Proposed two week Itineary - suggestions for travel and transfers

You appear to have allowed for travel time between your destinations. You get an A for that, not everyone does:)Answering specific questions you had (your itinerary in italics):Day 4-5 Fly (or take train?) to Florence Take the train, flying is not worth considering for that legclick here to see train schedulesDay 6 - Rent Car in Flornece to tour Sienna and San G.If you pick up the car in Florence, give a very wide berth to the Florence historic city center, someone here just got 10 tickets @ $125 = $1250 for driving into the Florence city center restricted traffic zones; in fact, consider picking the car up at the Florence airport (but don't fly from Venice to Florence), at least don't pick it up at the Florence train station.It's rare for people (on this Board) to fly from Rome to Venice, most take the train. That's a 4.5 hr train trip, a rule of thumb followed by some veteran travelers is: Don't consider flying unless the trip by train is more than 6 hours (trains go city center to city center, airplanes don't).

"Would you skip orvieto and spend two nights in montalcino instead of one and then drive straight from there to rome on Day 7?"You're going to arrive at Montalcino at 7 or 8pm and only have time for dinner before falling into bed. If you only stay one night, you'll have to get breakfast, pack up, and check out by checkout time, which in a smaller Italian hotel could be 11am. That leaves little time to explore Orvieto.For that reason, my personal preference is to minimize one-night stays as much as possible, so if it were me, I'd do 2 nights in Montalcino. And then turn the car in at Orvieto and take the train (75 mins) from Orvieto to Rome. I have never driven in Rome and don't intend to start now.I don't know the best advice for the Rome to Salerno leg.

Thanks for the suggestions.

Day 6 - Can one see San G. and Siena late morning and early afternoon with sufficient time to get down to Montalcino?

Would you skip orvieto and spend two nights in montalcino instead of one and then drive straight from there to rome on Day 7?

Day 7 - do you think it would be easier to drive from orvieto to Rome to drop car off in rome (as opposed to Orvieto) and then transfer to train to salerno to take boat to amalfi coast?

Day 6 - Can one see San G. and Siena late morning and early afternoon with sufficient time to get down to Montalcino? Well, let's think it through a bit.You wake up, pack up, check out. Then you have to get transportation to the car rental pickup place, do the rental paperwork, get in the car and drive out of the parking lot. When you actually get on the road depends on several variables, including what time the car rental place opens in the AM, maybe not as early as here (I don't know but you can check online).Let's assume you're driving out of the car rental place at approx 1000, that puts you at SG at 1115 (if you get out of Florence without getting lost, GPS will help). At SG you have to park, walk up the hill. So you're walking through the gate at SG about 1145. You want to have time to walk around, climb a tower, etc, a minimum of 2 hours to do that and have lunch. Then back to the car, so you're not headed to Siena until at least 1400 (2 pm).Arrive Siena at 3pm, finding parking and walking to Piazza/Duomo gets you started sightseeing in Siena around 3:30.There's a lot in Siena, the minimum walking around there is a couple of hours. By now it's 5:30, 30 mins to walk back to your car and get on the way to Montalcino.So on the way to Montalcino about 6pm. If you have a GPS, you probably get to Montalcino by 7 to 7:15, if you don't, who knows? Find parking, find the hotel, check in, unpack, it's probably after 8pm, in time for the traditional late Italian dinner.That gives you only 4 hours of sight-seeing in the entire day. If that's enough for you, it could work--depends on what time the car rental opens in the morning and whether you get lost on the three driving segments (likely without a GPS).My personal preference: I'd want more than 4 hours of kind of rushed sight-seeing in a 14 hour day. But that's just my preference.

that was very helpful indeed. I suppose by your suggestion of staying two nights in Montalicno I would skip Orvieto or simply see on the way to drop off the car. Maybe that would be a waste of time and there is a way I could drop off car in Montalcino and taking a train from there?

I know, trip planning can be frustrating, because there's only so many days and so much to see! Something usually has to give. I'm not trying to tell you how to travel or trying to substitute my own travel preferences for yours. Just trying to help you think through the consequences of certain choices: if I choose to see this and do this, then that means I have less time for this, or take a day away from this destination, etc. You could choose to do a one night stay in Montalcino instead of two nights. The consequence of that is, when arriving in Montalcino at 8pm the night before, and then having to check out the next morning, constricts the amount of time you have in Montalcino--but perhaps you would prefer that, so you can have more time in Orvieto?Unfortunately, there are only so many days and there's so much to see. Every time you change hotels, it eats up about half a day (not including your travel time to the next destination) just in the logistics of packing up, checking out, finding the next hotel, checking in, unpacking--and then the same thing day after day, it consumes a large part of your trip that you no longer have for doing the things you're going to Europe to do. Other choices: You could choose to take the bus from Florence to S.G. and then to Siena; and pick up the rental car at the Siena train station (in the flatland away from the Siena historic center). Or take the bus from Siena to Montalcino, and pick up the car in Montalcino. But once you have the car, you'd want a day or two to explore Tuscany hill towns, instead of just leaving the car parked in Montalcino or Orvieto all day and not using it.

I appreciate that input. I am trying to maximize my tour and enjoyment time and minimize travel while in Italy.

The challenge of this iternary is finding the fastest way to get from Tuscany (Chusi/ Montalicino or alternately Orvieto) to Positano as we have put Rome at the end of our trip to fly out of. I haven't figured out the solution for that because of all the logistics in getting to Positano from the Tuscany area.

I bit my tongue (or rather my keyboard?) for a while to see what others might say because I am so opinionated about this.. Here goes: Day six doesn't seem realistic to me, even for those who move faster than I do. I recommend that you select destinations that are either well served by public transit and ditch the car, or get a car and visit towns that are convenient to reach by car, but don't mix and match.

A car is useless in Siena and San Gmi. But, worse than that, it will cut into your sightseeing schedule.

For example, if you take the bus into Siena you will conveniently disembark in the middle of town. If you rent a car, well not only do you have to spend time getting to your car rental, I find it's a bit confusing driving near Siena (could just be us, but others say that too). Then you have to find parking. I've talked to some people who spent an hour looking for parking, this board has stories of people who looked for two hours. Who knows what you will experience, you may find parking in 30 minutes, but can you afford to take the chance with your tight schedule? Of course, once you find parking you still need to get back and forth from your parking lot to town. The only destination that might favor a car is Montalcino, but you won't really have time to see it.

So, here is something to think about using your wish list. Plan A--Public Transit itinerary: Visit San Gmi and/or Siena and stay in Siena without the burden of a car or Plan B--Off the beaten path options: If you rent a car, then enjoy places not served by transit. Enjoy the small towns between Florence and Montalcino and Tuscan hilltowns. Visit some wineries, Etruscan tombs, the neat abbey near Montalcino (is it called San Antimo??)and forget the big cities. The small towns will have plenty of free, safe, proximate parking-- not mention fewer dreaded ZTLs-- perfect for driving.

They're both wonderful itineraries with different things to offer.

Linda - I agree. I think that public transportation from Florence to San G. and then onto Siena is a wise choice....although I am not sure what to do with our luggage. Once in Siena we would rent a car to leave Siena and drive to Montalicino and stay there 2 nights to see the wine region etc and then off to Orvieto where we drop the car off, skip staying there and then onto Positano. Is there any way to store our bags somewhere in San G or Siena while we walk around those areas ?

And do you have any ideas of the best way to travel to Positano from Orvieto?

Terre: As of 2007 (unless it's changed since then), you can drop your bag at the S.G. TI in the old center on Piazza del Duomo, maybe you can verify that here: www.sangimignano.com