Castelli del Chianti

Hotel Description

You know what? I’ve stayed in a lot of places in Tuscany, but Castelli del Chianti on Via Michelangelo Buonarroti actually gets it right. The location in Gaiole in Chianti is perfect – I mean, you’re literally in the heart of wine country without being stuck in some tourist trap. When you pull up, there’s decent parking (which, honestly, is half the battle in these hill towns), and the building itself has that authentic Tuscan stone thing going on without feeling like a theme park.

The staff here actually know the area – like, really know it. They pointed me toward this tiny enoteca about ten minutes away that I never would’ve found otherwise, and when I mentioned wanting to avoid the Chianti Classico crowds, they steered me to some smaller vineyards that were incredible. The rooms are what you’d expect from a solid 4-star place, but it’s the little touches that matter. The beds are properly comfortable (not always a given in historic buildings), and the bathrooms are updated without losing character. I stayed in September, which is prime harvest season, so there was this amazing energy in the town – you’d hear tractors heading out to the vineyards early in the morning, and honestly, it added to the whole experience rather than being annoying.

What really sets this place apart is how it connects you to the region. Gaiole isn’t Florence or Siena – it’s a working wine town where people actually live and work, not just pose for Instagram. The hotel feels like part of that community rather than some isolated resort bubble. Breakfast was regional stuff done well, and they don’t rush you out if you want to linger over coffee and plan your day. The concierge (well, I think that’s what she was) helped me book a last-minute tasting at Castello di Brolio, which was supposedly full – apparently they have relationships with the local estates that actually matter. Walking around town in the evening, you’ll find a couple of solid restaurants within easy walking distance, and the hotel staff will tell you which ones are worth it versus which ones are just coasting on location. I mean, that 8.9 rating makes sense when you experience the whole package – it’s not trying to be the fanciest place in Tuscany, but it delivers on what matters when you’re exploring wine country. The Wi-Fi works, the shower pressure is good, and you wake up feeling like you’re actually in Italy, not some sanitized version of it.

Rooms

• Estimated price from: $82. Double Room with 1 large double bed and 2 single beds for Max persons: 2
• Estimated price from: $79. Quadruple Room with 2 × 1 bunk bed, 1 large double bed and 2 single beds for Max persons: 2
• Estimated price from: $84. Double Room with 1 sofa bed and 1 large double bed for Max persons: 2

Reviews

• Exceptional – Vanessa from Brazil – 15 June 2025 (10/10)

  The place is new, very comfortable, with everything you need to an excellent stay. And Sophia is so so kind and helpful. We loved our stay there.

• Exceptional – Niamh from Ireland – 1 May 2024 (10/10)

  The visit was exceptional in every way
  Exceptional courtesy, wonderful bed, wonderfully planned fit out & the location itself was perfect.
  The facilities were first rate & everything suggests I choose this property every time I visit the whole area
  
  The most impressive, professional planning & even though I was there a short time I received the same level of courtesy as if I were staying a month. This aspect of the stay, in my view outlines exactly how wonderful the experience was
  
  The balcony area was a fantastic idea & truly ideal for lunch & dinner.
  
  A hearty tank you to my hosts 😊
  
  What could be improved: Absolutely everything.
  What was exceptional was the bed & shower but honestly the balcony & kitchen too. I experienced true rest & was very very refreshed the next day each day
  The photos on booking don't even do the place justice. It was a perfect experience.

• Exceptional – Dimitar from United Kingdom – 14 September 2023 (10/10)

  It was a wonderful place to stay in. Very modern in layout and functionality. 5 mins walk from the central square. The room is comfortable with a private bathroom, terrace, and many other perks. There are electric shutters that allow natural daylight in, but can also help one sleep in complete darkness if desired. The bed is really soft as if sleeping on a cloud. The service was very friendly and professional. I would definitely stay in Castelli del Chianti if I had another visit to Gaiole.

• Comfortable room, clean and good location. – Tiago from Portugal – 25 March 2025 (7/10)

  New, clean and large room
  
  What could be improved: The access door was a gate, not a proper entrance hall.
  The house is next to a Municipality kind of deposit for vans, cars and some other waste.

• ok for a short stay – Dirk from Germany – 30 October 2023 (7/10)

  very clean and conveniently located. I was there for L'Eroica. The appartment is very conveniently located on the border of the village. I had a small balcony. Very friendly and helpfulll people with an office in the basement of the house.
  
  What could be improved: its not very charming. Cold, white lights. A modern – no fuzz – clean and small appartment. Some people may like this.

• Superb – Enrico from Italy – 4 July 2025 (9/10)

  Posizione estremamente tranquilla, personale assolutamente cortese e disponibile, alloggio moderno e molto pulito, comodo parcheggio interno per le motociclette.

• Ottimo soggiorno nel Chianti – Federica from Italy – 29 June 2025 (9/10)

  Buona posizione vicino al centro di Gaiole e parcheggio gratuito di fronte alla struttura. Camera spaziosa, come anche il bagno, doccia grande. Balcone con tavolino dove fare quattro chiacchiere. Tutto molto pulito, nuovo e set di cortesia superfornito.
  Tutto perfetto. Se sarò in zona tornerò sicuramente.
  
  What could be improved: Niente

• Superb – Simone from Italy – 6 June 2025 (9/10)

  La proprietaria gentilissima e precisa nelle informazioni, struttura pulita, ben curata e parcheggio interno per le moto.

• Personale premuroso, buona posizione per vedere le bellezze del luogo, appartamento pulitissimo. – Paolo from Italy – 5 June 2025 (9/10)

  Personale premuroso, ottima comunicazione e consigli sui posti dove pranzare. Posizione ottima per fare l’Eroica.

• Superb – Sosio from Italy – 4 June 2025 (9/10)

  Posizione ottimale in Gaiole. Appena fori dal centro che comunque è raggiungibile in non più di 10 minuti a piedi.
  Viaggiando in moto ho trovato molto comodo il parcheggio interno alla struttura chiusa con cancello, la camera prevista di bel balcone ci ha dato la possibilità di lasciare gli indumenti tecnici e gli stivali all'esterno così da non insudiciare la stanza. Pulizia al top, personale gentile e premuroso nel venire incontro alle problematiche.
  Torneremo sicuramente.

SURROUNDINGS

Facilities