Rome, Orvieto Sorrento - Itinerary and now considering hiring private driver

Do you have medical equipment or some reason you cannot manage just a carryon? The vast majority of other travelers do it. You just do laundry, easy peasy.
I’m no stranger to splurging now and then, but I cannot fathom this kind of expenditure for something one can so easily do for so much less.
I do believe guides and drivers are classified complete differently, they don’t do both. Also, make sure you are comparing apples to apples as the tour covers other things.

Remember that the choice is not between "carry-on only" and "enormous checked bag." I went carry-on only for many years, but now need to check a bag. I use a 25" Travelpro Maxlite spinner and it is plenty big. I resisted getting a spinner until this bag, but I have to admit it is easier. It goes on trains just fine.

Like Nancy we use the 25” Travelpro spinner. Our carry on days are long past. And I don’t feel guilty about that at all.

As we’ve aged we have found that sometimes we need to throw a bit of money at transportation just to make our travel simpler/doable. We have driven many times in Italy and elsewhere but husband has decided he really doesn’t want to drive anymore.

However 10k for a week of driver/hotels seems extremely high.

Looking at your itinerary I would consider a driver just for the Sicily segment.

To simplify the whole itinerary just do a day trip to Orvieto and return to Rome- from there you can get a direct fast train to Naples. Staying in Naples is just easier overall than the trek to/from Sorrento.

Take a taxi to the airport for your flight to Palermo (I assume?)- have your hotel arrange it

Once in Sicily use a driver from Palermo to Agrigento
Then from Agrigento to your stops on east coast.

United flies direct to EWR from Palermo- seasonal so not sure if thru October- they fly to PMO on Sun, Wed, home from PMO on Thursday, Mon.

Take a look at daytrip.com. You can see now what the cost for a driver to your various locations will be. You can do direct transfers or transfers with stops on the way
https://daytrip.com

We are planning a trip to Sicily- and are using a daytrip.com driver to take us where we need to go.
Total cost for 4 transfers is about $1600

I seriously don't think we can travel with just 2 carry on luggage.
Any suggestion would be appreciated.

Same as some have posted above, we travel for 3 weeks with carryons + 24" checked bags, There's no reason to feel like you MUST travel with carryons only. As well, I don't think you need a driver for MOST of your itinerary if willing to use economical public transport, which many of us do/have done without issue. As well, most of us book our own hotels; a search of the forums will turn up suggestions for your locations.

As I was discussing this with someone who travels extensively in
Italy, he suggested using a driver he hires.

I'm having a bit of an issue with someone who claims to have traveled extensively in Italy recommending a $10,000-a-week driver + hoteI reservation service unless they travel at a luxury level most of us here do not. No problem with a different style but it's over-and-above what most of us would expend. Public transport is generally economical and efficient, and we personally prefer to book our own accommodations so we've never used a service such as you're considering. To highlight what someone else mentioned, there's a difference between a driver and a guide: they are rarely one and the same due to Italy's strict licensing rules for guides. Do you have mobility issues that makes a driver mandatory for this trip?

As suggested, maybe consider using a driver for Sicily only?

Thank you all for your replies!
I hadn't considered that the guides and drivers were classified differently and didn't do both.
And with suggestions of taking a suitcase that is larger than an airplane carryon (but not the largest one), I can see us fitting our clothes and still managing them on the trains.

The person who recommended his driver does splurge on his travel. While I can afford it for this one trip, I don't like to waste money if I don't have to. We are very mobile, but I've read so many posts about how lugging suitcases and walking cobblestone streets are very wearing. I guess I wanted to make sure it was a trip we would enjoy and not have it be a work out. I will look into a driver for Sicily. That makes sense.
Thank you everyone. This was so helpful!

Glad to hear! Yes rest assured you can pay for drives and such in an as needed basis and spend that extra on great meals and such.
On thing I often do is ask the hotel about transfer, sometimes just hopping in a taxi will do the trick though.