1 night + 2 nights = 3 nights = 2 full days, and you want to visit four places + drive a total of 7 hours minimum + avoid getting tickets for violating limited traffic zones + find parking everywhere. This does not compute.

This winery claims it is the only Kosher winery in Italy.

http://www.terradiseta.it/eng/aboutus.html

Jean, thanks! Here's our full itinerary... probably need to modify and certainly open for suggestions:
3 nights Naples
4 nights Rome
1 night Sienna
2 nights Florence
1 night La Spezia
1 night Milan
3 nights Venice
We are traveling in February.
Our thought was leaving Rome early and getting to Pitigliano before noon. Touring the city, leaving there and doing a winery on way to Sienna. Spending evening and next morning in Sienna then driving to Florence stopping in San Gimignano. I'm beginning to think we need to cut out Milan and add a day to Tuscany - either in Sienna or Florence. What do you think?

>>>We're planning to stay 1 night in Sienna and 2 nights in Tuscany <<<

Siena is in Tuscany. What do you mean by 2 nights in Tuscany?

What day of the week do you plan to pick up the car?

Kybourbon -- I meant to type Florence but it came out Tuscany! We'd pick up the car Tuesday, Feb. 19.

I think I'd eliminate La Spezia and Milan and add those nights to Siena and Florence or Venice. They seem out of the way for 1 nighters.

Have a great trip whatever you decide!

I don't do multiple one-nighters and definitely not three in one trip. I wouldn't go out of my way to visit La Spezia in February, and though I like Milan more than most here I don't think it makes sense in the itinerary for this trip.

Rome to Pitigliano to Siena is more than 4 hours of driving. Add a few hours to explore Pitigliano and finding/touring a winery, and you could be driving to Siena in the dark. Siena has a limited traffic zone, so you need to be very aware of how to legally reach your hotel there. Are you comfortable doing that in the dark?

I'm curious about the one night in La Spezia. Is there something in particular you plan to do/see? I would drop La Spezia and Milan unless you had some absolute must sees in those cities.

Pitigliano is out of the way. If you weren't going there, you could take the Sena bus from Rome to Siena (about 10 departures daily - travel time 3 hours). One night in Siena does not allow for a day of sightseeing in Siena.

A one day car rental can often cost as much as a three day rental.

Have you already booked flights?

FYI - Siena has one N so if you are searching this website for info, you'll probably get more results with the correct spelling.

Thank you Jean and Kybourbon. We've decided to eliminate Milan and add an extra night in Siena or Florence -- another decision, but I'm leaning to Siena. The night in La Spezia was to hike Cinque Terre - my daughter said it's not bo be missed. We plan to go directly from Rome to Pitigliano - either renting a car in Rome or take train to Orvieto, rent a car, and drive to Pitigliano. Which do you recommend? Good advice on car rental... we'll keep it till Florence.

With an extra night in Siena we could do the winery the next day, spend more time in Pitigliano and and then drive to Siena before dark. We're taking a Jewish heritage tour in Siena in the morning. What else do you suggest in the area before heading to Florence?
Yes, flights are booked to Rome and out of Venice. You've been so helpful already!

If you pick up your car in Orvieto (worth a visit/stay), you must arrive there before they close for the afternoon (usually about 1-4). Also closed Saturday afternoons and all day Sunday. Pitligliano is about an hour drive.

>>>The night in La Spezia was to hike Cinque Terre - my daughter said it's not bo be missed.<<<
>>>We are traveling in February.<<<

That won't really allow hiking time (it will be dark early) and the weather in February can be iffy. I would drop CT as you don't really have time.

You need to plot out your trip and see if you actually have time for the things on your list. If you are flying into Rome, then I would stay there first.

Day 1 - depart for Italy
Day 2 - arrive Rome (recover from jetlag - don't plan much)
Day 3 - tour Colosseum/Forum + something else
Day 4 - Vatican Museums and St. Peter's
Day 5 - ?
Day 6 - Train to Naples (Naples or Amalfi?)
Day 7 - Pompeii ?
Day 8 - Naples?
Day 9 - Pick up car and head to Pitigliano (about 4 hour drive)
Etc.

http://www.ricksteves.com/news/cinque-terre/cinque-terre-disaster.htm check this out. I don't think hiking in CT is an option anyhow.
http://travel.nytimes.com/2012/11/25/travel/a-little-jerusalem-in-the-heart-of-italy.html?pagewanted=all&_r=0 we had a wonderful visit to Pitigliano!
http://www.jewishroma.com had a wonderful private tour with this woman.

Virginiafish - Thanks for the Rick Steves link! I'd heard about the disaster, but I'd also heard things were repaired... So you clinched the decision, we will have to skip CT. We'll add an extra night in Siena and one in Florence. We, too, have booked tours with Michaela in Rome and read the NYT article about Pitigliano one day after we'd booked our tour there

Kybourbon: we've completed most of the rest of the itinerary in just the fashion you listed above, assuring time for all the sites. It was this central part of the trip in Tuscany we were unsure about - and all of you have helped so much.

Here's what we have so far:

Fly to Rome and take train from airport directly to Naples arriving by noon.
Naples 3 nights – Feb 13-15 - Pompeii, Huculaneum, Vesuvius, Almalfi Coast

Rome 4 nights – Feb 16-19 leave early morning 20th train to Orvieto see underground, rent car and drive to Pitigliano tour of city and surrounding; drive to Siena

Siena 2 nights - Feb 20-21 tour city and Chianti region, San Gimignano. Other recommendations? Should we drop the car in Siena and take the bus to Florence? Drive to Florence and drop car there?

Florence 3 nights - Feb 22-24 - Should we include a visit to Pisa? if so... at what point do you recommend?

Venice Feb 25 through 27

Fly home Feb 28

So appreciate your help. It's made a big difference in our plans

I think you will want all of the time in Florence. We dropped our car in Siena and took the train to Florence. Driving around Florence looked challenging.

>>>Fly to Rome and take train from airport directly to Naples arriving by noon.<<<

I would be surprised you would make it to Naples by noon. What time does your flight arrive?

>>>Naples 3 nights – Feb 13-15 - Pompeii, Huculaneum, Vesuvius, Almalfi Coast<<<

Are you visiting anything in Naples?

>>>leave early morning 20th train to Orvieto see underground,<<<

You will need to store your luggage. Orvieto station doesn't have storage so you would have to pick up your car first and store in your car.

>>>Feb 20-21 tour city and Chianti region, San Gimignano<<<

Siena needs a full day. I don't think you have time for Chianti and San G.

I still don't think you've quite mapped things out timewise.
If you depart Rome on the 20th, train to Orvieto, visit pick up car, drive to Pitigliano, visit, drive to Siena it will be late by the time you arrive. You only have the day of the 21st actually in Siena as you depart Siena the 22nd.

I recently visited Florence and took a day bus trip to Siena and S. Gimignano. I'm so glad I chose to do it that way! No driving, parking, and transport was door to door.
The train from Rome to Florence is less than 2 hours and you'll be able to enjoy the trip and view rather than worrying about traffic, parking, etc.
Make Tuscany and Siena day trips from Florence. A lot less complicated. And seriously, how many times do you want to pack/unpack, lug bags up/down stairs, in and out of cars, ugh!

If you're going to that kosher winery, I hope you noted that you have to have a confirmed reservation and must choose either an 11 am or 5 pm time to visit - you can't just drop in. And the vineyards will be gnarly and bleak in February, though the visit might be interesting.

You really won't have enough time on that day for Rome-Orvieto-Pitigliano-Siena! Believe me, it will not work out. Partly because it just takes longer than you think to do this, and also because, having experience driving in that area, you do NOT want to be finding your way around the roads there in the dark. Unless you have GPS. It is not well lit at night, signs are not illuminated, only reflective, as I recall.

If you really want to visit Pitigliano, I suggest going to FCO and renting a car, then driving up the coast and cutting inland after you get approximately west of Pitigliano. I do not have a map at hand, but you can see the main roads if you look. However, I would then omit Orvieto, unless you want to spend the night there. in any event, you can't do all three places in one short-daylight day. You may also have bad weather in February, which will slow you down more.

Brosis,

I just saw your thread for the first time and if you are traveling in February, you need to be flexible with your driving plans. The law also requires you to carry snow chains or have snow tires in most parts of Tuscany, so make sure you get them when you rent your car.

I agree with the above suggestion to pick up your car at FCO (Fiumicino Airport). Even in bad weather, the coastal road is the least likely one to experience ice and snow.

Thanks to ALL of you, we have totally redone our itinerary for our trip. Here's what we now propose for the Umbria/Tuscany leg of our 16 day travels in Italy. Please let me know what you think:

We would leave Rome in the evening on Feb 19 and take a train to Orvieto to spend the night. We'd pick up a rental car in Orvieto on the morning of Feb 20 and drive to Pitigliano for our tour of the area, returning to Orvieto in late afternoon in time to visit underground caves and some of the sights.
Overnight Wed., 20 in Orvieto and leave in morning of 21st to go to Siena. We'd have the entire day to explore that city spending the night in Siena. We plan to leave early on Feb 22 to drive through the area, stopping to see towns of Tuscany San Gimignano and Monteriggioni and visit a winery on way to Florence. We would arrive in Florence in the evening, drop off the car at the airport, take a cab to the hotel and spend 3 nights in Florence.

Does that sound more reasonable?

Other thoughts/questions...
- snow in Tuscany? I guess, if the weather predicts snow, we'd follow the suggestions above and rent the car in Rome, driving the coast to Pitigliano and dropping the car in Orvieto and take trains/tours for the rest.
- Question? Do you think an automatic may be available in Orvieto?

I'm going to post our whole proposed itinerary on this forum once I get some response to this revision. I love Fodors. i've always gotten the best travel advice. Thanks to all of you!