Castello di San Fabiano

Monteroni d'Arbia, Italy

A historic brick castle with multiple towers and small windows, surrounded by greenery and flowers, under a cloudy sky.
Young woman in a black dress with fringe detail, holding a bottle of white wine and a clear plastic cup with beverage, smiling near a swimming pool with a historic brick building and lush green trees in the background.

Castello di San Fabiano is a historic castle in the heart of Tuscany's Crete Senesi countryside, about 15 minutes from Siena and surrounded by olive trees, pomegranate trees, and manicured gardens that look like a painting. This is not a castle-themed hotel. This is an actual castle, with actual history, actual puppies, and an actually somewhat active WWII bomb still lodged in the wall. More on that later.

QUICK INFO

Where?
Monteroni d'Arbia, Tuscany, Italy

Set among the rolling hills of the Crete Senesi, one of Tuscany's most beautiful and underrated landscapes. Siena is about 15 minutes away, and the castle sits at the perfect center point for exploring the broader region including Montepulciano, Pienza, and the Val d'Orcia. A car is essential and very much worth it.

Perfect for:
Couples, small groups of friends, and anyone doing a Tuscany road trip who wants a base that's actually memorable.

How many guests does this sleep?
Up to 4 guests across 2 bedrooms and 1 bathroom (but the castle has more rooms to rent!)

Services Included?
Daily housekeeping, homemade buffet breakfast every morning, WiFi, free parking, fresh linens and towels changed every 3 nights, complimentary toiletries, and a garden pool with hydromassage beds surrounded by pomegranate trees, olive trees, and roses. The hosts are included in spirit, and they are the best part.

Best way to get there?
Fly into Florence (FLR) or Rome Fiumicino (FCO) and rent a car. The castle is about an hour from Florence and two and a half hours from Rome. A car is non-negotiable here, and it doubles as your ticket to exploring the countryside properly.

Cost?
Check Airbnb for current pricing

A woman with short dark hair and tattoos on her arms, sitting at an outdoor table on a terrace with potted pink and red flowers behind her. She is wearing a black crop top and white pants, holding a cup of coffee or tea, with a sunny sky and tall cypress trees in the background.

Let me tell you about the kind of hosts Francesca and her family are. While we were exploring a nearby town, my friend chipped her tooth. Before we even had time to panic, our host had already called a dentist in the next town over who fixed it for free. That is the level of care and warmth you can expect at Castello di San Fabiano, and it set the tone for everything.

The castle itself is stunning in the way that only things with centuries of history can be. On our last day the hosts gave us a full tour and walked us through the entire history of the property. We saw a new litter of puppies living on the grounds. And then they showed us the WWII bomb that bounced into the castle wall and is still there, still lodged in the stone, and only "somewhat active" according to our hosts, who said it with the casual confidence of people who have lived next to it their entire lives. Truly one of the most unforgettable moments of any trip I've taken.

Every morning breakfast is served on the panoramic terrace overlooking the manicured gardens and rolling Tuscan hills. The spread is entirely homemade and local, fresh ricotta, pecorino, ham, house-baked bread, tarts, croissants, and jams made from fruit grown on the property. We sat there longer than we needed to every single morning because leaving felt wrong.

The garden pool is surrounded by pomegranate trees, olive trees, and roses, and has hydromassage beds built into the water. It is an absurdly beautiful place to spend an afternoon between day trips.

Use this castle as your base for a Tuscany road trip and you will not regret it. Siena, Montepulciano, Pienza, the Val d'Orcia, all within easy reach. Just watch out for the bomb.

Two women walking toward a medieval brick castle with a tower, surrounded by trees and a gravel path, under partly cloudy skies.
A woman in a black swimsuit is stepping into a swimming pool with inflatable floats and a beach ball on the side, surrounded by trees and outdoor furniture.
A courtyard with brick walls and arches, a stone fountain, a wheelbarrow, and a bench, with blue sky and clouds overhead.
A man in a light blue shirt and a woman with long brown hair exchanging a large, cylindrical object resembling a rocket or missile outside near a brick building with greenery.
A woman sitting on outdoor stairs with several dogs, some of which are in a gated area at the top of the stairs, with a brick wall on one side and a garden in the background.
Brick house with arched staircase, surrounded by greenery, under a partly cloudy sky.
An old stone well with a metal pulley system, a bucket hanging from the pulley, set against a red brick wall in a rustic courtyard.
A young woman with long blonde hair, wearing sunglasses, a black strapless top, black shorts, and sandals, stands smiling in front of an old building with a sign that reads 'POD S. SEBASTIANO'. The building has ivy growing over it and a rustic, weathered appearance.