Travel Diary - Tuscany on the Road

FrancescaBenettiGenolini
May 13, 2019
4 min read

A white uphill road, a cypress tree to mark the way.

After the turn, an abandoned farmhouse behind a Romanesque tower.

All around, only for coves and hills, and a cypress tree to mark the way.

Tuscany is this, Tuscany is much more than our eyes are used to.

Bolgheri

With its iconic cypress tree boulevard, that romantically accompanies drivers to the town castle, this little gem is one a favourite destination for wine lovers, attracted by prestigious Sassicaia, but also curious tourist, inevitably fascinated by the lovely borgo and its small shops, churches and restaurants overlooking the hills.

It won’t take long to understand why Giosue’ Carducci, Nobel prize italian poet, has been so much influenced by these landscapes, and dedicated some of its most beautiful compositions to the land that nourished him (it’s worth reading Davanti San Guido before visiting Bolgheri).

Volterra

Perched on one of the many hills of Tuscany, and protected by the IVth century fortification walls, Volterra is a real Medieval treasure. Although many millennials might be disappointed to find out that Twilight’s Saga was not actually shot here, the town is famous for the impressive Palazzo dei Priori (oldest town hall in Tuscany), the XIIIth century Cathedral and the Roman theatre that dates back to Ist century BC.

Cobbled streets and medieval buildings create a magical background for artisan workshops, famous for the production of Alabastro, typical osterie where you can taste local cheeses and a timeless atmosphere that doesn’t seem to be affected by the passing of time.

Siena

No praise would be exhaustive enough to describe the beauty, richness and dramatic atmosphere of Florence’s eternal enemy, a history that captures your heart, and leaves you speechless every time.

Possibly the most romantic and breathtaking city in Tuscany, Siena is a one surprising open-air museum; from its marvelous contrade (districts) that still preserve that colourful folk of the XVIIth century, when the famous Palio was inaugurated, to the incredible Libreria Piccolomini and gothic Duomo (with the suggestive staircase that reveals the façade only at last) and, of course, the unique Piazza del Campo, the XIIth century sloping square that host every year the world-famous horse race and attracts locals and tourists with its iconic view of the Torre del Mangia.

Val D’Orcia

Miles away from the dense vegetation and endless vineyards of Chianti, starts the most picturesque area of the region, Val D’Orcia. Characterised by isolated cypress trees, hilltop hamlets and curvy roads this poetic landscape, where nothing seems to be left to the case, whispers to the astonished viewer history and tradition, between medieval castles, rural farmhouses and endless beauty.

Bagno Vignoni

Located in the very heart of Val D’Orcia, this Roman village is absolutely unique in his kind. With its main square’s “thermal pool”, the sixteenth-century spa that was attended by Popes and nobles of the time, medieval cobbled streets and pretty shops, this hamlet is the perfect pit-stop to enjoy a stylish lunch or wine tasting before hitting the road again.

Until June 2019 the main square hosts a beautiful installation by artist Davide dell’Osso called “the magic garden”, make sure you check it out it if you happen to visit!

Pienza

Another unmissable gem of Val D’orcia, and UNESCO heritage site since 1996, Pienza owes its name to Pope Pius II Piccolomini, who was born here and later commissioned entire village to be rebuilt following the ideal Renaissance town, and offers probably the most terrific views over the valley.

Take your time to visit the beautiful Duomo, explore Palazzo Piccolomini and walk around the marvelous alleys, stop for a taste of their famous Pecorino cheese and indulge in typical meal at Osteria Sette di Vino, a tiny, genuine restaurant where Luciano will make you feel at home with his mouth watering dishes of the Tuscan tradition.

Chianti

Enchanted vineyards, quaint hamlets and fine wines, all framed by soft hills and warm sunsets. This is Chianti Classico, the oldest and most genuine area of Chianti region, and driving around these curvy roads is like getting lost in countless dreams, from spectacular vineyards to castled villages that still reveal Tuscany’s pristine beauty.

If you decide to spend the night around you can treat yourself at beautiful Borgo di Pietrafitta Relais, a romantic property that offers the most relaxing experiences, from daytime excursions at the discovery of Chianti to delicious tastings in their own cellar, always ending with a bespoke aperitivo by the pool at sunset or a panoramic barbecue.

Our favourite vineyard was Castello di Ama where, for almost 20 years, the winery’s owners have invited artists, from Anish Kapoor to Daniel Buren, to collaborate to a unique open air museum that can be explored through fascinating guided tours and tastings.

San Gimignano

To be completely honest, I found myself the most astonished when seeing this walled town from the valley, dominating with its fourteen towers like medieval skyscrapers...

As you enter the original gate, everything is beautifully intact, almost perfect, but it pays its beauty at high price; touristy shops and street vendors populate the cobbled streets, selling slices of pizza to hungry visitors and typical souvenirs to school caravans…

Fortunately, the main route is soon interrupted by a series of picturesque alleys and marvellous squares, hidden churches and panoramic views that would make you forgive even the biggest crowd. Visit the Romanesque Cathedral Collegiata, or the unusual - but extraordinary - modern art collection at Galleria Continua and the Palazzo Comunale, fuel up with a real tuscan meal at La Vecchia Nicchia and climb one of the towers for a spectacular view.

Pisa

Although many only associate Pisa with its leaning tower, one of the most famous engineering mistakes in history, this city is actually a real gem in his kind, with many more noteworthy sights and secrets to discover. Home to one of the oldest and most prestigious universities in the world, the city centre is characterised by a vibrant street life, set in a beautiful frame of Romanesque buildings, Gothic churches and Renaissance piazzas.

Head to Piazza delle Vettovaglie and Lungarno for young local nightlife and, while wandering around tiny alleys and riverfront, don’t miss architectural gems such as Santa Maria della Spina, Scuola Normale and, of course, Piazza dei Miracoli.