Italy: Why autumn is the best time to visit

Rome: Italy is a place that lives up to the hype. An inarguably stunning destination, the country plays hosts to nearly 100 million tourists every year, but herein lies a problem: Italy—especially well-known hotspots like Tuscany and the Amalfi Coast—can very easily lose some of their allure under the crush of too many tourists.

However, just because a path is well-beaten doesn’t mean it should never be taken. By the time the fresh, amber-tinged air of autumn arrives in the shoulder season (October and November), crowds lessen all across Italy, and there is a shift that extends beyond just the weather. Fewer tourists, it turns out, is only one of many charms Italy offers in the autumn season.

In Tuscany, fall is harvest season. Though many tourists come to these legendary cypress-lined hills for the wine, few ever witness grapes being picked; wineries humming in earnest; or vineyards growing as russet-red as the last sip of Sangiovese. The wind picks up this time of year. Olives plump, blacken, fall. Mushrooms sprout overnight. Dishes grow hotter and heartier, and the earth ripens and reddens.

At one of Tuscany’s top boutique hotels, Castello di Vicarello, which operates under the adoring ownership of the Baccheschi Berti family for whom it was once a family home, the mood changes too—especially in the kitchen.

Surrounded by 40 hectors of farmland, Castello di Vicarello is still very much a living, breathing estate with its own exquisite wine; peppery, punchy olive oil; and organic vegetable gardens. Thus, autumn remains a busy time despite the dwindling numbers of visitors checking into the nine-key property on Tuscany’s untamed Maremma coast, but that doesn’t mean there isn’t plenty for guests to do. “There are some experiences that you can do all year round like our cooking classes and wine tastings,” says Neri Baccheschi Berti, CEO of Castello di Vicarello, “but truffle hunting, mushroom hunting, olive harvest, grape harvest—you can only do this part of the year.”

Traditional Tuscan cuisine shines during the season, with truffle-topped pappardelle; dense chestnut flour castagnaccio cakes; and hearty vegetables soups like acquacotta (“It’s not one specific recipe, it’s what’s seasonal in the vegetable garden,” says Baccheschi Berti). At Castello di Vicarello, Head Chef Kevin Luigi Fomoni makes the most of the property’s in-season offering of dark cavolo nero, fragrant fennel, fresh eggs (collected from the Castello’s own hens); and an almost endless supply of mushrooms. “It’s the season of the porcini,” says Baccheschi Berti, “in one day mushroom hunting you can come back with ten-plus kilos.”

It’s not just the food that changes with the season in Tuscany. Daily life goes from al fresco to al forno, and evenings are spent in front of the hearth. “We still have some days where you can lie by the pool and soak up some sun, but you’re also able to have a nice glass of wine in front of the fireplace, which is a particular experience,” says Baccheschi Berti.

It’s a particular experience indeed: From the outside, Castello di Vicarello is postcard-perfect Tuscany, a cluster of centuries-old stone edifices nesting on a particularly spectacular slice of country hillside, but it is only when you spend time indoors that you grasp what makes the property truly special. Fitted with corners that are as much cozy as they are contemporary and dressed in plush furniture; cool light features; and one-off antiques handpicked from Bali (where the family once had a home), Castello di Vicarello is equally impressive on the inside as it is from the outside. “It’s the mix of Italian and Indonesian design that gives the particular vibe to this place,” says Baccheschi Berti, who had a hand in the gorgeous modern-classic interiors. “When you want to define the soul of a property by just it’s geographical location, I think it’s superficial. This is fresh. This isn’t a place to be, as the Italians would say, puzza sotto il naso [snobbish]. People can relax, they can let go…Here there is no room you cannot enter.”

Six hours south of the Castello in the tourist-haven of the Amalfi Coast, life also changes in the autumn; but here, it is not so much about the harvest or the switch to cozy indoor living. Instead, it’s a chance to see the Costiera Amalfitana like a local and appreciate the small, seasonal delights that many visitors miss.

“When I see the cyclamen, I know winter is coming,” says sixth-generation lemon farmer Salvatore Aceto, plucking at the little purple flowers that dots the terraces of his Sfusato Amalfitano lemons. Though the lemon harvest is long finished come autumn, zesty clementines are now in season and dangle heavy from the trees like Christmas baubles. Also, the sour-sweet verdelli lemons can now be picked for limoncello with a distinctive greenish tinge, proving every season has its spoils.

Having the coast to yourself is a particular joy. Most tourists will never know what it’s like to spool down spaghetti-skinny corniche roads without the clog of tour buses or stroll quaint alleyways without the constant drone of English.

Even in October, temperatures are still mild and the sea is warm enough to enjoy. Also, as the tourist season officially lasts until the beginning of November, many hotels remain open until then, and to visit without the normal demands of full occupancy is a delight.

There is no better time to check-in to the five-star Monastero Santa Rosa Hotel & Spa, a former seventeenth-century Dominican monastery balanced atop a magnificent Conca dei Marini cliff just outside of the town of Amalfi. Cliché as it may be, it’s easy to rely on words like “divine” and “heavenly” when talking about Monastero Santa Rosa. With understated but high-end amenities and even a functioning church, Monastero Santa Rosa could inspire even the most fervent of atheists to thank the heavens for a single night on these hallowed grounds.

The hotel—one of the best in all of Italy—is exceptional at any time of the year, but it’s the kind of place that’s even more so when it’s serene, harking back to former days, when only nuns roamed its cloistered halls. With some of the best views in all of Italy, the 20-key property takes on a rarified air at the end of the season, when few other guests can disturb the sublime peace.

White-washed rooms are named after flowers cultivated in the terraced gardens. Hand towels are refreshed with rosewater. Echoing hallways of Jerusalem stone, flaming candles and vaulted ceiling are scented with basins of dried aromatic herbs. Robes are fluffy as freshly whisked zabaglione. Santa Maria Novella toiletries and pomegranate bath salts make cocoons out of marbled bathrooms. “Divine” and “heavenly” may, in fact, be understatements, especially when considering the pool. Seemingly suspended just below heaven, Monastero Santa Rosa’s lapis blue infinity pool is the stuff of which Instagram dreams are made. The best part? It’s heated, meaning it can be enjoyed right up until November.

The hotel’s subterranean spa is another treat at this time, with bubbling hot tubs; experience showers; and steam rooms, billowing thyme-scented white mist—all almost completely empty. At breakfast on the terrace under late-flowering vines and reddening climbing ivy, late-season guests are doted upon with impossibly flakey shell-shaped sfogliatella (once made by the nuns) and thick-creamed cappuccinos, served in goblet-sized mugs offering up cheerful bongiornos in sky-blue script.

The food at Monastero Santa Rosa—from the crunchy dried Calabrian peppers served with the cocktails to the Michelin-starred coastal cuisine of Il Refettorio—will be the highlight of any trip. Chef Christoph Bob is an expert in Southern Italian simplicity-meets-generosity: Warm cakes ooze Amalfi citrus like Vesuvius; crisped vegetables come plucked right from the nuns’ gardens; and the catch of the day is seared to flakey, moist perfection over local lava stones. Meals conclude with a benediction of homemade herby, minted amaro. All the ingredients are clearly chosen with purpose, and locality plays as much of a role as seasonality in Chef Bob’s kitchens.

At this time of the year, the 62-strong staff have all the time in the world for you, and they are quick with recommendations and warm conversation. (Though surely, the service is always this flawless, no matter the time of the year.)

Both the Amalfi Coast and Tuscany can now be enjoyed together via the Italy Driving Experience, a new self-driving itinerary that combines the two family-owned boutique hotels, Castello di Vicarello and Monastero Santa Rosa Hotel & Spa. A vintage Alfa Romeo Dutteo is provided for the duration of the six-night trip, and costs start from €8,040. Contact Monastero Santa Rosa Hotel & Spa and Castello di Vicarello to book.