Ravello is perched high on a cliff with less transport than even Positano. If you don't plan to go to any towns on the coast and just stay put, it would be ok (unless you have a car?).

Two nights in Rome only gives you one sightseeing day.

For search purposes, Siena has one n.

I don't know that you would save any money with a rail pass since you would have to purchase seat reservations also (10€ - $14). Perhaps if you can use it on the train from the airport to Milan it might break even, but Trenitalia doesn't sell those tickets (at least not online) as those are sold by Trenord (12€). Not sure Trenord accepts the pass. If that leg isn't included, full fare walk-up price is a couple of bucks cheaper than a 4 day saver pass (currently $213 per person) + seat reservations (mandatory). If you are using a car for any portion such as Tuscany, you would likely pick it up in Florence and drop it in southern Tuscany (Chiusi? Orvieto?) and then your train cost would be even less.

You might also consider taking the Sena bus from Siena to Rome's Tiburtina station (20€). From there, catch the Italo train on to Naples. It takes the Sena bus the same amount of time to reach Rome and doesn't involve changes as the train does (either in Florence or Chiusi).

http://www.sena.it/Home/78-1-en.html

http://www.italotreno.it/en/Pages/default.aspx

If you're taking the bus from Siena to Rome Tiburtina, you could switch there to the Marozzi bus to Sorrento -- if it fits your schedule. From what I can read of the Marozzi schedule, this bus leaves at 3:00 PM. Probably you should get reservations: www.marozzi.it (all in Italian).

Santa Marharita Ligure (sp?) makes a sweet base from which to visit the Cinque Terre - I did that and spend a day hiking between all the villages but found SML a much more real town to stay the night.

SML attracts tourists who come to see nearby Portofino but is also a real active fishing town - watching the day's catch come is in the afternoon is a real sight.

Had to go away on a biz trip. Finally getting back to making all the arrangements again.

I need some help on few more things. Here is my final Itinerary -

Sept 7th - Fly out of JFK into Milan
Sept 8th - Getting into Milan at 8:30am.
Sept 8th - Take a train from Milan to Venice.
Sept 8th - 11th - Stay at the Westin Regina in Venice.
Sept 11th - Take train from Venice to Florence.
Sept 11th - 14th - Stay at the Villa Armena in Siena
Sept 14th - Take the train from Florence to Naples.
Sept 14th - 18th - Stay the Hotel Buca di Bacco in Positano
Sept 18th - Take train from Naples to Rome.
Sept 18th - 20th - Stay at the Westin in Rome
Sept 20th at 1:30pm - Fly out of Rome to JFK.

I mainly need help in getting around between cities.

1. Train from Milan. I plan on taking the train around 12pm. Will that be enough time (clear customs, get to the train station, etc.). Should I book 1st vs 2nd? Is there a big difference?

2. From Venice to Siena, is the best way to rent a car in Venice and drive to Siena OR take the train from Venice to Florence and rent a car in Florence to get to Siena? Are the train stations / car rental places nearby in Florence?

3. It looks the best option from Florence to Naples is on the Italo. Is that a fair statement? What is the best way to get to Positano from Naples?

This isn't working well as a layout. You can't be staying in Venice on the night of the 11th and departing to Siena the same day. You can't stay in Siena, travel to Naples and stay in Positano all on the 14th. I do not see how you can stay at the Westin in Rome on the 20th and also fly out on the 20th. I think you know your plan, but it is confusing and makes it look as if you have more time in places than you actually have.

Sept 8, arrive Milan, train to Venice, sleep in Venice
Sept 9 & 10, Venice (3 nts, 2 days)
Sept 11, train, bus/car from Venice to Siena via Florence, sleep in Siena
Sept 12 & 13, Siena (3 nts, 2 days)
Sept 14, travel from Siena to Positano via Naples, sleep in Positano
Sept 15, 16, 17, Positano (4 nts, 3 days)
Sept 18, travel from Positano to Rome via Naples, sleep in Rome
Sept 19, Rome (2 nts, 1 day)
Sept 20, depart Rome

My bad for the confusing post. Hopefully this is better?

Sept 8th - Travel from Milan to Venice via Train
Sept 8th - Check in to the Westin in Venice (3 nights)
Sept 11th - Check out of Venice and travel from Venice to Siena (Car/Train)
Sept 11th - Check in to Siena (3 nights)
Sept 14th - Check out of Siena and travel from Siena to Positano (Car/Train)
Sept 14th - Check in to Positano (4 nights)
Sept 18th - Check out of Positano and travel to Rome from Positano/Naples via train.
Sept 18th - Check in to Rome (2 nights)

Driving in central Florence is not advised because of the likelihood of stumbling into a ZTL, a locals-only driving zone. Which will likely result in a large fine some months later. You could pick up a car in Siena, but I prefer the idea of getting a rental car as you leave Venice. You'll probably want a car while you're staying in Siena anyway. You could stop along the way to Siena, maybe in Ravenna to see the mosaics.

Getting from Siena to the Amalfi coast, no need to go back to Florence. You could drop off the car and catch a train in Chiusi or Orvieto. Or even in Rome at the train station, but, again, driving in central Rome is not for the faint of heart.

In Naples Centrale train station, you can go downstairs and catch the commuter train, the Circumvesuviana, to Sorrento, then a bus to Positano. Or you can have a driver pick you up in Naples and drive you to Positano. Thirdly, you could take the train on to Salerno and take the bus or a boat back to Positano. Check the boat schedules carefully if you decide on that option.

Hiring a driver is much the easiest option but not cheap. Search the forum for recommended drivers and the cost of this option.

Do you intend to see anything of Florence? You could take a daytrip by bus or train from Siena into Florence, but that wouldn't leave much time for Siena and the beautiful area around.

>>>Sept 7th - Fly out of JFK into Milan
Sept 8th - Getting into Milan at 8:30am.<<<

You seem to be confused with arriving at the airport (not in Milan) with actually into Milan. Do you mean you will get into Malpensa at 8:30? It will take you about an hour to get from the airport into Milan (depends on whether you take the shuttle bus or the train). There is no class selection on the train - all one class - cattle. Are you planning to do something in Milan in the morning?

>>>Sept 11th - 14th - Stay at the Villa Armena in Siena<<<
>>>Sept 11th - Check in to Siena (3 nights)<<<

Villa Armena may be in the province of Siena, but it is not in or very near the town of Siena (it's closer to Buonconvento).

By staying so remote in Rome, you will not have the time to do the things you think you will. You are only giving yourself one sightseeing day and you are staying far out of central Rome. When you stay at remote places, you eat up a big chunk of your time trying to reach things. For such a short stay, I suggest you book something very central and walkable (Piazza Navona area or within a few blocks).

Good choice of hotel in Positano - excellent service and great location. If you are at all into cooking, they also offer a cooking class.

For getting to Positano, you can either (i) train to Naples and then prearrange for a driver to pick you up and drive you to Positano, or (ii) train to Salerno, then ferry from Salerno to Positano (but be sure the train arrives in Salerno in time to catch the last ferry, which currently is at 3:30). Arriving in Positano by sea is always fantastic - and a very short walk to BdB!

Bookmarking

Amit10 -
It looks like you have a nice amount of time to spend. One thing to consider, is that if you're not interested in Rome, you don't have to spend time there. Just stay there the last night to get to the airport. Have one lovely dinner, see the sites lit up at night and nothing else. Skip the museums and crowds. Go another time.

And in Tuscany if you've got a car, you can stay in one of the small hill towns such as Montepulciano and skip Florence and Siena. I would. That's much more relaxing and the countryside is such an important part of the best of Tuscany. Just wanted to throw that out there for you to consider.

Positano will be lovely!

Amit10, word on the street is that at the end of June Travelmar/Coop Sant Andrea will be adding an additional ferry from Salerno to Positano - departing Salerno at 5:10. So be sure to check the ferry schedule when booking train tickets.

Hey all, My husband and I are flying out of Charlotte to Rome on 10/5. We went thru a travel agent for parts of the 10 day trip. We have already booked our trains, we are landing in Rome at 9:45 am and are scheduled to catch the 11:12 from the airport to Rome, I'm getting nervous wondering if this is enough time. We are traveling light, just carry on luggage and already have our paid train vouchers. Any advice? Thanks. We are then traveling to Florence for 4 nights, Naples for 3 and then Rome for 4. Mary