best escapes in the Tuscan Countryside this autumn

2 November 2022
Written by Lucrezia Worthington

During Autumn, Tuscany is one of the most extraordinary landscapes to visit due to the mesmerising hues of nature and the endless experiences that this season allows. Truffle hunting to wine tasting as well al fresco aperitifs at sunset (if the climate allows) are the bases of an unforgettable stay in this region, not to mention the exquisite, rich and varied cuisine. We have gathered 10 hotels to explore this season in the region of Tuscany from the Chianti hills to the Maremma countryside,


Il Borro,

Il Borro, Relais & Châteaux, is a historical location whose origins date back to the early 20th century. Acquired by the Ferragamo family in 1993, the estate has been restored whilst preserving its ancient, medieval beauty. The Rooms & suites, spread out among the hamlet, are beautifully furnished with country chic furnishings and artisan textiles. Wine, art and sustainability are the core principals at Il Borro; aspects that naturally intertwine from biodynamically farming their wine to the interests of Ferruccio Ferragamo in exposing the origins of wine (and the role of women with wine) through his art collection that can be viewed during a wine tasting experience. Il Borro features 3 swimming pools, a gym, a spa and a medieval village with artisans working their crafts as well as two culinary offers: Il Borro Tuscan Bistrot, an informal concept with a tuscan based menu and The Osteria del Borro, a gourmet restaurant focused on delivering farm to table cuisine with fresh and seasonal ingredients that come from the Estate and locally sourced produce from small local artisans. During the day you can organise various activities that span from horse riding to picnics by the vineyards, visits to the local artisan workshops and cooking classes: everything to bring you closer to an authentic Tuscany. WEBSITE

Tuscany hotel
Deluxe Suite at Il Borro. Ph. Francesca Pagliai


Villa San Michele, firenze

Twenty minutes away from Florence, Villa San Michele, a Belmond Hotel, is a renaissance masterpiece carved into the Fiesole hilltops (where Leonardo da Vinci first attempted to fly). An ex monastery that dates back to the sixteenth century which today has been converted into a sensational hotel that preserves its heritage through architecture, artworks and the exceptional facade designed by the school of Michelangelo. La Loggia is the beating heart of the hotel, a restaurant with a view who’s menu has been curated by Executive Chef Alessandro Cozzolino. The cuisine is focused on traditional and local recipes combined with a creative, contemporary flair. From picnics in the garden to poolside lunches, walks around the flower lined gardens and mesmerising sunsets Villa San Michele provides the ultimate setting for an authentic tuscan experience. WEBSITE

La Loggia Restaurant, Villa San Michele. Ph. Mattia Aquila


Il Salviatino,

Il Salviatino is situated in Fiesole, on the outskirts of Florence, and is housed inside a sumptuous Renaissance country villa. The concept of the hotel is to preserve the heritage of the past with a contemporary vision. The design is pristine, with period furnishings and prestigious marble materials that feature in the rooms & suites. Although minimally designed, every element has been selected with precision and you’ll find a blend of both artisanal works with the latest technologies. Step out onto the porch from where you’ll witness a splendid view over the skyline of the city (and the swimming pool). Here you can enjoy your morning breakfast as well as lunch, an aperitif and dinner. The restaurant is in the hands of Giacomo, a group of restaurants founded in Milan back in 1958 by a Tuscan pioneer and since then, has been serving exquisite cuisine that touches upon the tuscan roots with Milanese classics. WEBSITE

Tuscany Hotels
Il Salviatino


Castel monastero, siena

Castel Monastero is a medieval oasis nestled among the hills of the Chianti Classico region, less than 30 minutes away from Siena. It’s an ex monastery surrounded by millennia old walls that today has been converted into a 74 room + 1 villa hotel. Each space has been designed to emphasise the heritage of the monastery with a rustic, chic outlook. A central piazzetta is enclosed between the rooms, offering a relaxed environment for morning breakfast or an aperitif. There is ‘La Cantina’, a wine cellar and restaurant that dates back to the XIII century to when the nuns used to produce olive oil. Here and at ‘Contrada’, guests can enjoy a fine dining experience. Wellness plays an important role in this enchanting space that houses a SPA with jacuzzi, hammam, two saunas, sensorial showers, gym and an extensive massage and treatment menu. WEBSITE

Castel Monastero


Borgo San Felice,

Borgo San Felice is a place where time is immediately erased. The borgo, or medieval village, dates back to the Etruscan area and became a noble residence in the eighteenth century. Explore the hamlet, walking by cypress trees and foliage as the birds chirp away from morning to evening and witness some of the most breathtaking sunrises and sunsets from your room window (or vineyards). One of the core pillars at Borgo San Felice is the preservation of Nature through various elements, whether it’s the harvesting of indigenous grapes (ask to taste the Pugnitello wine) or the use of seasonal and homegrown produce from the vegetable garden in the cuisine. Poggio Rosso is the Michelin starred restaurant led by Executive Chef Juan Quintero, a young and extremely talented chef who is the youngest international Chef in Italy to have achieved a star. His cuisine is an expression of the territory, tied in with Latin American elements. A ‘must’ taste is the risotto with Chianti rice, wild bore and cypress tree – the epitome of Tuscany in an unusual dish that uses the essence of cypress tree to balance out the stronger tasting wild bore. All to be enjoyed in the elegant space to the sound of live pianoforte and crackling fire during the colder season. WEBSITE

Borgo San Felice


Villa La Massa,

On the riverside along the banks of the Arno, Villa La Massa stands proudly with its Renaissance splendour that dates back to the 13th century. What used to be a country house for the Medici family is now a proud member of the Leading Hotels of the World and part of Villa D’Este hotels since 1998. Surrounded by cypress trees and olive groves, Villa La Massa provides the ultimate setting for a tranquil escape, whilst being conveniently located a mere fifteen minutes from the centre of Florence (you can take advantage of the free shuttle bus that takes you to and from the city centre almost every hour). The design is noble, classical, with period furnishings from the antiques to embroidered fabrics. Enjoy an aperitivo at The Medicean Bar with its 19th century frescoes and signature cocktails prepared with exclusive liqueurs by Officina Profumo-Farmaceutica di Santa Marina Novella before heading to ‘Il Verrocchio’ for dinner signed by Chef Stefano Ballarino who curates a cuisine that combines tuscan classics (yes, a 1kg Florentine Steak is guaranteed on the menu) with only seasonal produce, in fact the menu changes every two months. WEBSITE

Il Verrocchio restaurant overlooking the Arno river


Castello di Casole, siena

Castello di Casole, a Belmond hotel, is an enchanting 10th century estate surrounded by a 4,200 acres of rolling hills, sweeping valleys, vineyards and olive groves. Easy to reach, the hotel is located 67 km away from Florence, yet offers a complete immersion into the countryside. A refuge for those seeking to experience rural Tuscany in contemporary styled rooms that look out into the wild, untouched nature. Spend the day visiting local farms, spotting wildlife or hunting for truffles during the autumn season and retreat to the estate at sundown as you sip an aperitif with a mesmerising view. Then take a seat at Ristorante Tosca to savour authentic Tuscan flavours in which simple recipes are executed with the freshest, local ingredients by Chef Daniele Sera. Before you head back to your rooms don’t forget to gaze up at the stars on a clear night sky and see how many stars and planets you can spot! WEBSITE

Bedroom at Castello di Casole


Como Castello del Nero,

COMO Castello del Nero is a historic estate, located in the Chianti area. As the name suggests, the heart of this prestigious resort is a 12th century manor house, with 50 rooms and suites, surrounded by an estate of about 300 hectares with vineyards, olive groves and numerous beehives. All the rooms and suites are spacious and neatly designed but differ in size and shape as they depend on the architectural features of the building. There are three restaurants in COMO Castello Del Nero. La Torre, one Michelin star, in winter is located in the premises that formerly housed the stables, while in summer it moves to the garden terrace. All menus are supervised by executive chef Giovanni Luca di Pirro who has an approach rooted in the local culinary tradition. The second, informal restaurant is called La Taverna and is housed in the ancient kitchens of the castle, dating back to the 12th century. Informal atmosphere also in the third restaurant, The Pavillon, open only in summer like La Taverna and overlooking the hills, which offers dishes inspired by the Mediterranean. For moments of sport and relaxation on the property there are tennis courts, a heated outdoor pool and the COMO Shambhala Retreat spa, where guests are pampered with the expertise for which the COMO Shambhala brand is known: a 360-degree approach to wellness which aims to improve the physical, mental and spiritual well-being of each with a comprehensive range of treatments. WEBSITE

Terrace bedroom at COMO Castello del Nero


argiano dimore,

Immersed in the natural setting of the grand 16th century Villa Bell’Aria, the ‘Dimore’ are the estate’s annexes, designed in a rustic chic style and surrounded by 300 acres of olive groves and vineyards. Sienese architect Filippo Scheggi was in charge of the design, which he lovingly carried out through repurposing and upcycling old and unused materials converting them into libraries, tables and lampshades. Spread across five old stone farmhouses, the rooms, suites and apartments are decorated in natural hues and available to be rented as a whole (also featuring a kitchen) or as separate. Each farmhouse features a private garden and access to a swimming pool. On the culinary front, head down to Sala Ara Jani, a finely restored old barrel cellar in which the Chef prepares a 4 course tasting menu based around seasonal produce. Renowned for its production of wine, the Estate was also one of the founding companies of the Brunello di Montalcino Consortium in 1967. This deep bond with the territory is now celebrated with a collection of the most iconic bottles of Brunello (as well as Supertuscan Solengo and Rosso di Montalcino), preserved along the walls of a vertical cellar, obtained in the cistern of an ancient well. Private tours and tastings are available to book upon request during your stay. WEBSITE

Tuscany hotel
One of the apartments at Argiano Dimore


Castello di Vicarello, grosseto

Powerful and solitary, it was built by the Sienese around 1200 as a defense and sighting outpost to control the valleys below. From its ancient terraces, the eye still today sweeps towards infinite horizons, over intact and absolute panoramas. Owned by Carlo and Aurora Baccheschi Berti, it is divided into various structures harmoniously arranged and connected, surrounded by a well-kept garden. An exclusive stay for a few, suitable for romantic getaways or refined weekends with friends, it offers hospitality in 7 rooms with antique furnishings that combine with oriental-style elements. The decoration is that of a private house where the taste for details, books, knick-knacks tell a story of a couple, of life, of family. WEBSITE

Where to sleep in Tuscany
Bathroom in the suite of Castello di Vicarello

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