. We stayed in Sorrento 4 nights, Amalfi/Ravello 3 nights then Salerno 2 nights to see Paestum.

Will you have a car in Tuscany? If so then Montepulciano cannot be beat- we loved it there but you'd want/need a car if you want to tour around Tuscany from there. Pienza is also lovely we are staying there this next trip.
If no car then Siena is probably best.

Haven't been to CT and not really interested- the crowds are a real turn off to me. Amalfi will be crowded as well but you can escape some of that on Capri.

Thanks! very helpful. I think that's a great idea, regarding the ferries and order of Capri and Positano. I was counting on a night in Naples if we wanted to see Pompeii, and given that our flight is not until 6pm, I didn't feel it necessary to spend the final night in Rome. The idea of base in Sorrento for 4 nights is very appealing. I have a strong recommendation from a friend that we need to do a boat ride around Capri and to the blue grotto, so I didn't think that was reasonable for a day-trip, but please help me with ideas on this one!

Do you recommend 2 nights Rome / 4 nights Tuscany or 3 and 3 each? I don't feel like I have to do ALL of Rome, just the highlights. I will send my kids back for graduation trips to hit every last tourist spot that I covered 30 years ago.

I definitely want to have a car in Tuscany, though I also want to do bike rides.

Also one aspect I am struggling with is, do I rent the car in and out of Rome (to drive to Tuscany) or do I take the fast train to Florence and then rent a car?? Which is faster/easier?

Depends where in Tuscany you are going
Not wise to pick up car on arrival and drive that day to anywhere so you’d have to settle on itinerary first

You can pick up in Siena or Florence

Train to Siena stay 1 night
Pick up car for Tuscany days then drop in Florence

You mentioned riding bikes
Take a look at Lucca-you can ride around the wall there

Based on all my research, I believe that Val d'Orcia is where I would like to stay in Tuscany - and do a day trip to Siena. Taking the fast train to Florence and renting a car in the middle of the city - that seems nuts. But it also seems crazy to drive all the way in and out of Rome. Help needed!

Provided it's not advisable to go from Rome to Tuscany on the arrival day, this would be the likely itinerary:

June 11: arrive Rome at 8am
3 nights Rome (or 2)
* travel to Tuscany (how? where to rent car?) *
3 nights Tuscany (or 4) - Montepulciano, Pienza or Montalcino area
* return car (where??), fast train to Salerno, ferry to Positano *
2 nights Positano and 2 nights Capri, or 4 nights Sorrento
1 night Naples (stop in Pompeii)
June 22: depart Rome at 6pm

claire-

You have 11 nights. Do you really want to change locations 4 or 5 times?
3 would be about right, 4 only if necessary.

We did a day trip to Capri from Sorrento, and I wished we had stayed for a night. However, I think 2 nights is overkill. If you stay in Sorrento, Pompeii is an easy day trip, so you could eliminate your single-nighter in Naples. Also, you might find that a day trip is sufficient for Positano. We went from our Amalfi base; and after lunch we had seen enough, mostly shops selling souvenirs and high-priced clothing. BTW, to fill out our day, we took the Emerald Grotto tour. DON’T! It’s probably the worst tourist trap I’ve ever experienced. Some of the descriptions I’ve read of the Blue Grotto include the same negative aspects of the Green, so we skipped that. If you are thinking of doing the Blue, I strongly suggest you read some of the comments about it posted on this site.

We stayed in Montepulciano and loved it. Visited Montalcino as a day trip and it was just OK to us.
Visited Pienza as a day trip and liked it so much we are staying there in Sept.
It’s very charming, flat hill town with gorgeous views.

There are lots of nice looking agriturismos around Pienza/Montepulciano/San Quirico. I think teens would like the space of a farm stay. And you can never go wrong with a pool!

booking .com has several agriturismo listings.

Check your options for car rental locations on www.autoeurope.com

Chiusi, Siena, Florence…if you need an automatic- Florence might be your best bet. You will also need to make sure car is big enough for all of you and your luggage.

Even with your late 6pm departure flight from Rome I would want to be in Rome night before departure. Too many things can go wrong.

With just 11 nights and the desire for a “real vacation” you might want to think about fewer location changes- fewer 1 or 2 night stays. A 2 night stay is just 1.5 days- minus the time it takes to get there.

Maybe this?

Arrive Rome- 8 am-
train to Naples- Circumvesuviana to Sorrento
Sorrento 4 nights- day trips to Capri, Positano, Naples/Pompeii
Sorrento is a nice town, beautiful views, easy entry to Italy, enough to keep teens interested in the evenings, good for just walking around. Sorrento is a really good base- very easy to get to Capri, Pompeii, Naples and Positano. Bus or ferry
Getting to and around the Amalfi coast is very time consuming.

train Sorrento-Naples-Chiusi via Rome 4.5 hrs
Rent car in Chiusi- (check open/close days/hours)
Drive to your Tuscany destination- 4 nights
day trip to Siena and wherever else.

Drop car in Chiusi- 2 hr train to Rome
Rome 3 nights (plus am of your last day- head to airport about 2)

Rome minimum would be 4 nights to me- but I get the impression you are more interested in Tuscany/Amalfi

Christine, I find your 4/4/3 itinerary very appealing! I can understand why Rome would have to be last instead of first, in order to guarantee we are in Rome on our departing day (6pm departure notwithstanding). Also when we land at 8am on June 11, we will have had only a few hours of sleep (flying from Boston), and some further nap time on a train could be beneficial before we reach our first destination. I am only curious why the choice of Sorrento over Tuscany for the first destination? is it because we wouldn't need to rent a car and drive w/ the jet lag? I kind of have it in my mind that I want to do the countryside before the ocean, but I can be swayed.

Thank you for reaffirming my conviction about staying in the Montepulciano - Pienza area. I will stick with those. It seems like we definitely need to see Siena for a day trip, I am looking forward to that. And if we are there 4 nights we could also see San Gimignano and Monteriggioni. (Unless you can hit an overkill of medieval hill towns)

I understand 3 locales is a lot in 11 days. I wish we had more time. I have already decided that Florence has to be skipped this time. As for Rome, since I've seen all the major sights already, it's really just about enjoying the opportunity to take the kids to amazing historical places for their first time. I definitely acknowledge they'll need to return to Italy again in order to see more things...

is it because we wouldn't need to rent a car and drive w/ the jet lag?

Yes.
I think Tuscany is more relaxing than Sorrento- which is more relaxing than Rome.
Start with the mid intensity- yet not so difficult, move to the low intensity to chill out then on to Rome, the most intense.

3 locales in 11 nights is fine. You just have to try to spend more time IN those 3 locales than time getting to those locales to make the best use of the time you have.