5 nights in Tuscany: Montepulciano vs. San Quirico d'Orcia
 

which would you choose for a 5-night base in Tuscany, and why?

and, more specifically:

Hotel Palazzo del Capitano vs. La Locanda di San Francesco vs. Politian Apartments

thanks.

Personally, I would choose the Politian Apartments but that is our travel style--more room, easier to have casual meals and Giacomo (the owner) is a gem. Montepulciano is a delight and the Locanda di
San Francesco is first class in another very scenic position. Montepulciano is a very good base with lots of options for wines and restaurants.
I have not stayed in San Quirico but the Hotel Palazzo is well thought of and depending on your interests, a very convenient location with closer access to the traditional road trips to the Crete Senese, Pienza and Montalcino (Brunellos).
You won't go wrong with any of these options and FWIW, Montepulciano is a "steep" town while SQ is flat.

I have stayed at Capitano in San Quirico and visited Montepulciano.......both are very nice towns. Mac makes, to me anyway, an important distinction....San Quirico. is flat...easy walking, parking, etc. Montepulciano is indeed hilly...right through the middle of town

We've stay at La Locanda di San Francesco twice (October). Our rooms had views of tile roofs stepping down the hill to the plain below and Lake Trasimeno in the distance. You can't get that in a flat town. We enjoyed wine in the late afternoon on the outdoor deck with its views in the opposite direction. The owners offered great local info and restaurant recommendations.

On our visits to SQ, the town was very quiet, the opposite of Montepulciano which was fairly lively all day and through the evening. SQ is on the pilgrimage route Via Francigena and the route of the historic Mille Miglia auto race (Brescia-Rome-Brescia).

We have stayed in both La Locanda di San Francesco and Capitano in San Quirico on different trips. Although both are lovely, I would choose La Locanda di San Francesco as it is more lively at night with more choices for dining and enjoying strolling after dinner as Jean stated. Love Pienza and Montalcino as well~great day trips. If you are driving at night after dinner on a return to San Quirico, the roads are very curvy on a two lane road!

I've stayed in both towns and both are pleasant though Monte is bigger with more tourists about and steeper. So it depends on what you like. Stayed in Pienza and the views of Monte from Pienza are very nice especially at night (not so good the other way)

Big difference !
SQ is a small village whereas MP is at least 12,000 people.
Also, SQ is very flat but MP is very hilly.
SQ is more central for touring and easy to park a car. I would choose it for that reason.