Tucked between Montepulciano and Pienza, Lupaia is a tiny hamlet reborn — a hilltop cluster of stone houses surrounded by vineyards, lavender, and views that seem to soften the entire world. It is one of those rare places that strike you instantly: crafted, intimate, and deeply connected to the landscape.

Every space feels personal. Hand-painted walls, terracotta floors, fireplaces, soft linens, and terraces opening onto the Val d’Orcia create a feeling that goes far beyond a luxury stay. Lupaia is where discerning travellers come to slow down, savour Tuscan life at its gentlest pace, and enjoy a seamless blend of rustic character and refined comfort.

Travel planning

3  nights sharing a Suite

Daily breakfast

Fully comprehensive car hire arranged at the airport

We often pair Lupaia with Locanda al Colle for a journey that blends hilltop calm with sophisticated seaside living. Contact us to explore all the ways to combine this stay with other refined locations.

🌅 Self-Guided Excursions

• Panoramic circuit: Pienza, Monticchiello & the winding backroads of the Val d’Orcia

• Montepulciano wine route: boutique cellars & private tastings

• Bagno Vignoni: Roman thermal pools and slow-paced village charm

The most exclusive unit, offering a generous living area, refined Tuscan finishes, and a terrace overlooking the Val d’Orcia. Perfect for honeymoons.

Breakfast

A generous table served in the panoramic dining room: homemade pastries, estate eggs, seasonal fruits, cheeses, and warm dishes prepared to order.

Lunch

A relaxed, light menu featuring salads, vegetables, fresh pasta, and estate-grown produce.

Dinner

A nightly farm-to-table experience with a set menu that changes daily according to the garden and local suppliers — intimate, atmospheric, and deeply rooted in Tuscan tradition.

Dining Outside the Estate

Excellent trattorias and wine taverns in Monticchiello, Montepulciano, and Pienza — all within a short drive and ideal for variety on longer stays.

✔ Panoramic pool

✔ Gardens and walking paths

✔ Wine tastings and cooking demonstrations

✔ Outdoor terraces and lounge areas

✔ Concierge for experiences and tastings

✔ Air-conditioning

✔ Luxury toiletries

✔ Coffee & tea set

✔ Minibar

✔ Selected rooms with fireplaces

• Hilltop gardens designed for contemplation

• Sunset terraces overlooking layers of Tuscan hills

• Traditional stone architecture with contemporary artisan details

• Working vegetable garden supplying the restaurant

• Small estate trails for morning or pre-dinner walks

• Intimate scale — a feeling of being “in your own hamlet”

📍 Pienza: 10 mins — Renaissance architecture and panoramic walks

📍 Montepulciano: 15 mins — Vino Nobile cellars and noble palaces

📍 Monticchiello: 10 mins — Tiny fortress village with exceptional views

📍 Bagno Vignoni: 25 mins — Historic thermal village with hot springs

📍 San Quirico d’Orcia: 20 mins — Gardens, churches, and easy scenic strolls

📍 Montalcino: 40 mins — Brunello wineries and fortified walls

📍 Chianciano Thermal Baths: 25 mins — Spa day options

📍 Val d’Orcia panoramic drives: Immediate — arguably the best in Tuscany