I just spent 6 days at Castle Montegufoni and it was a fabulous 5-star experience! You have to know It is not a hotel ( no room service) - it is truly a real castle, although has totally updated bathrooms.
ps. bring mosquito apartments, so you can also prepare your own things. (why? You're in Italy!!) I stayed in #22, a perfect apt for 2 that overlooks the main courtyard - I loved it. But you can also ask for an apt that overlooks the incredible landscape. There are also apts that aren't in the castle, but on the castle grounds- ask for what you want in size and location, there are choices!
The staff is friendly and helpful and can't do enough for you. They are also helpful in giving suggestions on places to go and see.
The food is clean, fresh from the area and both the food and wine was amazing.
My favorite part is the luscious landscapes you see from anywhere you look.
Walks / runs are something you will experience no where else. You can drive to the small towns and enjoy true Italian living with the locals.
There are interesting and fun vineyards to experience the locals wines, truffles, olive oil, and saffron.
Walk around the castle, the grounds are enormous, and check out all the unusual parts to the castle.
The reception staff isn't there all night, but you have a key to come and go.
Check the hours for the restaurant ( amazing!) , so you can plan when to eat there on the beautiful dining courtyard vs going out and exploring in the nearby nearby towns.
ps. bring mosquito lotion. I'm always chewed up - and I didn't get a single bite with mosquito lotion.
ENJOY- you will LOVE IT!