Rome, Montepulciano, Florence, Sorrento

Sounds like a great plan - fly into Rome and out of Naples (I love doing that rather than backtracking to the original airport.)

Just keep in mind that "train from Florence to Sorrento" will involve some transfers - you might already know that. Something to consider is taking the last leg of the trip from Naples to Sorrento via ferry. After hours on the train, you may be ready for a change of scenery. (If you do take the train, make sure you get the Campania Express - the Circumvesuviana is a commuter train that will get you there, but it is not the most comfortable, especially when you're toting luggage.)

When I stayed in Sorrento, we took a day trip to Massa Lubrense and toured a family farm which culminated in a "farm to table" meal served al fresco, surrounded by lemon groves. It was one of the highlights of my trip. Where, on the other hand, I spent a miserable afternoon on Capri, broiling in the hot sun while surrounded by throngs of tourists milling about. Capri is a beautiful sight to see from the ferry, but I wasn't as crazy about it when I actually got there.

Hello BobNJ, and welcome to the forum,

Have you found or priced any Rome to Montepulciano car services? It's over 110 miles and the driver will presumably need to return empty so it will not be cheap. Montepulciano is not served by train but there is a "Montepulciano Stazione" which is still about 6 miles from Montepulciano proper. You can book a train there - with a change at Chiusi-Chianciano - and this is much closer and finding people who are doing the "last mile" connection should be much easier. And I would say the same for Montepulciano to Florence.

You have plenty of time to nail down the details, have a great trip,
=Tod

Wow….what a trip! LOVED Montepulciano….out in the quiet, a charming little town I could stay a month in, fun shops in town to explore. We also loved Florence but regret not writing down the lovely shops we passed on our first day walking tour as I wanted to go back and could not remember where they were! Wish you could go to Lucca……love that town! Sorrento was lemons everywhere…fun to shop them and enjoy their delicious food…..took a boat ride down to Amalfi one day where we bought an oil painting that reminds us daily of that trip. The boat ride was special. We were exhausted and opted out on a day trip to Capri so that we could relax at the hotel pool…..tho it was restful and had great views I regret that…..would love to have seen Capri!

Thanks for the quick and very useful feedback!

would love to have seen Capri!

If you saw it from the ferry, then you "saw" Capri! To me it was kind of like seeing the skyline of Manhattan from New Jersey. It is a jaw dropping sight that you don't see when you're IN Manhattan. (Not that Manhattan isn't a great place to visit, but just talking about the view of the skyline - it is best seen from across the river.)

I visited Capri for one afternoon, and it was basically thousands of tourists milling around the waterfront in the hot sun. I didn't take the funicular to the upper part of the island, so that might have been better, I don't know. But for me I was way more impressed seeing Capri from the ferry than actually BEING there.

Have you considered renting a car for your Montepuciano leg?
Driving us easy in that area
You could train to Chiusi and pick it up there, drop in Florence ( there are numerous threads here how to do that)

All drivers must have an IDP-required by law-get at your local AAA

We prefer hotels, especially for short stays and first timers
You have a 24 hour desk to help you, they will hold your bags before/after check in/out ( not usually an option with apartments) , offer bkft, etc
We only consider apartments for stays longer than 4-5 nights -too much hassle and I have no desire to spend time foraging for groceries and cooking while on vacation!
We don’t ever use airbnb

The classic first visit to Italy is Rome, Flornece, and Venice. Since NJ has better beaches than most of Italy (and Sorrento has only one tiny beach, sandwiched between two smelly marinas), I would not go to Sorrento on your first visit. We spent five nights in Sorrento on our sixth (?) visit to Italy. While it's easy to use four nights in Sorrento, I can't imagine less time in Rome! I consider Venice a magical place that is not to be missed. Sorrento is fine, but it's missable, and you'll get there eventually. You have not mentioned Pompeii. You need more time to get to the Naples airport from Sorrento than to get to the Rome airport from Rome. Traffic and road conditions are kind of third-world in Southern Italy.

Have you priced car services yet? This is going to be prohibitively expensive, so you need to reconcile yourself to train travel. It is very desirable to have a rental car to make the most of Tuscany. It may be less crowded in October, but I hope the local tours you will need are still operating in October. (No personal experience, we rented a car in the summer. And I don't "like" renting a car.)

Great advice on using the trains as much as possible. There will be plenty of taxis for that last mile and you will save hundreds. The only place I would use a car service is along the Amalfi coast, although the ferries are a beautiful way to see the coast.

While I agree you will “see” Capri” from the coast, you need to experience it. I loved Anacapri for an afternoon of glitzy window shopping and people watching but, if you are fit, we really enjoyed walking down the other side to some beach clubs on the rocks. Stunning and fun.