Only on this site
La Piazza
It opens onto the castle square: in the morning you wake up looking at the church, the walled gardens and the ramparts.
from €130 / night, breakfast included
Monteriggioni · between Siena and Florence
Sleep and eat inside a castle
Bed & Breakfast & Bistrot in an eighteenth-century house. Rooms and outdoor tables that look onto the castle square.
From €100 a night
Breakfast in your room, any hourOn the Via Francigena
Google 4.9 / 5
Tripadvisor Travelers’ Choice Award 2026
Why book direct
Only if you book here
Three rooms you won’t find on Booking or Airbnb. We keep them for people who come to us directly.
Inside the walls
The only place to stay on the castle square — where you never hear a car go past.
Breakfast at any hour
Warm bread and croissants outside your door by 6:30, and the fridge already stocked. The smell gets there before the alarm.
Free parking
Private, 300 metres away, with a permit to drive in and drop your bags.
Via Francigena
If you arrive on foot,
you sleep inside the walls
San Gimignano–Monteriggioni is thirty kilometres and eight hours of walking. When you come through the gate you have arrived: no outskirts to cross with your pack. We stamp your credential, warm bread is outside your door by 6:30 even if you leave in the dark, and you can drop your pack here from 8am.
Everything for walkersLuxury, to us, is warm stone at sunset, wine made by someone we know, and somebody who remembers your name.
Benedetta and Stefano, who run the Tenuta di Montechiaro wine estate together with their family, created Rooms and Wine: Bed & Breakfast & Bistrot. We are on the square of the Castle of Monteriggioni, in an eighteenth-century house standing on far older foundations, with a tasting room carved out of the oldest part of the building.
The same care goes into the room and into the plate: furniture salvaged and stood back up one piece at a time, vegetables and cheeses from family farms a few kilometres away, organic wine from the family estate. Plastic-free service, green energy and people from the village — not as a flag to wave, but because it is the simplest way to know what we are giving you.
“The care, the attention and the family feeling come back to us as very good reviews and a great many fond memories.”
Benedetta and Stefano
Our way of living in Monteriggioni
B&B&B
Bed
Rooms in an eighteenth-century house, looking onto the towers, the square or the Sienese countryside.
Breakfast
In your room, at whatever hour you like: warm bread and croissants from the village bakery, hung outside your door by 6:30.
Bistrot
A few seasonal dishes and our own estate wines, at the tables out on the square, at the foot of the towers.
A day here
Inside the walls,
the day has a shape
It isn’t only about where you sleep. It’s what you hear, smell and taste from waking up to goodnight, in a village where you never hear a car go past.
6:30
Bread at your door
No breakfast room, no sitting. Outside your door there’s a paper bag with bread still warm and croissants, and the fridge is already stocked. The smell gets there before the alarm does.
10:00
Morning quiet
Inside the walls you never hear a car go past. Before the coaches arrive there is only the sound of footsteps on stone, the swifts above the towers and the church bell.
17:00
A glass, no hurry
The afternoon is the square’s best hour: the stone is warm, the parasols throw a wide shade, and you can have a glass without staying on for dinner.
20:30
The stone catches fire
At sunset the walls turn from gold to pink. The tables stay outside, the village empties out, and the candles become almost the only light besides the windows.
23:00
The village is yours
Once the last car has gone out through the castle gate, Monteriggioni belongs to the people sleeping in it. That’s the moment you understand why you wanted to be inside the walls rather than outside.
Who welcomes you
A family,
not a front desk
Rooms and Wine belongs to Benedetta and Stefano, who with their family also run the estate the wine comes from. There is no booking office somewhere else: if you write, one of those two people answers.
In the room and behind the counter you’ll find Francesca and Maurizio, who will tell you what you’re drinking — even if you know nothing about wine, and especially if you know nothing about wine.
Benedetta · Stefano · Francesca · Maurizio
Bed & Breakfast
Rooms inside the walls
Three floors, three ways of being in the castle: the first with terracotta floors and exposed beams, the second with vaulted ceilings and the largest rooms, the top one — the highest floor in the castle — with uninterrupted views over the countryside. Wi-Fi, air conditioning, a mini fridge, a coffee machine and a kettle, and free private parking: in every room.
Only on this site
La Malvasia
Named after one of our wines — as particular as the room itself.
from €130 / night, breakfast included
Only on this site
Il Vicolo
Named after the lane it looks onto. Set at the back of the house, it is the quietest of them all.
from €130 / night, breakfast included
Wine Bistrot
The liquid soul
of Rooms and Wine
On the ground floor, opened in 2025 in the oldest rooms of the house. Here wine isn’t a footnote: it’s where the cooking starts. A few seasonal dishes — a tall, crisp pinsa, the pecorini and oil-cured vegetables of the Tuscan plate, one hot dish off the blackboard — and the tables outside, on the square.
Recommended by Restaurant Guru 2026
for the food, the wine list and the welcome.
Wine tastings
Six tastings,
one landscape
The wines of our family estate, Montechiaro, and of two small organic growers we count as friends: the dark Sangiovese of the Colli Senesi, the taut Vernaccia of San Gimignano, the Vinsanto at the end. Every tasting is talked through at your table by one of our team, with a board of local food beside it.
Un Assaggio di Montechiaro · 2 glasses€15
I Classici ’345 · 3 glasses€20
Sfumature di Bianco · 3 glasses€20
Vini d’Autore · 4 glasses€25
Un Assaggio del Territorio · 4 glasses€25
La Scoperta del Sanguis Jovis · 4 glasses€30
The Wine Dinner · house guests only€45 / €50
L’Attico
Our
living room
On the top floor, under the old beams, a large room with terracotta floors and windows onto the countryside. An extra sitting room for our guests: read, have a coffee, watch the hills change colour as the evening comes down.
Where we are
In the middle
of Tuscany
The castle of Monteriggioni sits on the Via Francigena, halfway between Siena and Florence. From here the whole of Chianti is under an hour away.
15 minSiena
45 minFlorence
25 minSan Gimignano
300 mPrivate parking
Wine BistrotPiazza Dante Alighieri 15 — on the castle square.
Entrance to the roomsVia Ava dei Lambardi 1 — round the corner, on the lane. The building stands on the corner between the square and the alley: two doors, one house.
If your sat-nav still says Piazza Roma, you are in the right place: that is the old name of the same square.
Useful to know
Before you arrive
Check-in & check-out
Check-in between 3pm and 7pm, with self check-in if you’d rather. Check-out by 11am.
Breakfast
Served in your room. By 6:30 the baker leaves bread, croissants and a filled roll at your door. Vegetarian and gluten-free options on request.
Parking & restricted zone
Griccioli Private Parking, free, 300 metres away. Give us your number plate at online check-in and we’ll arrange a permit so you can drive up and drop your bags at the door.
On the Via Francigena
The castle is a stage on the pilgrim route. If you set off early, breakfast is already in your room from the night before and the bread arrives by 6:30: you walk out of the village gate with your pack, without waiting for anyone.
Concerts on the square
In high season, usually one evening a week, the square hosts a concert or a piece of theatre. You can watch it from your window, and it is all over by midnight. The calendar is on monteriggioniturismo.it.
For our guests
10% off dinner at the Wine Bistrot, and half-price afternoon tastings.
Reviews
What our guests say
★★★★★
“Passing through as pilgrims on the Via Francigena, we allowed ourselves this luxury — both for the night and for dinner. Breakfast is served in the room from 6:30, so you can set off early.”
Laura Q · Tripadvisor, July 2026★★★★★
“In the morning a paper bag is left hanging outside the room: fresh rolls, butter, jam, little apricot tarts, croissants to fill… wonderfully fragrant.”
Davide F. · Tripadvisor, January 2026★★★★★
“Our family has one celiac and another member with various food sensitivities, and the hosts were extremely knowledgeable about exactly what was in the food they served in the bistro and for breakfast. The modified menu items didn’t feel like compromises.”
Ryan and Zora S. · Tripadvisor, June 2026★★★★★
“You can see the passion and care the owners have put into the furnishings: every detail is thought through.”
63Cri63 · Tripadvisor, July 2026★★★★★
“We slept really well. The view of the town walls from the window: stunning.”
Marcello V. · Tripadvisor, November 2025★★★★★
“Francesca told us the story of the wine we were about to taste, so that even we, complete beginners, could appreciate its nuances.”
Denise P. · Tripadvisor, August 2025★★★★★
“The triple room was spacious, clean, quiet and with a lovely view. Breakfast served in the room, and parking just outside the walls.”
ciX m · Tripadvisor, June 2026★★★★★
“Great rooms, kind and very helpful welcome. It feels like a place out of this world — I wish we had stayed longer.”
Marco B. · Tripadvisor, April 2026★★★★★
“A truly central position, with a fine view over the main square. The building has been restored with care, while respecting its original structure.”
Myriam B. · Tripadvisor, April 2026★★★★★
“The ribollita and a Tuscan craft beer: all excellent, and the friendliest service.”
giovanniRoma · Tripadvisor, March 2026
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Life in the castle,
day by day
The seasons, the dish of the day, the bottles just opened and the square at eight in the evening.
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