After spending 20 years coming to Pienza on daytrips and gazing longingly over the "balcony" of the…read moresteep bluff into the Val D'Orcia, we decided to treat ourselves to a night here so we could even longer gazing over the incredible view.
Relais Il Chiostro was indeed a treat: A beautiful hotel right in the center of the old renaissance town with great amenities and a killer view. Although the hotel may be prominent on the Pienza skyline when viewed from the valley below, the entrance within the city gates is pretty demur, tucked obliquely between the Duomo and a gelato store. As the name implies, the hotel occupies the (renovated) space of the old convent and cloisters. Rooms each have a bed space, a small sitting suite and a bath. They're well-appointed with modern amenities.
Given the building's original purpose, each room is slightly different in configuration, and long-time returning guests apparently have their favorites and request those well in advance. Be sure to use the website to request a room that overlooks their outside yard and the stunning view of the Val D'Orcia below. (if ever there was a hotel that proved E.M. Forster's premise of asking for a "room with a view", this is it....the Mother of all Views.)
The hotel boasts an upscale restaurant, a pool overlooking the valley, and a wonderful yard which can be used for drinks, breakfasting or just mere awe-struck gazing. Staff are polite, and moderately helpful; some are even cordial. This town was explicitly rebuilt by a renaissance pope to be an artistic tourist attraction, and this remains true today. The old part of town can get mobbed during the day, so the somewhat jaded attitudes of the locals are understandable.
I booked well in advance, and actually found the price for a very nice room to be completely reasonable. I've paid more at Marriott Suites in the deep Midwest. I'm sure there are even more upscale rooms to be had here, but for what we got I couldn't be more pleased. I'd eagerly stay there again if I wanted to linger in Pienza overnight.
Two other quick notes:
--The old city is small, and is an "area pedonale" (pedestrians only.) This means you'll need to park your car elsewhere around Pienza. We dropped off luggage at one of the city gates about 200 yards from the hotel, and then went to find parking. Not always easy in such a crowded town. I'd suggest the large lot about 400 yards further down SS 146, across from the COOP. I also understand the hotel can issue you permit parking for an additional fee...might make some sense.
--Given the relative compactness of the old town, the number of restaurants is limited. They appear to try to stagger their "nights off". If you want to dine "in town", best to check with the hotel to find out what's open on any given night, and get a reservation, since space gets limited. (You'll also get better restaurant service, I've found.) Outside the old city walls, there also are some serviceable tourist-level restaurants, if you don't want the hassle of playing "hit or miss" in the old town.