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Last updated: 27 January, 2023
Expert travel writer: Nicky Swallow

This beautiful, stylishly-restored 17th century farmhouse complex has been turned into a luxury country retreat, hidden away down a long winding lane in the UNESCO-designated Val d’Orcia.

The 12 bedrooms – which size-wise are more like suites – inhabit the old stone farm buildings, and are done out in luxe-rustic style with massive beds, splendid bathrooms and private garden areas.

The heart of the hotel is the restaurant, with its open kitchen and vast fireplace; meals are served here in cooler weather, or on the romantic terrace decorated with fairy lights in summer.

Located in the heart of the Val d’Orcia, just outside Montepulciano, Lupaia makes a perfect base for exploring the area; Pienza, Bagno Vignoni and San Quirico d’Orcia are all within a 30-minute drive.

The owner-managers are always on hand and full of helpful advice about how to get the best from the area, giving the place a really personal, intimate feel.

It’s a great choice for couples and those who want to really immerse themselves in Tuscan life.

Surrounding area

The property is set in open, rolling countryside down a 2.5km unpaved road, that winds through olive groves and vineyards.

Views are of rolling hills dotted with cypresses and the odd mellow farmhouse, with Montepulciano across the valley. The soundtrack to a stay here is of birds and bees.

Montepulciano is a lively town with restaurants, cafés, bars and some good shops and a summer classical music festival.

While you're there

For all you foodies out there, the hotel offers several tempting gastronomic experiences you can sign up for – a cooking class (3-course Italian meal), a wine tasting, a sunset negroni experience and a truffle hunt (you get to eat the truffles after in a dish prepared by the chef).

You can also book onto a 4-hour guided e-bike tour with Andrea through beautiful Tuscan countryside. It’s a superb circular route, taking in the towns of Montefollonico, Pienza and Montepulciano (shorter, single-town options are available too).

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Key facilities

Airport transfers*
Beach: None
Fitness centre
Fitness classes
Golf course
Hot tub
Kids club
Parking: On-site (free)
Pool (adults only)
Pool (indoor)
Pool (outdoor)
Pool (kids)
Tennis courts
WiFi: Free

Food & drink

All inclusive
Kids menu
Restaurant on-site
Self catering
Additional charge

Room types


Room facilities

Air conditioning
Flat screen TV
Jacuzzi (private)
Pool (private)
Tea & coffee making facilities

Bedding options

2+ bedrooms
3+ beds
Connecting rooms
Rollaway/sofa bed

Bucket list experiences our writer says you must do in this destination, closest first

A day in the Val d’Orcia

Val d'Orcia, Tuscany, Italy[9.6 miles]

One of the most beautiful areas of Tuscany, the Val d’Orcia is a ravishing expanse of open, undulating farmland, dotted by atmospheric hill towns and dominated by Monte Amiata, an extinct volcano.

Best for ages: 18+ | Free

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Walk from Montalcino to Sant Antimo

Montalcino, Tuscany, Italy[22.5 miles]

A beautiful 3-hour walk (just over 8 miles) that takes you through farmland and Brunello wine country, passing old farmhouses and tiny stone hamlets that have remained unchanged for centuries.

Best for ages: 13+ | Free | 3 hours

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Other worthwhile experiences in this destination if you have the time or the interest, closest first

Abbey of Sant’Antimo

Abbey of Sant’Antimo

Castelnuovo dell'Abate, Tuscany, Italy[22.9 miles]

The beautiful Benedictine abbey of Sant’Antimo lies in open countryside close to Montalcino and dates from the 8th century; the resident monks sing Gregorian chants each evening.

Best for ages: 18+ | Free

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panorama of the Brunello wine lands in the spring with hills covered with soft green grass in the town of Montalcino

Montalcino Wine Region

Montalcino, Tuscany, Italy[22.9 miles]

Known for its highly-prized (and often expensive) DOCG Brunello wine, Montalcino is one of the most famous wine-growing areas in Tuscany. Many of the local wine estates are open for tastings; among the best are Casato Primedonne, Casanova di Neri, Biondi Santi Tenuta Greppo and Castello di Banfi. Visits must be booked in advance.

Best for ages: 18+ | Free

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Destination guides including or relevant to this place to stay


Tuscany, Italy

The astonishingly beautiful region of Tuscany has it all: art cities and ancient hill towns, high mountains and long sandy beaches, alongside luxurious hotels and some of Italy’s best food and wine.

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