We have about 1 1/2 days in Tuscany starting on 5/1 we can leave Florence around 2 pm and head out. We need to be back in Florence on 5/3 by 10am.

I'm looking to visit some of the following cities and would like some help narrowing down what is reasonable to do in this amount of time and which cities are the highlights. We are less intersted in art and museums and more interested in scenery. Here are some of the cities I was thinking of:
San Gimignano
Siena
Monteriggioni
Montepulciano
Cortona

I know that this is too much to fit into that time. Please help me narrow down what you would recommend.

Hi jl,

You could stay in Florence and visit Siena and/or San G as daytrip(s).

You could move to Siena for a night and visit San G, or another town, from there.

Many folks have posted that they were charmed by Siena at night.

I'd leave Florence in a car at your 2 PM (if you can't go sooner) and head straight to San Gimignano. You can spend a couple of hours there, climb a tower, walk the streets, then head on to Monteriggioni. This is a charming spot, but frankly you can pull up to near the center, walk around for an hour or less and you've pretty much "seen it". Then go into Siena for the night, when I think it's at its prettiest. In the morning head out to Montepulciano, stopping in Pienza. If you like you could go on to Cortona, as it's a pretty straight and quick shot back to Siena if you want to spend the second night there too. That way you'll be close to getting back to Florence in the morning.

I'd be flexible and if you get distracted in Pienza and Montepulciano, and if you stop in San Quirico on the way to those two (which you should), then just drop Cortona. Also you might want to take the "back road" from Pienza to Montepulciano going through the tiny but scenic town of Monticchiello.

I agree with others, you can see pretty much everything you'd want to in San G in a few hours, charming as it is, and that Siena is extra special after dusk.

NeoP offers a great routing suggestion.

Great advice. Good to hear that we can fit this much in. I appreciate the feedback because I had no idea how much to expect to fit in. We'll definitely be flexible in our schedule and if we happen to get sidetracked somewhere that's fine. I appreciate the help!

The more I think about it, the more I'd book two nights in Siena. That way you won't have luggage in your car all day the second day.

What do you think about leaving luggage in the car if it's in the trunk. Good idea or not really?

Well, we've done it a hundred times and never had a problem -- so long as it's not seen. And we don't park the car then stand there making a big deal about putting more things in the trunk and then locking it --announcing to the world "hey everybody, we're here locking all our valuables in the trunk so you can't steal it". That seems to be a common error.

We went in May a cpl of years ago and I was surprised at the huge crowds in every town visited. Its difficult to find a place to park in many of the more popular towns and with small winding roads, the going is slow. It was all well worth the waiting....just warning you that youll see fewer hill towns than you think in such a short period of time. Personally I loved Assisi.