A Tuscan Road Trip

A Tuscan Road Trip

I am driving a Fiat 500, non ironically, down the Via Francigena Pilgrimage Route, an unpaved (under Italian law) dirt road which is flanked by meadows brimming with poppies, lined with Cyprus trees and clad in acres of vines. Corerring down the dirt track, the type that sends Google Maps into a complete tizz and makes you unsure if that is a comfort or an anxiety trigger, you will eventually skid through the gates of a Castello which you can call home for the night.

For my first night, I have arrived at one of these. I will be the first to admit I was raised in a mad house - arguments over spilt milk that make Brexit negotiations look seamless and the odd botched attempted murder. I love my family but I would never go into business with them. The Baccheschi-Berti family think slightly differently. Unfussed by internal politics they have married one another’s strengths to work together and create something straight out of the set of Italy’s answer to Mamma Mia - Castello di Vicarello.

castello di vicarello

A 12th-century castle with epic views over the valley which has one of the most beautiful, though remote, settings in Tuscany. It comes with the atmosphere of a true refuge. The rooms are vast spaces of tranquillity and light, filled with the scent of flowers outside. A labour of love, Neri admits it is a constant tug of war with Aurora his mother (a fashion designer by trade) when it comes to how to furnish each Suite. He looks for a second too long at a mirror on the wall, it is unclear whether that is a battle he once won or lost.

Later, we are seated at a long banquet table in front of a roaring fire and introduced to a chef who looks so excited to feed us I would question his sobriety. The next five courses he produces are so plate lickingly good I forgive him for any substance abuse. Fresh pasta in fresh pesto from the garden, homemade tiramisu, pigeon from the valley and deer tartare which transpires the youngest son shot in their estate forty minutes towards the coast from here.

A couple of glasses of their own award winning organic wine it begins to feel like home. So ensues an Italian hand gesture lesson led by Neri. Determined to learn rude ones we whizz through the basics – ‘what do you mean’ (a finger purse) and ‘I beg you’ (prayer clasp to the chest). In the midst of practising a chin flick motion Carlos father enters. He sees what we are up to and not before flashing a wink to the class he erupts into an Italian tantrum, full of advanced gestures far outside our level of expertise. It transpires we have been learning ‘go f*** yourself’. There is no question that this is the very authentic dolce vita.


Back on the Via Francigena high on a hill in the distance is San Gimignano, where I will have to return another day after spending a little too long ambling in Montepulciano. The hill top towns that define this corner of Italy are plentiful. Just when you think you have got your head round the ‘most famous’ an Italian will announce their go to and so your list grows. It makes getting from one destination to another far less mundane but explains why the drive Google Maps said should take an hour has taken me over two. Slamming on my breaks time and time again to take in a vantage point or roll into a winery to... stretch my legs. Fortunately, I am on Tuscan time where everyday routine rules and regulations are thrown out the window. In Tuscany you can have gelato for breakfast, wine tastings commencing at 10am but if you are looking for a meal between 2.30pm and 5pm, you may find yourself waiting until dinner.

siena cathedral

My next destination is Rosewood Castiglion del Bosco, deep in the Val d’Orcia, a corner of Tuscany that is Tuscany but Tuscany on steroids. Eventually, I career up the sandy road lined with the now customary Cyprus trees to Castiglion del Bosco, a converted 800 year old working wine estate. No longer a working village, the farmhouses now function as luxury villas with views across the region each with expansive personal space inside, outside and poolside. The on site Church boasts original frescos and most of the herbs and vegetables served from the kitchen are grown in the gardens. Staff are courteous, charming and effortlessly bilingual. Even the most extraordinary requests won’t raise the concierges manicured eyebrows.

rosewood catiglion del bosco

There are few things better in this life than experiencing Tuscany the way it should be done — with an abundance of the simplest pleasures: stunning natural scenery to be enjoyed any number of ways fuelled by fresh local produce and watered by some of the best wines in the world. Rosewood Castiglion del Bosco offers just this.

Of course, Tuscany is not all countryside. The regions capital Florence is the birthplace of Renaissance evident in the sheer number of the world’s most valuable artworks that call the city home - almost a third. The cityscape is awash with terracotta and gingerbread rooftops, the prominent Duomo and the brown Arno River, best crossed at the Ponte Vecchio. The city’s squares are fit for fairy tales and even if you tried to avoid them, there is a centuries old church around every turn. Although the tourist traps are inevitable in this well explored city there are still a cluster of trattorias filled more with local mammas than braying Brits. The Oltrarno District on the south side of the river feels more local and Santa Maria Novella retains a sense of peace and calm perhaps aided by the scent of the perfumery next door where monks still produce the famous cologne. When it comes to places to rest your head after days exploring there is a wealth of choice both in the thick of it or in the foothills of Fiesole. With more luxury options than Rome, there really is something for everyone. Really.


It is little wonder why Tuscany has been the backdrop of so many movies, books, plays, and novels. The cobblestone streets, endless green hills dotted with poppies, and the daily choice of fresh pizza or homemade pasta washed down with gelato make for an idyllic escape or expedition.

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