Just finished typing this out at the request of my boss who is doing the above and asked for my recommendations. Thought I would share!

- go straight to the Duomo, it's one of the best. We also enjoyed the Duomo museum (Museo Dell'Opera) plus the panorama view. We thought the crypt was boring (no offence, if that's the kind of thing that interests you)

- You will likely come across Il Campo (the main "square" - it's not a square shape) several times. I would recommend stopping for a drink just 'cause it's cool. We have eaten at restaurants along the Campo twice out of necessity (looking for something fast and quick) and the food is mediocre. Can't beat the ambience though.

- we did climb the Campanile (bell tower) the first time. It took about an hour of waiting in line as they limit the number of people at the top at one time. The view was quite lovely but if you've had other lovely views of Tuscany, it may not be worth it if there is a line

- wander the streets (of course!)

- find a shop that sells a 1997 Cerretalto (Brunello) and drink it! Right there, probably. It was that good!

- we did go to the Fortezza and didn't think it was that exciting. Maybe we didn't quite get it.

- have a prosecco and a capuccino in a coffee/wine bar

- eat at: Trattoria San Guiseppe (1st choice), Osteria Boccon Del Prete (2nd choice)

I would add that visitors should seek out the Palazzo Pubblico to view the unique 14th c. fresco cycle that contains the Allegory of Good Government, the Effects of Good Government on Town and Country, and the Allegory of Bad Government (or the "Ill-governed Town and Country&quot painted by Ambrogio Lorenzetti.

And while in the Duomo, one should be sure to enter the Libreria Piccolomini.

The crypt may not be the most exciting place, but as it is included in the €10 cathedral, museum, baptistry ticket , it is worth doing.
The views from the campanile are excellent, but not too different from those from the panorama accesseed from the Museo del'opera (part of the combined duomo ticket).

My favourite places in the campo are the bars with outside terraces above the groud floor level - there is one in the bottom left corner (as you face the tower) another near the fountain. The drinks might be more expensive, but the views make up for it.

I'd be interested in what mode of transportation you've recommended the Boss use to get there....

I would go to the Campo late at night or early in the morning before the CROWDS are there.

Agree with the Piccolomini Library - I didn't think to specify that.

I've not been in the Palazzo Pubblico - thanks for the tip. I will add that to the list!

Agree that the views from the Panorama are similar to the Campanile. Perhaps I didn't specify that as clearly as I could.

PS: Dukey, my boss is spending a week in Florence and plans to drive to Siena for a day trip. He asked me for my list of what to do in one day.

Exactly the point---why drive, take the bus---more convenient.

Purple,

Back at the Duomo, in addition to the marvelous frescoes of the Piccolomini Library, it's worth noting the Bernini Chapel. Dating from the mid-17th century, this Baroque chapel is an absolute must-see, including the statues of Mary Magdalene and St. Jerome.

Having viewed the Chapel, Rick Steves was moved to
write, "(it's) enough to make even a Lutheran light a candle."

Best of luck.

I would say without a doubt eat dinner at "El Cano e Gato". I'm not a true foodie but it was without a doubt one of our best meals in Italy. Very memorable.

That and wander the neighborhoods a little to see the various "colors".

We loved Sienna.

Cheers, the turnip

Agree about taking the bus from Florence to Siena. It leaves from near Florence's main train station and drops you in the middle of old Siena. No worry about parking and finding your way, no worry about getting into town from the train station. And the bus is comfortable.

And the one thing I'd do in Siena-- short of attending the Palio--is stay overnight. All the tourists leave and it's very dark and medieval. It feels like you've time-traveled back 500 years.

Bookmarking

It is not really relevant to the original post, because of time restrictions, and much else to see.

If you had longer in Siena, then here is a silly thing to do: Siena is divided into 17 areas each called a contrada. Each has a church, a stable a museum and a fountain. Without studying a map, see how many you can find.