Chianti, Café Culture and Cookery Classes: an Authentic Tuscan Experience 

I’m standing in the centre of a cobblestoned medieval square that looks as though it’s caving in, and wondering if it’s taken this shape over time. Perhaps the Palio di Siena (referred to as one of the most lawless horse races on earth) has something to do with it?

Piazza del Campo is the square in question and my host, English historian, Kitty, quickly dismisses the theory surrounding the Unesco World Heritage Site. The thronging marketplace was constructed as a central water drain for this city built on a hill; the annual race that’s taken place here for centuries between the city’s historic contrade (districts) is not to blame.

It turns out the Sienese are quite big on preservation; in the early 1960s Siena became the first Italian city to impose driving restrictions within its historic walls, in order to curb traffic and retain its rustic charm. With a population of around 50,000 people, and deluges of tourists each year on day trips from Florence to see Renaissance works by Michelangelo and Donatello at the Duomo, the small city quickly becomes congested.

Many draw artistic and cultural parallels between Siena and the Tuscan capital, Florence, an hour’s drive away. And while you can get a feel for the medieval city and the surrounding hills of the Chianti region in an afternoon, the authentic local experience demands a little more of your time.

Kitty’s good friend Alessandra Aloe is behind one of the world’s best thrifting spots, Aloe & Wolf. International press clocked her thoughtful curation of 20th-century European men and womenswear which includes brands such as Yves Saint Laurent, Chloé and CP Company. With mates’ rates thrown in, three unique items made their way into my suitcase.

Before thumbing through the rails we made like the Italians with a pit stop for espresso at a popular local joint, Il Bargello. Kitty tipped us off that necking it at the bar lets you swerve the service charge if you’re after a quick caffeine hit – a well-known native hack. That’s not to say you shouldn’t sit and enjoy a pastry too if you’ve got a bit more time on your hands.

In the Piazza del Campo, numerous cafés jostle for attention and provide caffeine hits for those considering climbing to the top of Torre del Mangia. There are only 400 steps between you and the peak of one of the tallest secular towers in Italy. It offers a great vantage point of the city if you’ve got the stamina (and haven’t spent too long shopping beforehand).

Unfortunately we didn’t make it to the Duomo – too many tourists on day trips concentrated here – though we did visit another important Sienese landmark. Santa Maria della Scala, now a museum, was one of the first hospitals in Europe, and frescos on its well-preserved walls tell stories of those who found solace here; pilgrims en route to Rome, abandoned children and the infirm were all taken care of within its walls. The interiors haven’t changed since the 15th century – and it feels ominously relevant in light of the coronavirus pandemic.

For more than a decade Torre Palazzone, an Etruscan-era castle, has been in Kitty’s family. Less than 15km (9mi) from Siena, you can book to stay here via Tuscany Now and More which boasts an impressive portfolio of more than 130 luxury Italian villa rentals. Madonna reportedly stayed in the Palazzone’s fantastical Duomo Suite, a 1,000-year-old chapel that’s the oldest and arguably most spectacular part of the castle. Kitty thought I’d appreciate its gothic vibes, so I settled into the plush king-size bed and tried not to feel spooked; with its starry ceiling inspired by Santa Maria della Scala, it feels more arty than eerie.

The Duomo Suite is one of 11 rooms in the castle, which advertises itself as a wedding venue or secluded getaway for groups of up to 22 people. It’s not surprising that celebrities come here on holiday; with its winding drive, quintessentially Tuscan rolling hills and vineyards, and outlines of neighbouring castles like Villa Cetinale (built by Pope Alexander VII in the 17th century), the castle is a stunning escape. The small village of Sovicille, a short drive away, offers rustic eateries and further charm.

To give you some idea of its size, it’s thought that Torre Palazzone once played host to an entire community. The remote spot is well signposted, and you’ll be greeted by a heated swimming pool, wood-fired pizza oven and loggia that doubles up as a dining or studio space in its ample grounds.

It was a little too chilly to swim when I was visiting late in the year, so I opted to stay warm by the outdoor pizza oven while getting to know the resident chef, Georgia. Tuscany Now and More is able to organise all sorts of experiences for guests including tours of Siena with Kitty, marbling classes in the barn with her partner, James, and cookery classes with Georgia. Panzanella, pappa al pomodoro and tiramisu were a few of the delicious local dishes I mastered under her watchful eye.

Tuscany is renowned for its wine, and five minutes on foot from the palazzone is a 9ha (22-acre) vineyard with vermentino, cabernet sauvignon and merlot grape varieties. From the castle bedrooms you get a brilliant view over the Tenuta di Trecciano estate; book a tour of the grounds to walk among the vines and learn all about the winemaking process. When it comes to sampling some of the best exports, oenophiles will be hard-pressed to find fault in its 2012 Chianti Riserva vintage.

To soak up the few-too-many wines from the tasting, book in at a lesser-known local eatery. Il Ristoro di Ponte allo Spino is an unassuming family-run spot en route to Siena through the Montagnola Senese region. This trattoria whips up the very best pici cacio e pepe – a cheesy pasta with plenty of black pepper; it’s a true Tuscan classic and a must-try dish. Indeed, there are many must-tries in Tuscany – I hope to return and continue working my way through the list.