We spent a week here in June and can't wait to return. It was a truly special time. The room - yes, a little tired, and the bathroom was small, but not a problem unless you need US style space - but it was really all about the view, which on first sight just takes your breath away. The place is very special - location, staff, food, wines ... Breakfast, and indeed dinner, on the terrace overlooking the valley was an experience we looked forward to every day. We loved the fact that the hotel is not shiny and new inside: character is so much more memorable than the bland uniformity of some more swish establishments. The other very special element is the staff, who were attentive, helpful and generally delightful. We were offered help booking visits to vineyards, hiring bikes and were given some wonderful recommendations on restaurants to try when out and about. I sincerely hope Il Chiostro doesn't get bought up and 'smartened up'. We love it just as it is.

Just spent 3 nights in Pienza at this special hotel and it was lovely. We travelled there with our 20-week old daughter and the staff was wonderfully accommodating. The room we stayed in (104) was a bit tired; however, it was clean and provided a beautiful view of the Val d'Orcia. The bathroom was probably the biggest disappointment, as the toiletries were basic, the drain to the shower was very slow and flooded the bathroom (it was a wheelchair accessible room, so no "curb" for the shower stall), and there was not much in the way of counter space.
We spent a good amount of time by the pool, which was lovely but nothing special. I think this has been a very dry year in Tuscany and the garden reflected the lack of rain (no big deal just not a wow factor). The breakfast was a nice continental breakfast, nothing particularly special; although, some of the best cappuccinos I have tasted where here! The view from breakfast IS special -- easily can spend lots of time sipping coffee and staring out at the horizon. The staff happily obliges -- no pressure to speed up your leisurely breakfast.
The people that this property attracts are a draw as well...it seems. We met some very interesting folks and everyone seemed respectful in the common spaces.

A beautiful building in an excellent location which did not completely live up to its expectations. It was reasonably cheap to stay here and as such, was very good value but some aspects of the room could have been improved - such as doors which did not lock properly and very little space for clothes.I booked a Junior Suite ( Not a good description as it was quite cramped) which was adequate but neither spacious nor luxurious which is a shame as the property has the potential to be amazing. I do not want to sound too negative as it was still very nice in some ways but I would describe it as 'cheap and cheerful' certainly not a true 4*. The location was ideal for looking around Pienza but be warned that finding a parking space is not always easy. A good base from which to look around the surrounding area and also to cycle from. Somme really good restaurants within walking distance.

I travelled with a friend and we stayed for 10 days in early September. We both kept saying how it was the perfect place to visit with our respective partners as Tuscany in general and the hotel in particular was ideal for a romantic break. We understood September was a good time of year for good weather and fewer crouds, and it proved to be so. The hotel Il Chiostro has a kind of faded grandure, and we felt we had stepped back in time. I would recommend booking a 'valley view' room. Which not only looks out over the Val d'orcia, but also the garden. We blew the budget and ate in the hotel restaurant several times because the food was so good. Eating outside was a particular pleasure as the terrace was beautiful at anytime of the day. Breakfast was excellent and the staff charming and helpful. A word of warning. Don't try having a nap around 6pm. You are staying in a converted monastery which still has a 'bell tower', complete with bells which ring out daily at 6. For us, this added to the charm. Pienza is a lovely, tranquil place, which is ideal if you want to relax and soak up the atmosphere. We did a trip to Florence by train, which was worth doing, but we were more than happy to get back to the Il Chiostro for some peace and quiet. Something to bear in mind is that while the hotel will park your car for you. This is an expensive option. Ok if you have just arrived and need a night to get your bearings though. There is free parking outside of the town walls. This works fine once you have found your way around a little.