Italy Itinerary Help!
 

This is the itinerary that my husband and I planned for our trip to Italy at the end of May. It's his first time to Italy and I studied abroad in Rome 9 years ago and got to travel around quite a bit and am in love with Italia:

- land in Rome in the evening, hopefully sleep off the jet lag

- 4 nights in Rome

- day in Pompei

- 3 nights in Arienzo (right outside of Positano)

- 3 nights in Florence with daytrips to Val D'Orcia and Chianti

- 1 night in Venice (just to show it to him, but I don't particularly love it and think 1 night suffices)

- 2 nights in Lake Como

- 1 night in Milan

- Fly out of Milan

It is of course very difficult to cut anything out of the itinerary, but I also don't want us to be so rushed or to spend so much time on trains/buses that we miss the biggest joy of Italy (which is the beautiful lifestyle of relaxation).

Some specific questions:
- Would it be better to spend the last 3 nights in Milan with a day trip to Lake Como and then 1 day wondering around Milan before we fly out the next day or does Lake Como really deserve an overnight stay? Neither of us has been to Lake Como, so not sure what to expect (other than beauty).
- Since we are only staying in Venice for 1 night (IF we don't cut Venice out of the itinerary altogether), would it be a bit help to stay close to the train station? We found a hotel very close to the station, but it got mediocre reviews. We found a better option that's right by the San Salvatore water bus stop.

The biggest travel time in this itinerary is going from Positano to Tuscany. Since we want to see the Val D'Orcia and Chianti, is there a better Tuscan base other than Florence that we should go to?

Any and all suggestions are greatly welcomed!

>>>3 nights in Arienzo (right outside of Positano)<<<

I assume you mean near Arienzo beach, not the town of Areinzo which isn't close to Positano?

Are you planning to rent a car? You can't easily see Val D'Orcia and Chianti without one.

Do you mean the San Silvestro water bus stop? Personally, I would not choose a hotel close to the train station unless I had a very early train departure time or was planning many day trips by train. I would want to stay in Venice closer to the sights I was interested in seeing, especially with so little time. I would probably give Venice another night so you would have a complete day there, but I don't like one-night stays. You also might find that you like Venice better when visiting there with your husband.

Without knowing your interests, it would be difficult to judge whether three days on a beautiful lake would be a better choice than three days in a modern city. Why did you choose Milan and Lake Como? What do you plan to do in each place? You might do 2 nights in Lake Como and two nights in Milan, which would give you at least one full day in each place to explore.

Yes, I meant Arienzo beach and yes, we are renting a car in Tuscany. We are going to spend 3 nights in Florence as of now and rent a car on our 2nd day there and drive to Val D'Orcia/Montepulciano and then maybe Chianti the next day and spend the evenings when we're back from day tripping checking out Florence itself. Thoughts?

ellenem, yes - I meant San Silvestro water bus stop, but we actually switched hotels to be only a 5 min walk from San Lucia Train Station so that we don't have to lug luggage through Venetian streets 2 days in a row.
We are only going to Milan because that's where our departing flight leaves from. We were interested in Lake Como simply because it looks gorgeous and it will be nice to get some relaxation time. In Milan, the only plan we have is to check out the Piazza del Duomo and in Como, we hope to just explore, relax, ride some ferries, and take in some amazing views. Do you think it makes sense to spend the night in Lake Como instead of day tripping from Milan? The only positive I can see to day tripping is that it's a shorter train ride from Venice to Milan instead of Venice to Lake Como and also because it would might be nice to not have to pack and unpack our luggage every day. All advice is welcome! Grazie.

Re: Florence--"rent a car on our 2nd day there and drive to Val D'Orcia/Montepulciano and then maybe Chianti the next day"

You appear to still want to base in Florence for your day trips. Where will you store/park your car overnight? You are contemplating driving out of and returning to Florence which is problematic with the ZTL and parking issues. Once again, basing in Florence for driving visits to the Val D'Orcia and Chianti has issues if you intend to sleep in Florence. Consider a base outside of Florence and day trip by train or bus into Florence. Your call.

>>>We are going to spend 3 nights in Florence as of now and rent a car on our 2nd day there and drive to Val D'Orcia/Montepulciano and then maybe Chianti the next day and spend the evenings when we're back from day tripping checking out Florence itself. Thoughts?<<<

Bad idea. It's difficult to drive in the Florence area without crossing the ZTL and getting tickets (cameras everywhere and the ticket is mailed to you plus extra fee from the rental company for providing your info to the police). You aren't allowed to drive in the center of Florence (or center of many towns small and large) and you would have to park outside the center and transport in. Parking a car overnight will run about 35€.

I would pick up the car on the way from Positano to Tuscany in either Orvieto or Chiusi. Maybe stop in Montepulciano on the way through Val D'Orcia that day and spend the night in the Pienza area or Siena area. You could day trip around the area to other towns in Val D'Orica or Chianti. Drop the car in either Siena (easy bus or train ride to Florence) or Florence (airport location is easiest to avoid ZTL).

Get a map and look at the roads (scenic roads, not autostrada) from Chiusi through Val D'Orcia. I like this map for driving Tuscany.
http://www.amazon.com/Toscana-Tourin.../dp/8836528309

With a car, I don't mind a one nighter or two in small towns such as Pienza (very easy to drive in and out) or Montalcino and head on to another small town the next night (Castellina in Chianti?). If you want to stay one area, you could consider something sort of central to the things you want to see. This place is not too far from Siena.
http://www.mulinodiquercegrossa.it/

A one or two day car rental often costs as much as a three day rental. You might even consider picking up the car in Sorrento and keeping it until Venice or Como.

Another option if you want to stay in Florence the three nights would be hire Luca from Hills and Roads to tour you around a day. Lots of recs here and on Trip Advisor.
http://www.hillsandroads.com/

How does the day in Pompeii factor in? Are you stopping on the way from Rome? Spending the night?

Thank you all for the feedback, but what is ZTL? Our hotel in Florence is outside of the city center and allows overnight parking for 12 Euros/night.

We had thought about the option of taking the train from Positano to Chiusi and then staying around there, but that train ride is just as long as going all the way to Florence and if we base ourselves in Siena and get off in Chiusi, that means we just have a one hour (minimum) drive ahead of us after having just taken a 4 hour train ride, so it didn't seem like the best option.

Is it really so bad to have the car in Florence and use that as our base to explore Val D'Orcia?

Re: the question of Pompei, we are stopping there on the way to Positano from Rome.

Never mind re: my question about the ZTL. I just looked it up and our hotel seems to be out of the ZTL range (the hotel is on the other side of the Arno), but I wonder if we'd have to drive through the center to drop off/pick up our car and potentially to venture out on the day trips.

Hi Eli,

I recognize your itinerary from Slow Travel! (swithers there)

Your car rental office will show you how to drive out of town away from the ZTLs, but it will be up to you to figure out how to get back to your hotel at night, and get the car to the rental office without getting a ticket. Your hotel should be able to show a way to do that.

But even you can negotiate that, you have a very long drive from Florence, a good chunk of it on autostrade, to get to the val d'Orcia from Florence. And you will probably want to leave the area by 4pm or so in order to get back for dinner in Florence, and that makes for a fairly short day.

Taking the train in Italy is pretty relaxing, so I don't think you'll be too tired to drive if you pick up a car in Chiusi and drive an hour to Siena. Plus the drive is very pretty, especially in the late afternoon light if you go by way of Montalcino. It will make the drive longer, but you probably won't care.

Yeah, I know that the drive from Florence to Val D'Orcia will include a lot of autostrada driving, but wouldn't Florence be a better base if we want to visit both Chianti and Val D'Orcia? I'll start looking for accommodations in Siena in case we do decide to go that route. Thank you for the suggestion!

For those who have been following this thread, I wanted to let you know that we've decided to stay in Firenze and day trip to Chianti and maybe Lucca. We'll save the Val D'Orcia for another trip and I'm hoping we'll see a lot of rustic/country/small town beauty in Chianti too. If anybody has any suggestions for specific spots in Chianti, please let me know. I think that should be a fairly manageable day trip from Florence.