"It is rare that I take the time to post a review, but after staying at Castel Monastero, I felt compelled to do so. My wife and I recently stayed there on a vacation package that included the Palio di Siena. The Palio experience was awesome as we got to attend a communal dinner with one of the contradas and then watched the race from the comfort of an apartment (complete with refreshments) overlooking the track. While the Palio was an amazing event, so was our time at the resort itself. We found it to be such a lovely, charming place. If you are looking for a luxe resort full of modern amenities, this might not be the right fit for you (obviously the structures are rather old), but the property is breathtaking and we were quite comfortable nonetheless. Moreover, the service was exceptional and the staff was exceedingly helpful accommodating us even when we had to make last minute amendments to our plans. Overall we had such a wonderful experience and would strongly recommend it to anyone seeking a special getaway."

"I want to start by acknowledging the effort that went into a special birthday dinner during our stay — it was a genuinely lovely evening and one of the highlights of our trip. For that, real credit is due. Unfortunately, it wasn't enough to offset a long list of issues that, taken together, make it hard to justify this property's 5-star classification. In my view, this is a 4-star hotel at best. Staff & Service The property itself is beautiful and well maintained, but the service doesn't match. Staff often seemed overworked and under pressure rather than genuinely engaged,more like they were operating under a culture of fear than one of proper training and support. This is probably due to the two arrogant manager ladies browsing the property at all times and keeping everything under their evil eye. Requests were met with delays and a general lack of both proactivity and general sense: coasters and napkins weren't provided, drinks took a long time to arrive just in order to be spilled during serving. The poor staff on duty at the pool had to run through the heat carrying food from the kitchen to the pool because they weren't permitted to use carts. I actually feld bed ordering something. Simple requests, like finding a (high) table for a short bar reception or getting a straightforward wine recommendation, proved surprisingly difficult. Additionally there was loud American pop music everywhere. At the pool once I asked the music to be stopped because it was more like a disco. The staff wondered why .... Food & Beverage This is where the gap between price and value was most obvious. The advertised "show kitchen" BBQ turned out to be little more than premade pasta arranged buffet-style — a disappointing and overpriced setup for what's marketed as a tourist highlight. I give them credits for the BBQ itself which had three options: beef, chicken and sausage. What a wide range to choose from! And the sides, either vegetables or salad. How plentiful! Dessert options were limited to ice cream, which felt cheap for a property at this price point. The breakfast was fine considering it's Italy, where the breakfast culture is more an espresso and a sweet treat, it was acceptable. Charging separately for boiled eggs at breakfast was, frankly, absurd. Especially if it is 5€ for one boiled egg. Just makes me wonder ... a lot of luxury places charge for "elevated" eggs, but not a regular boiled egg ... The open sparkling wine selection was very limited, and it took nearly an hour of back-and-forth with staff who couldn't answer basic questions before a sommelier was finally called in to recommend a bottled wine. The wine list itself leaned heavily toward expensive imports (a €30 glass of French champagne, for instance) when, staying in Tuscany, guests are naturally looking for a strong regional Italian selection instead. On a positive note, the chef at the hotel's non-Michelin-starred restaurant (Cantina) was excellent — warm, personable, and serving what might be the best pasta I've had. Disappointingly, the same could not be said for the Michelin-starred restaurant (Contrada), where the chef came across as rude and declined our reservation. Rooms The rooms need real attention. There's no central light switch, the furniture felt worn and dated, and there's a lack of natural light. Most concerning, though, are the interior stairs in the rooms — the steps are steep and genuinely hazardous, even for someone young and fit. At minimum, the property should add guiding lights or reflective stickers for nighttime use, and ideally redesign the steps to be shallower or add a ramp. As it stands, this is a real safety concern. Also I experienced a glass that wasn't cleaned since the previous owner in the minibar, with lipstick on and an insect in the in-room-menu. Facilities The gym is under-maintained, with a dirty floor and not enough space to use the equipment comfortably. The pool area doesn't have enough sun loungers to meet demand. Overall The bones of a great hotel are here — the property is genuinely striking and well kept — but the price point promises a 5-star experience that the service, F&B offering, and room design simply don't deliver. Better staff training, more thoughtful pricing, and urgent attention to the room stairs would go a long way toward closing that gap. For now, I'd rate this a 4-star property charging 5-star prices."

"Beautiful hotel, delicious food, very attentive staff, relaxing spa, would absolutely stay again, highly recommended"