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Hi dtph. After Venice, if you decide to take a Eurostar train south, then it will stop in Bologna and Florence. If you wanted to go by train straight to the Tuscan countryside from Venice, then you would still most likely stop in Florence and change to a regional train to take you to whichever Tuscan town you decide to base yourself in. I've not personally rented a car in any of the smaller towns in Italy, so I can't really give you advice about this, but because this whole area is a tourist Mecca, I'm sure it would be relatively straightforward.

If you decide to stay in Florence prior to touring Tuscany, then yes, I would recommend you pick up the rental car only when you are ready to leave the city. Parking can be tricky (and expensive) and traffic challenging in the cities, so I personally would avoid having a car with me until I really needed it. Likewise, if you tour Tuscany first and return to Florence at the end of your journey, I would return the car as soon as you arrive in Florence. Public transport options are good in Florence so you won't need a car while you're there.

I think 3 days in Venice is a really nice way to end your visit,
very relaxing, waves lapping and footsteps shuffling. You know how you always need a vacation after your return from vacation?
Venice is quiet, not like cosmopolitan Florence.
Don't get me wrong I love Florence too. It would be wonderful to have recent memories of beautiful Venice on your trip home.

Does anyone else have any thoughts on the order of the itinerary(keeping in mind that I will spend nights in each area)? I did do some reading on Tuscany as suggested and am interested in Siena, San Gimignano, Chianti, Montepulciano, Montalcino and possibly Pisa.

1.
Venice
Florence
Tuscany

2.
Venice
Tuscany
Florence

3.
Florence
Tuscany
Venice

4.
Tuscany
Florence
Venice

Your flight connections and prices will dictate. Avoid early departures from Venice---a real hassle.

Siena can be seen as a daytrip from Florence, as can Pisa. I'm not sure you have time to really enjoy both the Chianti and the area that includes Montepulciano/Montalcino. You can drive through both, but not really sink into both.

You might consider this:

See Venice
Take train to Florence.
See Siena as a day trip from Florence.
Rent car in Florence and head to Montalcino via Chianti scenic road.
Spend a few days in Montalcino poking around the countryside
Day before departure, drive to San Gimignano, then to Pisa. See monuments, drive to airport hotel either in Pisa or Florence, return car.
Depart next day.

Others may have other ideas.

Hi dtph. I think zeppole's itinerary is a good one.

Of course you do -- always good to agree with oneself.

We did three nights in Venice, three in Florence, and five in Tuscany (based in Pienza). It was perfect for us.

Good catch Surfergirl.

If you are going to visit Siena and want to visit Montalcino/Montepulciano, it makes more sense to pick up the car in Siena, not backtrack to Florence or pick up the car in Florence (Florence is notorious for traffic tickets for people unknowingly entering the ZTL) and visit Siena on your way to Montalcino (only an hour south of Siena). Siena has much more parking access so it's not so difficult to make a stop. It really depends on your flights in and out as to which route will make the most sense.

Wooders101 is not me. Different poster.

By the way, you two -- surfergirl and kybourbon? You both really should just get over me. You're not doing yourselves any good.

If you look above, you'll see that Wooders101 recommended le Cinque Terre, which I rarely do because it is so touristy, and also talked about doing "justice" to it with a fixed-3-day mindset -- an approach to travel I've opposed so vociferously on Fodor's the snarling tourist pack has repeatedly ripped me to shreds.

Wooders101 thinks more like you all than me.

Also, I have rented a car in Tuscany, and didn't know about the Chiantigiana road until Wooders101 brought it up.

"Good catch"? No, hate speech.

Listen, before you two and others go stalking poor Wooders101 all about the boards to bite his or her ankles with sour accusations of being me, click on the screen name and note all the advice about Australia. I've never been to Australia and know nothing about it.

Sorry dtph! Just wanted to nip that ninny-behavior in the bud!

(Childish behavior, I should have said.)

Wow---another record for Zeppole !
Six consecutive posts in less than :20--never ceases to amaze.

Wow, who would have thought I'd cause such a mystery. Nope, zeppole and I are definitely not the same person....

regardless of who you all are - thanks for all your help!