The Val d’Orcia in Tuscany is about as iconic a landscape as exists. The endless vistas of cultivated fields, sinuous rows of cypresses inscribed across them, medieval towns and churches clinging fast to the summits of gentle hills – they elicit an aha! surge of recognition, even among those who have never set foot in the area. In May it is as green as Ireland, the grass undulating in the warm late-spring wind like acres of emerald silk. By July the hills are burnished gold, pollen in the air casting the late-afternoon sun in an iridescent haze. And by August’s end, the fields are all fallow, sere earth, hardened under a blazing-white sky – the curiously bleached, almost lunar vista of late summer for which this area has become particularly famous.
But come November, the Val d’Orcia undergoes an identity shift. After October rains have softened the sun-baked fields back into dark sable soil and the last of the mid-autumn winds have roared up the ramparts of the medieval walled cities, a still, hushed, entirely sui generis sort of magic arrives in this pocket of southern Tuscany. The hills are bedazzled with hoarfrost, bowls of dense mist slowly rolling between them; the crisp air carries the bitter, alluring aroma of burning olive wood and the peals of bells from cathedrals miles away. The streets of the surrounding towns – the same ones that in July are sometimes almost impassable for all the wine, cheese and vista-hungry masses – are, if you get them at the right moment of the day, as near-deserted as they might have been 25, or 200, years ago. The traditions of this season are calibrated to shorter days, richer foods, bracing temperatures. The festivals are more obscure, and so perhaps more enchanting. All the famous signifiers – those cypresses, those farmhouses – are still present and accounted for, but the context has totally changed.
Eventually, some clever person was going to deduce that travellers might like a deep-dive into the sleeping side of such a destination – not just in the Val d’Orcia, but any area of quintessential summertime appeal: Sicily, or the Luberon, or the spiffy, WASP-y shores of New England. And it so happens that a few enterprising hospitality minds have this year elected to keep their resorts, villas and inns that are normally closed from November to March open through the winter months. And by curating some compelling attractions – foods and festivities, cultural events and nature immersions –that are unique to the period, they hope to shift their off season into the spotlight.
Massimo Ferragamo is among them. The New York-based chairman of his family’s US operations is also the owner of Rosewood Castiglion del Bosco, a 5,000-acre, 800-year-old Val d’Orcia estate located to the northwest of Montalcino, which he has spent around 11 years painstakingly restoring as a resort and golf club, much of it housed in the beautifully reimagined ruins of the 12th-century borgo and a handful of 17th- and 18th-century farmhouses. Ferragamo’s vision for Castiglion del Bosco is one of immaculate luxury of the sort more commonly associated with Italy’s five-star urban hotels than its rural, wooded reaches. But due respect for the humble vernacular of the local architecture (about which, in the event, there is no choice here in the Val d’Orcia, made a Unesco World Heritage Site in 2004 and one of the most rigorously protected regions in the country) coupled with the interior ministrations of his talented wife Chiara have resulted in a place of unassailable elegance – plausibly rustic on the outside, harbouring state-of-the-art creature comforts within. Two years ago Ferragamo brought in Rosewood Hotels & Resorts to oversee the operations of the hotel, whose suites are spread throughout the villa padronale and outbuildings of the original borgo. Like the other country resorts around here, it closes from November to April; but the estate’s 11 villas – ranging from three to six bedrooms, and set amid its numerous vineyards, overlooking the private golf course, or secluded amid cypresses next to the ruins of a medieval tower – will, for the first time this year, remain open to guests through the winter. “The first time I visited Val d’Orcia was in the winter; I was totally captured by it,” says Ferragamo. “The off-season months are infused with peace and quietude. The colours of the woods, that typical morning mist hiding the rising sun; it adds great romanticism to what I think of as a still-untouched part of Tuscany.”
To underscore his belief, Ferragamo’s ground team has created a series of private and semi-private experiences for villa guests. November is olio nuovo season, when the olives are milled and cold-pressed for premium oils; tours and tastings of them have become something of a thing among gourmands, much as whisky tastings have among spirits enthusiasts. The finest mills in the area will open their doors for Castiglion del Bosco villa guests to take part in the olive harvest and they can also visit the annual, and very local, festa dell’olio in the charming (and still quite unspoilt) town of San Quirico in the company of a local oil producer. Late November and December are peak truffle season; Castiglion del Bosco will arrange on-foot hunts accompanied by dogs, and a guided visit to the white truffle festival in San Giovanni d’Asso – along with, it perhaps goes without saying, a truffle tasting at the truffle hunter guide’s own farmhouse. For those looking for something more bracing, there’s horse riding at local stables; and the ancient hot springs at Bagno Vignoni, some 40 minutes’ drive to the south – used by the Etruscans and Romans, and (unbeknown to many) open all year. And in February – the deepest sleep of winter here, when dustings of snow adorn the summit of Monte Amiata like baker’s sugar on a sweet – the wineries release their vintages. The finest Brunello di Montalcino, Vino Nobile di Montepulciano and boutique DOC red blends are made public for the first time; guests at Castiglion del Bosco have the opportunity to be among the very first to sample them in the annual hosted tastings. (Though the estate’s own winery – with its staggeringly cool private wine club, housed in a subterranean vault, and multi-award-winning Brunellos – may prove hard to outdo. Normally during the winter months it’s open only to its international roster of members, but villa guests have access.)
Some 480 miles away, deep in the forests of Ménerbes in Provence, the hotelier-tastemaker par excellence Jocelyne Sibuet has struck a similar idea. La Bastide de Marie, the 14-room boutique hotel that she opened in 2000, will for the second year running open throughout Christmas and New Year, allowing guests – many of whom are longtime Sibuet supporters and repeat bookers – to immerse in a Luberon that’s light years away aesthetically and experientially from the languid, cicada-chorus days of high summer. “Winter here is magical,” she says. “It’s authentic and generous in a totally different way to summer. The colours are outstanding, for one thing, but it is the festive traditions that mark this period out as unique.” As in Tuscany, it is also prime truffle season; for her guests, Sibuet, like the team at Castiglion del Bosco, has enlisted a cohort of seasoned local truffle hunters, with chefs on deck back at the inn to magic the spoils of their efforts into rib-sticking suppers, one of which will culminate in the preparation and serving of the traditional 13 Christmas Provençal desserts, featuring figs, almonds, black and white nougat, quince paste, dried and candied fruits, and – unexpectedly but deliciously – sweet focaccia. She has also parlayed her own local expertise in the rich Christmas market traditions, parades and nativity scenes into immersive guest experiences, and will dispatch them with a series of chefs and guides to the best of these, including the famous antiques market at L’Isle-sur-la-Sorgue and Avignon’s lit-by-a-thousand-candles spectacle.
The summer siren call of Sicily’s baroque east coast is a famously powerful one, from the Greek-Roman amphitheatre and sorbet-coloured charms of Taormina to the white-stone lanes of ancient Ortigia and wide beaches of the Vendicari nature reserve. What fewer people know is that some of the island’s loveliest moments unfold in the depths of winter. In December and January the acres of citrus trees between Mount Etna and the Ionian Sea are heavy with vibrant orange and yellow fruit; the skies are van Ruisdael masterpieces of fast-mutating cloud, as rains give way to surprisingly temperate sunshine. And Sicilian Christmas traditions, as any student of culture and culinary history knows, faithfully (and deliciously) reflect the island’s palimpsest history of Greek, Arab and European dominion. Huw and Rossella Beaugié, the team behind The Thinking Traveller, the portfolio of top-flight catered villas, farmhouses and palaces across the island, have for some years now actively marketed a small selection of their best properties during December and January, with local chefs, family recipes, tastings of boutique Etna wines, concerts and festivals. This year the list expands to 28; and the season-specific accoutrements and services range from traditional nativity scenes and Christmas trees assembled in-villa, to private choral and concert performances and Opera dei Pupi, the traditional holiday puppet theatre. At the 12-bedroom, 12-bathroom Don Arcangelo all’Olmo, set on a bluff overlooking the sea just north of Catania, holiday-season guests can enjoy all of the above, along with a Christmas menu developed by the aristocratic owners’ old monzù – the chefs who specialised in the fine French-inspired cuisine (the term is a corruption of monsieur) typical of the Neapolitan and Sicilian aristocratic households of the 18th and 19th centuries – whose pièce de résistance is a turkey brined and braised in local Marsala wine, with vegetables in agrumi [citrus fruit].
Across the Atlantic, in the quintessential New England summer destination of Rhode Island, the holiday shutters tend to come down just after Labor Day weekend, that ceremonious American close to the summer season. Certainly, post-Thanksgiving, few holidaymakers are along the coast. Now, though, one of the state’s most distinguished hotels is dispensing with convention to stay open throughout the year. The 67-room Ocean House – which opened in 1868 – has already earned some serious kudos since reopening in 2010 under new ownership after a two-year, $145m facelift. Now it’s launching winter-centric programmes – many of which, in keeping with that mix of hearty outdoorsmanship and cosy indoor living that’s typical of Rhode Island high-WASP culture, involve getting close to nature. Birding and seal-spotting, for instance, both unique to winter here: migratory seabirds, including threatened duck species, briefly colonise the low-lying coastal wetlands around the hotel in December to forage on their way south. Ocean House naturalists guide excursions to watch them in action, or take guests out on its sister hotel’s vintage skiff to scout for the endemic harbour seals that return to the warmer waters of the lagoon around the same time, to wait out the frigid months.
Back at the hotel there will be gingerbread and wassail in lieu of lobster rolls, and warm knitted throws next to fires instead of sipping Southsides in the Adirondack chairs out on the deck. The familiar coordinates of summer, seen from the perspective of winter: as in picture-perfect Italy and the south of France, it’s bound to be an exhilarating switch-up, and not just because it’s cold outside.