My husband is teaching wine marketing in Siena for University in USA. There is a 7 day break between terms. We are looking for a nice relaxing place to get away to during break for 4-5 days. We don't want to travel more than 2 hours,must have air conditioning and good food. Any suggestions. We are in Siena 6/18 till 9/15 so would like a nice break. Hopefully not more than 350,00 per nights
I used this tool:
https://www.freemaptools.com/radius-around-point.htm
Orvieto is in range, as is San Gimi, Florence, Pisa, Lucca, Livorno, Arezzo, Grosseto, and a lot of the Tyrrhenian Coast. If you wanted to stretch it a bit, you could go to 5 Terre. Or you could tour around Tuscany.
Villa Monte Solare may match your criteria and budget. It's a beautiful restored estate villa near Lake Trasimeno with an excellent on-site restaurant and great amenities - e.g. pool and spa (not sure if they still offer occasional evening concerts in the chapel). You could also easily do some short day trips to interesting towns and sights nearby. They have an excellent website, including a Google maps link that will allow you to see the location and estimated driving time from Siena.
Agriturismo Niccolai. They have three villas, and Villa Arnilu has individual rooms to rent. If you rent one get one with a view across the vineyards to San Gimignano. Niccolai has a winery and vineyards. I like their vernaccia.
You are close to Siena, very close to San Gimignano, within striking distance of Certaldo, Monteriggioni, and Volterra. You are an easy train trip from Poggibonsi to Florence.