Tuscany in Autumn: A Luxury Weekend Among the Vineyards
Five addresses across Chianti, Val d'Orcia and Valdarno, and the looks to wear there
There is a moment in the year when Tuscany seems to slow down. The hills turn from green to gold, the wineries fill with the scent of new wine and the olive mills prepare the season's oil. This is autumn, and for a luxury weekend in Tuscany it may be the most beautiful time of all.
Once summer ends, the villages grow quiet again, the light softens and the days invite a different rhythm: a walk through the vines, a lunch that lasts all afternoon, a dinner by the fireplace.
Style changes with the season too. Warm materials like cashmere, suede and nappa come in, along with the colours of earth and wine and enveloping silhouettes. Every choice complements the place without ever overpowering it, just like an Alevì Milano shoe: Italian elegance built on craftsmanship and attention to detail.
We have chosen five addresses, each for a different kind of weekend.
Rosewood Castiglion del Bosco, Montalcino
The Brunello weekend
In the heart of the Val d'Orcia, a UNESCO World Heritage Site, Castiglion del Bosco is a medieval village restored and transformed into a luxury estate. Its vineyards are devoted entirely to Sangiovese, the grape behind Brunello di Montalcino.
Here, autumn is lived in the cellar: tastings, walks through the vines and dinner at the Michelin-starred Campo del Drago, overlooking the hills. The spa is set in the estate's former wine cellar.
The look? A tall cashmere boot, a trench coat and a soft sweater: practical elegance, ready for the vineyard.
Rosewood Castiglion del Bosco, Montalcino
COMO Castello del Nero, Chianti
The romantic castle weekend
Between Florence and Siena, in Barberino Tavarnelle, stands a 12th-century castle surrounded by 300 hectares of vineyards and olive groves. Frescoes, beamed ceilings and contemporary interiors sit together effortlessly.
It is the ideal address for a getaway for two: an afternoon treatment at the COMO Shambhala spa, followed by dinner at La Torre, awarded one Michelin star.
For the evening: a dark silk dress, gold jewellery and an Alevì Milano jewelled slingback.
COMO Castello del Nero, Chianti
Borgo San Felice, Chianti Classico
The village weekend
Twenty minutes from Siena, Borgo San Felice is an entire medieval village turned into a scattered hotel and a member of Relais & Châteaux. Stone lanes, small piazzas and the original cellars tell the story of the most authentic Tuscany.
In autumn you can set out on a truffle hunt across the estate, guided by an expert and his dog, and end the day at the Michelin-starred Poggio Rosso.
The mood is pure village life: knitwear, straight-leg trousers and a nappa ankle boot in wine tones.
Borgo San Felice, Chianti Classico
Il Borro, Valdarno
The art and craftsmanship weekend
Between Florence and Arezzo, Il Borro is a medieval village at the heart of an organic estate of more than one thousand hectares, owned by the Ferragamo family since 1993. Beyond its suites, wine and spa, the village is home to the workshops of artisans at work: a tribute to Tuscan craftsmanship.
It is the perfect place for anyone who loves to discover how beautiful things are made, between a winery visit and dinner at the Osteria del Borro.
An essential, polished look: a blazer, a silk scarf and a suede pump.
Il Borro, Valdarno
Tuscany, a Way of Living Autumn
In Tuscany, autumn is not a season in between.
It is the moment when the land gives back what it has kept: wine, oil, colour. And style follows the same rhythm, made of materials that warm, deep tones and carefully chosen details.
Because luxury here is above all about time: for a lunch in no hurry, a walk at sunset, a dinner that lingers by the fire.
Tuscany Style Guide by Alevì Milano
Friday evening, the arrival
Cashmere Sweater |
Stuoia Midi Skirt |
Silver and Gold Choker Necklace |
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Saturday morning, among the vines
Cotton Shirt |
Trench Coat |
Wool Trousers |
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FAQ
When is the best time for an autumn weekend in Tuscany?
October and November are ideal. In October the harvest comes to an end and the landscape reaches its richest colours; in November the new olive oil season begins. The summer crowds are gone, temperatures are mild and many resorts offer seasonal experiences such as wine tastings and truffle hunts.
Where to stay in Tuscany for a luxury weekend?
Among the most exclusive addresses are Rosewood Castiglion del Bosco in Montalcino, COMO Castello del Nero and Borgo San Felice in Chianti, Fonteverde in San Casciano dei Bagni and Il Borro in Valdarno. Each offers a different experience: wine, a castle, a village, thermal baths or craftsmanship.
Chianti or Val d'Orcia for an autumn weekend?
Chianti, between Florence and Siena, is ideal for villages, castles and wineries within a short drive of each other. The Val d'Orcia, further south, offers wider landscapes, Brunello di Montalcino and thermal baths. For a first weekend, Chianti is more convenient; for a more contemplative experience, choose the Val d'Orcia.
What to wear to an autumn wine tasting?
Layers work best: a trench or light coat, a cashmere sweater and comfortable trousers. Cellars are cool and visits often include time outdoors among the vines. Neutral or earthy colours such as camel, chocolate and bordeaux are both elegant and practical.
Which shoes to pack for an autumn weekend in Tuscany?
You need at least two pairs: a boot or loafer for walks through vineyards and villages, where gravel and stone are common, and a more precious shoe for dinner, such as a mule or a jewelled slingback. A mid-heel ankle boot works from lunch through to evening.
Images: Pinterest.