Certosa di Maggiano: A Monastery’s Wild, Cinematic Second Life

Certosa di Maggiano sits just outside Siena’s city walls—close enough to feel connected to the city, far enough to feel like its own world. The property began in 1314 as a Carthusian monastery, and, after the order was dissolved in the late 18th century, the buildings became a small residential community, home to roughly 30 families living within the old walls. In 1969, Anna Ricordati fell for the property in its faded, half-ruined state and spent years acquiring it piece by piece, including two rooms still owned by the church, before restoring it with architect Renzo Mongiardino. It opened as a hotel in the late 1970s, becoming Italy’s first Relais & Chateaux property along the way, though that affiliation has since been dropped.

Fruit trees in the gardens

What actually sets the design apart is Mongiardino’s background in cinema. It shows. Rather than the restrained, neutral luxury look so many historic properties default to, Certosa di Maggiano is colorful, layered, and genuinely whimsical, with patterned walls, bold tiling, and mismatched prints sitting right alongside original frescoes and vaulted ceilings. It reads like a very well-traveled friend’s home more than a hotel, in the best way.

Sitting room

The property has 22 rooms across two sides—15 on the main side and seven on the other—including four ground-floor rooms. There’s no elevator, which is worth knowing for anyone with mobility concerns, since the third-floor rooms in particular tend to suit younger, more mobile guests. Every room has a walk-in shower, air conditioning, and a minibar. For families or small groups, four connecting rooms can be booked together, and the entire upper floor—all seven rooms—can be privatized for a group wanting full exclusivity.

Deluxe room

Cheeky bathrobe details

Outside, the grounds do a lot of the talking, with a medieval chapel, an 800-year-old magnolia tree, and olive groves that produce the hotel’s own oil. There’s a pool, tennis courts, and even a helicopter pad. The staff have a genuine, warm demeanor, and you can tell they have a true love for the property and for the guests.

Pool area

Certosa di Maggiano is best suited to couples and families looking for a base with real character rather than a predictable five-star formula, and it works especially well as a jumping-off point for the wider region, as Florence, Assisi, the Val d’Orcia, and Lake Trasimeno are all roughly an hour away. A car is genuinely worth having here. It’s a strong fit for slower, longer stays rather than a single overnight. High-season guests often stay a full week to 10 days.

Magnolia tree

• Breakfast is included with every stay, served from 7:30 to 10 a.m. in the courtyard or the indoor dining room.

• There is no elevator on the property, so ground floor rooms are the better call for anyone with mobility considerations.

• Pool day passes are available for non-overnight guests at €50 per person. Same-day reservations are required, which is a nice option if you’re staying nearby rather than at the property itself.

• A massage room is on site, with treatments bookable throughout the day.

• The property closes annually from mid-January through the end of February for renovations.

• Weddings are possible but require a full hotel buyout, generally around 50 guests minimum, and it’s not a space actively marketed for events during high season.

• Book well ahead if you’re eyeing a high-season stay, as the property sells out!

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