Rocca Di Castagnoli

Hotel Description

You know what struck me first about Rocca Di Castagnoli? It’s not just another hotel that happens to be in Chianti – this place actually feels like it grew out of the landscape. When you’re winding through those narrow roads around Gaiole in Chianti (and honestly, take your time because the views are ridiculous), you’ll spot this ancient stone structure perched on a hill that looks like it’s been watching over the vineyards for centuries. Which, well, it basically has.

The thing about staying here is that you’re not just booking a room – you’re stepping into what feels like a working piece of Tuscan history. The original castle dates back to the 1000s, and they’ve done this amazing job of keeping that medieval character while making sure you’ve got all the modern comforts you actually need. I mean, the stone walls are thick enough that you won’t hear your neighbors (always a win), and the rooms have this perfect balance of rustic charm and actual functionality. The 8.2 rating makes sense when you experience it – it’s not trying to be a flashy five-star resort, but it nails what it’s going for.

What really gets me about this place is how connected you feel to the whole Chianti experience. You’re literally surrounded by their own vineyards, and in the morning you can walk out and see the fog lifting off the hills while sipping coffee that actually tastes like Italy. The staff here – they know their wine, obviously, but they also know which back roads to take to Siena if you want to skip the tourist traffic, or where to find the best wild boar ragu in the area (pro tip: ask them). During harvest season in September and October, you can actually smell the grapes being processed, which sounds cheesy but is honestly pretty magical. The location in Località Castagnoli puts you right in the heart of Classico territory, so you’re not dealing with the crowds of some of the more touristy spots, but you’re still close enough to explore the famous wine towns when you want to. Parking’s easy here too – none of that stress you get trying to navigate medieval town centers with a rental car. I’d say if you’re looking for an authentic Chianti experience without roughing it, and you want to feel like you’re staying somewhere with real character and history, this is your spot.

Rooms

• Estimated price from: $234. Standard Apartment with 1 large double bed for Max persons: 2
• Estimated price from: $234. Standard Apartment with 1 large double bed for Max persons: 2
• Estimated price from: $351. Superior Apartment with 2 × 1 large double bed for Max persons: 2
• Estimated price from: $281. Two-Bedroom Apartment with 2 × 1 large double bed for Max persons: 4
• Estimated price from: $292. Two-Bedroom Apartment with 2 × 1 large double bed for Max persons: 4
• Estimated price from: $351. Two-Bedroom Apartment with 2 × 1 large double bed for Max persons: 4

Reviews

• Gorgeous lovely but need a car and expect to use it. – Lucy from United Kingdom – 9 July 2025 (7/10)

  The size the decor the ambiance and the bed comfort the location and view. Excellent breakfast. Wonderful restaurant.
  
  What could be improved: No facility for any snacks or lunch outside restaurant during the day which was too expensive for everyday . Needs a bar to serve the rooms and visitors. Pool could have been cleaner but a minor point.

• Idyllic place to stay! – Heather from Netherlands – 1 June 2025 (8/10)

  This was a magnificent castle! Such an exceptional place to stay. Restaurant and breakfast were excellent. The tartare and pasta with truffel were mind blowing! Staff was really friendly and helpful. Room was comfortable, well equipped and with a good shower. We loved staying here.
  
  What could be improved: Didn’t like is a bit harsh. Minor things that could be improved were that we thought the bed was a bit hard, there were no parasols by the pool and the ventilator from the restaurant’s kitchen was loud and was on until late in the evening. This kind of harshed our evening mellow.

• Lovely place to get away from it all – Tony from Ireland – 28 August 2024 (8/10)

  Lovely room, great facilities and location was fabulous.
  
  What could be improved: On the first night of our stay the restaurant was closed and the staff directed us to the only nearby restaurant saying we didn’t need a booking but it was booked out when we arrived.

• Beautiful vineyard with stunning views – Olivia from United Arab Emirates – 24 June 2024 (8/10)

  The location is absolutely beautiful and peaceful, with outstanding views. The room was spacious and had lovely views as well. The pool area was simply stunning.
  
  What could be improved: The breakfast was disappointing as options were limited and not replenished. It would have been a nice touch to have a bottle of wine in the room, especially considering it's a vineyard. My daughter stayed at a nearby vineyard that provided a half bottle of wine in the room, which I feel would have been a nice addition to our stay.

• Very good – Misty from United States – 12 June 2024 (8/10)

  Beautiful location and grounds. Breakfast was wonderful. We enjoyed the pool, tasting room, and restaurant.
  
  What could be improved: We did not have WiFi in our apartment during the stay. The roads leading to the property are very narrow and winding, making the trip from Florence a bit longer than expected.

• As we imagined – Joanne from United States – 15 May 2024 (8/10)

  Beautiful old buildings
  
  What could be improved: No clothes washing facilities and difficult roads for driving at night

• I Like this place – Tat from Thailand – 14 May 2024 (9/10)

  Location is beautiful. Staffs are nice.
  My room is big and very comfortable.
  Food is good.
  
  What could be improved: Room is not so clean, Wifi is not good.

• Amazing views in a quiet location – Beth from United Kingdom – 21 June 2023 (9/10)

  Beautiful views all around we had lunch at the restaurant which was amazing. Pool was quiet and a great place to relax.
  
  What could be improved: Furnishings are a bit dated and we couldn’t figure out the air con

• Superb – Nigel from United Kingdom – 11 June 2023 (9/10)

  Fantastic old castle, lots of character. Great restaurant (but you need to book) lovely location. Never felt crowded plenty of space for sitting and enjoying the view. Great for walking cycling and exploring. There are plenty of places to eat and drink nearby. Staff were friendly and helpful.
  
  What could be improved: It is quite remote so a car is almost essential if you want to explore the area. Taxis have to be booked well in advance if you are using them. The swimming pool was great but a bit cold in May.

• lovely getaway in the Chianti hills – Hristijan from North Macedonia – 8 June 2023 (8/10)

  wonderful remodeled/adapted village fortifications. rooms were beautifully adapted. decent rooms. reasonably comfortable considering the country setting. excellent restaurant on the premises open for lunch and dinner. Wine tastings organized on site (book ahead). insist on having Nicola as your sommelier, he’s both knowledgeable and a delight— he will make your day. Great wines to be had in this house.
  
  What could be improved: check in/reception staff can improve their game a bit. this is a big end place, guests expect a bit more.

SURROUNDINGS

Facilities