Tuscany at Harvest: Private Villas, Borghi and the Long Autumn Table

Tuscany is at its most generous when the land is working. The vendemmia, the grape harvest, runs through September and into October; the olives follow from late October into November, when the new oil is pressed green and peppery; and autumn brings truffles to the woods and fires to the long tables. Spring, from late April to June, is the other great season, all long light and quiet roads. The short answer to where to stay is a house of your own on a working estate, and the harvest weeks are the first to go.

We keep Tuscany deliberately short: three houses we know well, a restored hamlet near Volterra, an owner-kept villa among the Chianti vines and a hillside of villas above the sea, with Florence within reach of each.

Borgo Pignano: a hamlet near Volterra, nine villas wide

Borgo Pignano is a borgo in the truest sense: a hamlet first settled in Etruscan times and documented since 1139, set some 500 metres up at the heart of a 750-acre organic estate and restored stone by stone with local materials. Woods, orchards, olive groves, lakes and an organic vineyard fall away toward the Berignone and Castelvecchio nature reserves, and scattered through them are nine private villas, each with its own pool and garden. The hamlet itself keeps two older houses: La Canonica, the medieval priest’s house beside the Church of San Bartolomeo, and La Casa del Guardia, in a seventeenth-century stone building.

Each villa has its own character. The Artists’ House sits in an oak and beech copse with a studio and a wood-burning stove; Il Poggiarello stands alone on a hill facing Volterra; Casa del Lago looks over a pond ringed with poplars. For families, Il Poggio has a heated infinity pool and a wood-fired oven, La Fonte, beside one of the lakes, sleeps up to eleven, and Villa Cusignano holds six bedrooms in about 1,000 square metres, with breakfast cooked by a private chef.

At harvest the estate comes into its own. At Villa Pignano, chef Angelantonio Cioffi’s cooking holds a Michelin Green Star, and in spring and autumn Il Camino gathers guests at one long table beside an open fire for the estate’s hand-cured ham and bistecca alla fiorentina. The cellar pours Borgo Pignano’s own organic wines, and the olive oil and Millefiori honey come from the same land. Mornings might go to a truffle hunt with a Lagotto Romagnolo, or to the herbalist’s workshop; afternoons to La Cisterna Spa in the medieval well-house, or the Cave Pool, cut from an old limestone quarry.

Volterra and the hill towns

Fifteen kilometres away, Volterra rises nearly 1,800 feet above the valleys of the Era and the Cecina: an Etruscan town with its Piazza dei Priori, its Medici fortress, its alabaster workshops, and an Etruscan Museum that rewards a morning. A complimentary shuttle runs from the estate each day. Further out, Lajatico’s Teatro del Silenzio, Lucca, Pisa and the cypress avenue into Bolgheri’s wine country each make a comfortable day, and Florence is a little over an hour by road. Bolgheri is the country of Sassicaia, Ornellaia and Masseto, and a cellar visit there is best arranged as the harvest ends and the winemakers have time to talk.

This is the quiet pleasure of the borghi, the walled hamlets that grew around a castle, a church or a crossroads: each keeps its own hours, its own feast days and its own table, and the best of them are still lived in. A week here moves between them at walking pace.

Villa Gran Sogno: five rooms among the Chianti vines

Between Florence and Siena, just outside Castellina in Chianti, Villa Gran Sogno keeps a smaller scale: an adults-only house of five king rooms under timber beams and old stone, with a private pool and vineyards and olive groves on every side. Connie and Mauro, the owners, are in residence through the season. At harvest the days fill themselves: a private Chianti wine tour, an olive oil tasting, a market morning that ends with cooking and lunch at the villa, and the cellars of Radda, Panzano and Greve a short drive along the hill roads.

Argentario Golf Villas: Tuscany with the sea in it

At Tuscany’s southern edge, Monte Argentario was once an island; now the Orbetello lagoon, where flamingos wade, lies between the promontory and the Maremma. In a green valley between its two harbour towns, Porto Ercole and Porto Santo Stefano, Argentario Golf Villas sit on the hillside of a car-free, 77-hectare estate of cork oak and centuries-old olive trees where fallow deer still roam, above Italy’s only PGA National golf course.

There are three kinds of house, each with an annex: a three-bedroom Maremma Cottage for six, a four-bedroom cottage for eight, and the six-bedroom Hills Lodge for twelve, with interiors by Andrea Fogli and teak terraces that look over the course to the lagoon. Breakfast is at the resort or cooked by a private chef on your terrace, and dinner is at Dama Dama, where chef Emiliano Lombardelli, born on the Argentario, cooks from the resort’s organic garden and the farms of the Maremma.

Days turn on golf, the sea and the Maremma: a skippered boat to the promontory’s coves, a ferry to Giglio or Giannutri, a ride with the butteri toward the Uccellina park, the warm waters of Saturnia. Late October brings the Gustatus food and wine festival to Orbetello, and the mild climate keeps the course in play all year. Villa guests use the 2,700-square-metre Espace Wellness Center every day, its heated saline pool running from indoors to out and open through the winter. Rome Fiumicino is about an hour and a half by road.

The harvest calendar

• September. The vendemmia begins across the Tuscan hills. Villa Pignano serves lunch and dinner every day, and the sunset ride from Borgo Pignano’s stables to Prosecco Rock runs until the end of the month.
• October. The later grapes, the first truffles, and the fire lit at Il Camino; a quiet hour in Montalcino before the tasting rooms fill; on the coast, Gustatus in Orbetello at the end of the month.
• November. The olive harvest and the new oil. Many countryside estates shorten their calendar from late autumn, so dates are confirmed with the house; the Argentario stays open, with golf and a heated indoor pool.
• Spring and summer. Late April to June for long light and quiet roads; July and August for Al Fresco’s outdoor grill at Borgo Pignano and the beach club on the Giannella shore.

Florence, and a week between city and country

Florence is the city we pair with each of these houses: about 65 kilometres from Borgo Pignano, and a natural first stop before the drive south to the coast. Our Florence & Tuscany journey holds eight nights as one stay, four in the city with museums by appointment and four among the vines, with a driver who already knows which gate opens. Autumn suits the city too. The crowds of summer thin, the galleries are calmer, and in November the trattorie greet the new oil the old way, poured green over grilled bread and salted: the fettunta is the simplest taste of the Tuscan year and among the best.

Choosing your Tuscany

• For a borgo of your own: Villa Cusignano or La Fonte at Borgo Pignano.
• For two: The Artists’ House, or Il Poggiarello alone on its hill.
• For the harvest table: Borgo Pignano in September and October.
• For an adults-only house in Chianti: Villa Gran Sogno, by the room or taken whole for up to ten.
• For sea, golf and the Maremma: the Hills Lodge at Argentario Golf Villas.
• For city and country together: the Florence & Tuscany journey.

Begin the conversation

A Tuscan week begins with a few details: who is travelling, the season, and whether the days should end at a long table in the hills or on a terrace above the sea. Share them through Plan My Trip, and a dedicated advisor will match the villa to the party and settle the dates with the estate, privately and by hand.