Siena or Castellina for two nights in Chianti region


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Hello! My five friends and I are looking forward to ten days in Tuscany in September 2024. We have three nights in Florence, then will rent a car and leave it at the La Spezia train station for a two night stay in Cinque Terre. Then we stop at San Gimignano (gelato and beauty) our way to the Chianti region for two nights. Then enjoy the views of Val'Orcia on our way to stay in Montalpulciano for two nights. Then drive back to Florence to return our car and speed train it back to Rome for our flight home.

I just can't decide if it would be easiest to stay in Siena and visit Castellina for a day trip or make Castellina the two night base and visit Siena one day! If we stay in Siena it might be easier with our car and more activity might be at our disposal, but if we stay in Castellina (Locanda Le Piazze maybe) we would enjoy the countryside. Help please! Thanks
That's a great itinerary! I understand your dilemma with choosing between countryside and city between Castellina and Siena.

Since you're coming in September, the weather is still great but fall is right around the corner, it's the season of harvest for grapes and grains. Since you're doing Florence, CT and then Montepulciano, I personally would go with staying in Castellina. The Locanda Le Piazze looks lovely, you would have a pool and great views. That area is very pretty, great views everywhere. We also like Romitorio di Serelle in that area and Il Cellese, take a look at those as well, La Rocca di Cispiano is also in the area but more rustic, while Relais Borgo di Pietrafitta is similar to Le Piazze (you can check them out here: . Depends on how luxurious you are feeling. Castellina will offer the pool and chance to experience the relaxing countryside experience... then I'd do a whole day in Siena (or late afternoon and evening), so that you can dinner Siena in the evening when most of the day crowds are gone. This way you do both. I love staying in Siena but in that period having the pool might also be very nice ;-).

For Val d'Orcia, I love the area around Pienza and San Quirico, but if you choose to stay in a town, Montepulciano would also be lovely. The Del Corto Suites are really nice - but the Stuart apartments also offer great views and the chance to have a kitchen to enjoy some relaxing meals "at home" -

Let me know what you choose, it's always great to see how itineraries turn out and know they work out!