Olga Modjaro, a travel blogger and writer, had loved Italy all her life and once planned to move there. But one day everything changed. For the past four years, she has been living with her family in France, in Burgundy, at the very heart of the famous wine town of Chablis.
Specially for Locals Insider, she has curated a selection of the best vineyard hotels in Tuscany, perfect for a wine-focused escape.
In October, Tuscany feels calm and secluded. The hills are painted in soft autumn tones, meadows are covered with fallen leaves, and ancient borghi appear especially quiet. It is the perfect time for slow, unhurried walks.
At agriturismos, seasonal dishes are served, while wineries continue open-air tastings among terraces and gardens, filled with crisp autumn air. From Chianti to Bolgheri, from Scansano to Montepulciano and Montalcino, each area preserves its own history and winemaking traditions.
Ancient borghi scattered across the Tuscan countryside retain their timeless charm. Some have been transformed into stylish wine resorts or alberghi diffusi, meaning scattered hotels made up of small apartments or rooms spread throughout a historic village or borgo. Others remain home to just a handful of residents living in harmony with nature.
Small agriturismos offer guests the chance to experience authentic Tuscan life, feel genuine hospitality, and stay closely connected to the surrounding landscape. What unites these places is wide-open panoramas, centuries-old olive groves, and an enduring respect for regional traditions.
Il Borro Relais & Châteaux
Il Borro is set on a rocky outcrop in the Upper Arno Valley, between Florence and Arezzo. Its stone buildings are surrounded by hundreds of hectares of land, much of it devoted to vineyards. Walking through the village feels like stepping back in time.
Every corner carries a story. The hamlet once belonged to the Medici family, later to the House of Savoy, and in 1993 it was restored by the Ferragamo family. Past and present intertwine here, along stone streets, historic workshops, and quiet piazzas where time seems to slow.
Rooms and suites, decorated with wood, natural fabrics, and understated classic details, blend seamlessly into the spirit of the village. There is the historic Dimora Storica villa for events, private villas Casetta and Mulino, and the Viesca estate. Each residence has its own atmosphere and distinct character.
One of Il Borro’s defining features is its community of artisans who continue the traditions of historic workshops. The estate is also home to La Corte Spa, offering treatments based on local olive oil and grape extracts. Two restaurants, Il Borro Tuscan Bistro and Osteria del Borro, serve dishes made with ingredients from the estate, balancing rustic simplicity with refined elegance.
As you wander between ancient buildings, shaded lanes, and open piazzas, you feel a harmony of nature and history, where every detail reflects centuries-old Tuscan traditions.
Lupaia
Set among the hills of Torrita di Siena, between the Val di Chiana and Val d’Orcia valleys, the charming Lupaia estate lies at the heart of Tuscany’s “wine triangle.” It is surrounded by renowned wine regions, including Vino Nobile di Montepulciano, Chianti Classico, and Brunello di Montalcino.
Originally a farmhouse dating back to 1622, it was lovingly transformed by Austrian couple Heidi and Christopher Müller into an intimate countryside retreat. The property offers just twelve rooms and suites housed in five historic stone and brick buildings, all draped in ivy.
Each room has its own personality. Some feature soft upholstered headboards and canopy beds, others lean toward rustic or refined Provençal styles. Every space invites rest and tranquility, allowing guests to choose the atmosphere that resonates most with their mood.
The grounds are filled with secluded corners for relaxation, whether it is resting in a hammock beneath the trees or enjoying a chilled glass of wine in the winter garden. Meals bring everyone together in the warm, homelike dining room, whether for breakfast, lunch, or dinner.
Wine lovers are drawn to the Stanza del Vino, or Wine Room, where tastings of local wines take place, from biodynamic Chianti to bold reds from Bolgheri. For those eager to explore new flavors, the estate offers workshops on making traditional Tuscan pici pasta, as well as guided walks with Caterina Cardia, an expert in wild edible plants, who generously shares her knowledge of local flora.
Here, it is impossible to feel idle. Every moment is filled with calm, aromas, and authentic Tuscan life.
Il Falconiere
In Tuscany, rolling hills and tiny villages never fail to inspire awe, and Il Falconiere feels like stepping into a world shaped by Silvia Baracchi, its owner and Michelin-starred chef. This sanctuary, without exaggeration, is set in gentle foothills at the base of Cortona and surrounded by thirty hectares of vineyards managed by the Baracchi family.
Wine has been produced here for five generations, dating back to 1860, when the family first planted vines on the sunlit slopes of the Val di Chiana. The estate resembles the setting of a Tuscan fairytale, with historic buildings including a chapel, a noble villa, and a farmhouse, along with two swimming pools and a spa, all immersed in the scents of rosemary and lavender.
Rooms and suites are scattered throughout the estate, each with its own character. Soft pastel tones and hand-painted details by local artisans create the feeling of a miniature dollhouse. Some rooms offer views stretching all the way to Monte Amiata.
The heart of Il Falconiere is its restaurant, housed in a glass conservatory with wrought-iron chairs and ceramic details. The setting is designed to create a memorable dining experience. Silvia’s cuisine is a playful interpretation of Tuscan traditions, while wines are poured directly from the estate’s vineyards.
A glass of Baracchi Brut Trebbiano Metodo Classico becomes a symbol of the chilometro zero philosophy and more than 160 years of family winemaking history.
La Fornace
La Fornace is a true country home, perched on a sunlit Tuscan hill and combining warmth with contemporary style. Gardens, lavender fields, and silvery olive groves surround the villa, while its terraces open onto sweeping views of rolling hills. It is an ideal setting for both quiet retreats and gatherings with family or friends.
The charming village of Montisi is just a short walk away, while easy access to Montalcino, Siena, and Florence makes it simple to explore Tuscany’s cultural and gastronomic heritage. Interiors are bright and spacious, with arched passageways, stone floors, and open-plan living areas. These spaces flow naturally onto terraces, ideal for alfresco dinners or sunset aperitivos.
The generous country kitchen connects to several outdoor spaces, while the lower terrace leads to a large brick-lined swimming pool bordered by lavender paths. Everything is designed for leisure, from swimming and pétanque to table tennis and cycling through the surrounding countryside.
La Fornace accommodates up to fourteen guests, which gives it a wonderfully secluded feel. At the same time, it is well suited for larger families or groups of friends. Additional amenities include a private cinema, a library, and a light-filled art studio overlooking the hills. Every corner of the villa is designed to slow down and savor the beauty of Tuscany.
Monteverdi
Monteverdi is located in Castiglioncello del Trinoro, a tiny hilltop settlement with a permanent population of just ten residents. This unusual borgo was revived by Michael Cioffi, who fell in love with the Val d’Orcia. It began as a small bed and breakfast with five rooms and gradually evolved into a full-fledged estate with twenty rooms and three private villas.
Its location is truly remarkable. On one side stretch the velvety hills of the Val d’Orcia and Monte Cetona. On the other, sweeping views open toward Monte Amiata, Montepulciano, and Montalcino, celebrated for their Nobile and Brunello wines. Monteverdi continues to grow and evolve.
In 2023, the osteria-style restaurant Zita opened, serving traditional Tuscan cuisine, alongside a new culinary space, Oreade, a fine-dining restaurant led by chef Riccardo Bacciottini. With just four tables and part of the dining room carved directly into the rock, reservations are essential.
The estate features a bar, a contemporary wellness area with two saunas, a swimming pool, and an outdoor cold plunge, as well as an art gallery showcasing international works curated by London-based curator Sarah McCrory. One of the most memorable experiences is a cooking class with Giancarla, where guests prepare homemade pasta, antipasti, and dessert, followed by dinner under a pergola with views that linger long after the meal ends.
If, after wandering through the Tuscan hills, you feel inspired to continue your wine journey across Italy, explore our guide to wine tours in Italy with hotels and tastings, where locals have selected the best resorts for lovers of Barolo, Brunello, and Prosecco.
