The rural Chianti is my favorite part of Tuscany. I stayed some days on a traditional farm with these typical Tuscan stone houses and vineyards. I loved it.
It is important to have a car so you can drive through Chianti, see the classic landscape, and visit some cute small towns. Avoid the highways and take the smaller roads for a more beautiful scenario.
I drove from SAN CASCIANO IN VAL DI PESA to SIENA and then MONTALCINO, through SR2 ROAD. The journey took about 1 hour and 30 minutes and was breathtaking, as expected.
There are many other stunning landscapes and towns around, such as PIENZA and MONTEPULCIANO.
You will also find wine tours so you can get to know the vineyards and production of the world-famous Chianti wines.
RESTAURANT RECOMMENDATIONS: my favorite was TRATTORIA DELLA FONTE for a perfect view and Tuscany experience. In second place LA CANTINETTA DI RIGNANA was also tasty and beautiful.
SIENA
Siena is well-known for its medieval landscape with its brick buildings, including the 17th century PIAZZA DEL CAMPO and PALAZZO PUBBLICO. The historic center is a UNESCO World Heritage Site. It is also known for its Palio Horse Race, which happens twice a year.
It is a nice day trip to do, and I would say the landscape I saw while driving was even better than the city itself.
Enjoy the narrow streets, restaurants, galleries, and some ice cream.