11 Nights Mid-September - seeking suggestions

Hi Jacey, during our last stay in Florence, we stayed at a hotel bordering the Ponte Vecchio - Pitti Palace al Ponte Vecchio. We enjoyed the location & the breakfast room looked out over the river w/ a lovely view of the dome, etc. I'm not sure how to avoid crowds in Florence. ; )

It looks awfully rushed--have you been to Florence or Rome before? I am firmly of the opinion that there are not "musts," and I have been to Italy six times without setting foot in Florence, Rome, or Venice, but only one full day for Florence and Rome will bring up the same comment over and over. If you have no interest in spending longer there, then no worries! I do however, think you may be discounting some of the travel times involved.
For the countryside, you typically need a car. There maybe some places you can get to and stay put, provided you did not want to do many day trips.
For "Tuscany" to the Amalfi coast, it depends on your ultimate destination, but typically train to Naples or Salerno, then bus, ferry, or private driver. If you are going to be doing a lot of day trips in all directions, then Sorrento makes sense--but it will not give you the wow factor you got from the photos of Positano. If Pompeii is your only must for example, then you can see it on the way to the coast.

2- On our three night stint in Tuscany, I would like to get the true Tuscan countryside, vineyard, wine class/cooking class experience. Which town is recommended for a good home base for this portion of the trip?
3- A friend suggested I rent a car for the Florence and Tuscany portion of the trip, but reading through the posts here I am wondering if that is a great idea. Is there an easier mode of transportation?

I'll answer 3 before 2. You don't need a car in Florence. Rent one as you head to the Tuscan countryside, where having a car can be a definite plus. You'll probably want to return it to Florence to catch the train to Sorrento.

We stayed at Castillo di Verrazzano, just outside of the charming little town of Greve. It's a wonderful winery. You can combine a tour of the winery with a wonderful food and wine pairing. There are a number of cooking classes offered in Greve. We loved La Cantina. The owner Alessandro was a gracious host. His mother, Mama Lorena, offers cooking classes.

There are a number of charming towns nearby and Greve is on the famed SR222. Greve is only 18km south of Florence so you won't have far to drive to return the car. There are a number of festivals in September, you can check them out.

Hello Jacey,
1- it is very crowded very close to Ponte vecchio, but I'm sure one street behind must be better. I would lean towards being a bit further. I was in Santa Croce.
2-The most "tuscan" of tuscany is around buonconvento, montepulciano, montalcino, pienza.
Road Sp146 from san quirico to pienza to montepulciano is a pure delight..
Then sp146 and sp40 and sr2 to go back. This is the most famous circle you can take.
3- so yes rent a car for that portion, you won't regret
4-I always have a car, couldn't talk about train or other transportation
5-Sorrento is more practical for transportation. But go to positano, Amalfi, ravello other by boat or bus. Absolutly worth it.
I'm still in Italy as I write this.
In Padova at the moment and leaving for dolomites tomorrow.
I was in tuscany for the second time just last week.
You can see my blog for some ideas. It's in french but you can google translate I'm sure.
I'm putting it at the beginning of the tuscan part, but you can change dates on your right.
http://famillecyrstgeorges.blogspot.it/2017/06/jour-2-orvieto-en-ombrie-et-une-arrivee.html

Part of the nice drive was this:
http://famillecyrstgeorges.blogspot.it/2017/06/jour-4-entre-montepulciano-et-pienza.html
I hope this helps.
Ciao
Claude

1. It depends on which hotel. I can think of some very near the Ponte Vecchio that are tucked away of side streets very few tourists use and others where you'd walk out the front door into a crowd.
2. I stayed in Montalcino and really enjoyed it. Easy driving to sights and vineyards in the surrounding countryside as well as to Pienza and Montepulciano, but not sure if there's a cooking class. If you stay in town, be sure to verify driving route to the hotel to avoid ZTLs.
3. & 4. Have you considered picking up a rental car as you leave Florence and dropping it off when you arrive in Sorrento? You'd have to weight the costs as well as your comfort level in driving on the autostada.
4. Returning to Rome is about an hour faster from Sorrento than from Positano. I tend to stay in Sorrento when I plan to day trip and in Positano when I just plan to relax.

Thank you all so very much for your advice and recommendations; they have certainly cleared up a few things for me!
In Florence, I would like to say at Hotel Lungarno, which appears very close to the Ponte Vecchio. We will wait to rent a car upon leaving Florence for the countryside. I would love to drive to Sorrento if it is not cost-prohibitive or unduly stressful. I just don't know what to expect having never been to Italy. I read a lot about International Drivers Licenses, ZTLs, and exorbitant fines and these things have given me pause on driving more than necessary!

I am thinking Sorrento will be right for us, with day trips, hopefully as many via boat as possible.

I will spend the afternoon checking out buonconvento, montepulciano, montalcino, pienza, and greve.

Jean and Doug Mac have given you excellent suggestions regarding lodging.
Doug's pick of Verrazzano is right on in terms of food (yum)
And wine.

From Greve, which is a cute town, none of the towns are a long distance away.
Panzano, Castellina, Montereggioni, Radda and Gaioli are under 1/2 hour. The towns of Montalcino, Pienza and Montepulciano are 1H20m

You can usually hit 2 a day.
Here's some info on wineries.
In chianti.
http://www.winewordswisdom.com/travel_itineraries/chianti-classico-wine-tour-part1.html

Look at his list for southern Tuscany also.

It's a debate as far as train vs car to Sorrento. The time and cost for both is about the same. If you're comfortable with driving, it does have the advantage of going when you want, and stopping when the urge hits you. Only you can decide.

I would agree that with those destinations and the distance between them your trip will be rushed. Plot out on on a piece of paper of spreadsheet how much time you would have at each of your destinations, and how much travel time.

For example, on your arrival day (what time?) you'll arrive, go through immigration, pick up your bags, take some sort of transportatio from the airport to the train station, take the train to Florence. Making sure to leave enough time so that if your plane arrives late, you can still get to the train station on time. Take train to Florence. Take transportation from train station to your hotel, check in. That will eat up 4-5 hours out of that day. Then you will have one full day in Florence, and as much of the next day as you want to spend there. Do that for each day of your trip, and decide if the ratio of travel time vs. enjoying time is the correct ratio for you.

Use Google maps to figure out the travel time from Tuscany to Sorrento. We did that drive, years ago, and while it was ok, only parts of it were scenic. And I will comment, I'm used to driving in big cities, and lived for a while in Boston (crazy drivers), but the drivers in Sorrento, I found, were pretty aggressive.

I would suggest dropping one of your destinations; I would suggest Florence as it seems to be the outlier, but if you really like Renaissance art, then don't drop Florence!