Itineary help needed starting and ending in Milan

We stayed in Sorrento over New Year's 2012>2013 (yes, definitely a different time of year than in your plans). Our B&B host, a local chef, said if he was to pick one time of year that would be the best for visiting Sorrento, it would be April, for the best combination of good weather and minimal crowds. We took the ferry for a day trip to Capri, and the seas were too rough that day to permit entrance to the Blue Grotto, and that was our one chance that trip. If you had more than one day on Capri, that would give you more options to account for weather and waves. We had a car, which was handy for getting to Pompeii, Herculaneum, and other archaeological sites from Sorrento. We also drove the spectacular Amalfi Coast drive ourselves, so didn't hire a driver or use a bus, but, again, December/January have fewer tourists than some other times of the year. We didn't take a trip to Vesuvius.

In reference to the blue grotto, if you can't get in there (it is supposed to be best in the morning, not afternoon when we wanted to see it) then you can also have a private boat take you around and you can see other beautiful grottos....

and since your plans include many things along the circumvesuviana, I would probably select Sorrento......

Thank you Cyn and Katherine

If we use 1 or 2 towns as home base is it possible to rent a car for the day? Driver for the day? Local public transportation?
Yes, certainly possible almost everywhere in Italy. Firenze is worthy of at least 3 nights, more if you use it as a base to go elsewhere. The only caveat I would add on car rental is that many locations do not have Sunday hours so plan accordingly. As Firenze is quite far north in Tuscany, concentrate on Chianti and Siena areas using it as a base. Move to Assisi or Perugia areas to see Umbria more efficiently. We "did" Umbria without a car a few years ago, basing ourselves in tiny little Spello.

Personally I would not have a car on the Amalfi Coast. It can be well-experienced using public transportation. Use Sorrento as your home base.

If you have time, Paestum might be an interesting addition.

Thank you Laurel and Zoe for your suggestions

As Zoe mentioned, Paestum is great! A little harder to access from Sorrento, I would say its a bit easier on the Amalfi Coast side, but great nonetheless!

Please read enough old posts to decide whether you prefer the Amalfi Coast or Sorrento. Transportation is much easier from Sorrento, but even bustling Positano has a more beach resort feel. A car is a liability in either place.

Thank you Tim

Joanne, I did the JFK - Milan - Vernazza trip May 2014. I am 61, I was pretty tired, but re-energized quickly. I don't get hammered by jet lag, fortunately. It is doable. I did not buy train tickets in advance as flight arrival, etc., is not always dependable. However, if i did that again, I would definitely purchase my return train ticket to Milan in advance as I would have control over the time I left my last destination.

Hotel Garda in Milan is inexpensive, quite nice, and a 5 minute walk to Milano Centrale Station for the return to MXP when the trip is over. Hotel Berna is another hotel that is right across the street.

2nd question:

We always fly open jaw but after checking prices I'd like to know your thoughts on flying found trip from NYC to Milan to save approximately $1,000.00 for 2 tickets.

Checking airfare today, prices round trip from NYC - Milan are under $700.00. Open jaw from NYC to Pisa or Florence and returning from Rome or Naples are $1,100 to $1,300.00.

Our travel dates are flexible. We plan on leaving around 4/16/15 and returning 5/2-5/5. This will be our 2nd trip to Italy(1st trip Venice, Florence and Rome)

This trip we want to see; Cinque Terre; Tuscany and Umbria, Sorrento, Capri,and the Amalfi Coast along with Pompeii.

We could fly to Milan and go directly to CT and then continue south. Add Lake Como for end of trip and return to Milan for flight home.

We could also leave Sorrento and stop for a night or two any way to Lake Como.

Would like you advice and thought on this itineary. We have 16-20 travel days to play with not including 2 days for travel.

Open jaws is a great concept, and can be efficient, but isn't necessarily always the way to go - especially if your beginning and ending locations aren't thousands of miles apart, or if you can save $1,000 !!! If Milan makes economic sense, and it doesn't require too much time or money out of your vacation, it sounds like a good deal.

Thanks Cyn. $1,000 is a lot.

In and out of Milan MXP or LIN sounds good. Milan seems to be more economical than ROME FCO. A car for touring Tuscany region sounds fun but may be a hassle in Amalfi coast where could be an issue. I have not tried driving in Italy. I find trains and buses even boats are efficient and convenient. I took an enjoyable bus tour of Tuscan wineries from Florence. In the south Sorrento is a great base to explore Naples and Pompeii, Herculaneum and Amalfi coast. Boats and buses available. In order to be in Amalfi coast itself I stayed two nights at small town of Amalfi which is closer to Paestum via Salerno. Positano was nice but pricey. Your travel plan is ideal because you can see the differences between north and south with enough time. I have been visiting Italy by regions within 7 to 10 days only.