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15 May 2025 by Meriel Lowe
I recently had the pleasure of staying at Castel Monastero, a destination I’d long known about but never experienced firsthand. The big question: would it live up to my dreams and expectations?
The journey to Tuscany
To reach this stunning retreat, I flew from London City Airport. It’s small but incredibly efficient – no long waits, and no buses to board the plane (it’s only about 15 meters from the terminal!). Just under two hours later, we landed in Florence, another small airport that’s quick to navigate. From there, you can easily either grab your transfer or rental car. In no time, I was off towards the heart of Tuscany.
The drive to Castel Monastero takes just over an hour. The road is fast and easy, making the trip feel shorter than it is. I got a glimpse of the towers of San Gimignano on a hilltop, followed by the walled town of Monteriggioni on the way. A few minutes later, the spires of Siena appeared in the distance. Then, a quick detour off the highway led me to Castel Monastero – tucked atop a hill, this 11th-century monastery-turned-luxury-hotel exudes charm.
Views from Castel Monastero
History meets luxury
Originally an 11th-century monastery, Castel Monastero was later purchased by a wealthy Siena family who used it as their summer residence. In 2009, it was converted into a luxury 5-star hotel, though with a delightful twist. The hotel is centred around a former village square, with many rooms overlooking it. During the warmer months, breakfast, dining, and the bar spill out into the square, and a couple of times a month, you might even catch live music or festivities. Oh, and if you're thinking of tying the knot, there’s a lovely chapel on the square, perfect for a unique wedding venue.
Castel Monastero dates back to the 11th century
The tranquil grounds
Beyond the central village, Castel Monastero’s estate expands further. A short, five-minute stroll down a lavender-lined avenue leads you to the pool area, where three sizeable pools are surrounded by parasols and sun loungers. Overlooking this serene space is the hotel’s Spa building, which also features guest rooms on its upper floors.
Refreshing pool at Castel Monastero
Relax and recharge at the spa
Speaking of relaxation, Castel Monastero is known for its extensive spa, with facilities including a Hammam, Finnish sauna, indoor pool, and an unusual saltwater pool. The high mineral concentration in the saltwater allows you to float effortlessly, leaving your skin feeling incredibly soft. After indulging in a blissful back and neck massage (though far too short!), I can confidently say the spa is worth a visit. In addition to massages, the spa offers health detoxes, weight-loss treatments and anti-aging programs.
Monasterii Spa
Rooms designed with charm and character
Accommodation at Castel Monastero comes in the form of rooms and suites, all uniquely designed within the constraints of medieval walls dating back to the 11th century. The lead-in rooms are very comfortable, offering views of either the countryside or the square, but, for those seeking something more spacious, there are large suites and even a private 3-bedroom villa. Since many of the rooms are located on different levels due to the building’s historical structure, I recommend mentioning if you have any mobility concerns when booking. If you’re a spa enthusiast, a room near the spa might also be worth considering.
Superior Room
Dining and drinks
The hotel boasts a lovely bar that feels like a cosy club in the cooler months, but once the sun is out, most guests prefer to imbibe on the terrace. There are also two restaurants to choose from, each offering exceptional cuisine. The Tuscan-inspired Cantina Restaurant is set inside former monastic wine cellars and also offers outdoor seating amidst flowers and olive trees. Then there’s the Contrada Michelin-star restaurant, helmed by chef Davide. Elegant yet comfortable, the five-course tasting menu is an absolute delight.
The hotel has a pair of restaurants – Contrada and Cantina
Peace, tranquility and activities
If relaxation and peace are what you seek, (they do have WiFi though) Castel Monastero is the perfect spot. Surrounded by green hills and complete tranquility, you can enjoy peaceful walks or simply unwind to the sound of birdsong. I took an easy, hour-long hike uphill through the woods and passed only two cars during my entire 3-4 mile wander. There are plenty of other hiking trails, plus a tennis court on the property. For something a bit more adventurous, the hotel can arrange activities like truffle hunting, cooking classes with the Michelin-star chef, or even a thrilling day driving a Lamborghini or Ferrari through the Tuscan hills.
Consider exploring Tuscany with a luxury sports car
Exploring Tuscany
As the hotel is remotely located and has plenty of parking, self-driving is to be recommended, and will permit you to discover other Tuscan gems, plus the neighbouring Chianti region, but as Siena is only a 20 minute drive away, this is an absolute must. It is a very attractive city, which of course buzzes in July and August due to Il Palio horserace (speak to us if this is something you would like to do). ‘Il Campo’ the main square is quite something else – and now, having been there 3 times, I would say never fails to impress. So, did Castel Monastero live up to my dreams and expectations? Most definitely. More than that, I yearn to return as soon as possible!
