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Diaries of a Tuscan Sun

October 20, 2019

 – Tuscany Guide 

Part 2/2

The winding roads and the green and yellow tapestries of Tuscan. Now that  is a sight.

For those of you that follow me on instagram, you probably know that one of the main reasons for my incursion into Tuscany was to host a photography and storytelling workshop there, alongside with Veronica Charlott — something that I will dive into as soon as I am able to. So, between that and a few days after, I had the chance to visit a little bit of Tuscany. Unfortunately, it was not as extensive as I would have liked. But, to be honest, I was much in need of a good R&R and ended up visiting just a handful of places that Tuscany has to offer. Nonetheless, I did a thorough research on the region; that, together with some inside information from some friends and family that have lived or stayed there, meant that I could (without any reservations) put up a guide for you, if you ever think about discovering the region.

Now, the first thing you need to know, is that Tuscany is huge. It is a region divided into sub-regions with Florence as it’s capital — so you can get an idea of how vast it is. To get around you will need a car, because public transportation can be quite scarce. And the second thing you need to know is that it is as beautiful as everyone says. 

Everywhere we looked, there was a hilltop with a borgo (common name for a small settlement outside the walls of an ancient town), a sepia building with a tower-like building and a view surrounding it that until this day has me speechless.

Tuscany has such a unique artistic legacy, being it the birth of the Italian Renaissance, that if you are anything like me — a history geek — you will understand and marvel at the contours in which one of the best periods in art was born. The colours of the land, the views of it, and the fact that it had a political proclivity for the arts (think Medici, one of the most renowned patron of the arts and it’s constant war with the Vatican to elect the best of the best artists), I think it was inevitable that something like the Renaissance was predestined to happen.

We headed south to the outskirts of Pienza. At the Val d’Orcia we had one of the most breathtaking tours of the region, with it’s little towns overlooking that vast paradise punctuated with rolls of haystack and the lone cypress trees delimiting the dusty roads all the way to the tawny arches that celebrated the entrance of an ancient town, medieval castles or simple farmhouses, each one telling a story of it’s own. Pienza, between Montepulciano and Montalcino (also worth a visit), is a mandatory stop if you ever encounter yourself on that bailiwick, and not only for the Pecorino cheese and the pici pasta — a thick pasta rolled by hand, typical from the Tuscan region — but also for the simple fact that it is beautiful, overlooking the vale, with it’s own little duomo, palazzos, cathedral and quintessential shops that you could spend half a day lost in.

Up north, towards Arezzo, stop by Cortona and venture to the chianti wine region all the way to Sienna. Here, the golden wheat fields are replaced by the green slopes of endless vineyards, to an extent that it feels like you are in a whole different country, were it not for the aged farmhouses overlooking the land and the brick constructions peaking in from the ridges. 

We stayed at Le Fontanelle, a XIV century farm turned into a beautiful Hotel, with unparalleled views of that region and a just a short car ride from Sienna. At our Tuscan address, we could venture in the botanic and herbs garden where the chef still goes to pick up some of the essentials for dinner, or relax by the pool or spa, admire the corners of the gardens or marvel at the vineyards at our feet and taste the sweet grapes used to produce the chianti wines. It was the perfect dwelling for our stay in Tuscany. 

Although, confessedly all I really wanted to do was to enjoy the perks of our new abode, Sienna was something I really did not want to miss. And the road leading to that quaint Comune was nothing other than beautiful. Now, Sienna is undoubtedly crowded, and understandably so. The shell-shaped medieval Piazza del Campo, where everyone gathers, and back in the day, where it all lead, is surmounted by the City Hall with its leading tower rising on one end. It is like a giant amphitheater made to delight any visitor. Irradiating from it, charming narrow streets thread the way to the beautiful fabric of Sienna, that it is like walking back in time. Cheese shops, Leather goods, Trattorias and Osterias, all unravels efforthlessly between the Palazzos and numerous arches that can be found here and there. My advice? Explore without a destination. I think it is what most villages like that are made for.

I picked up dinner from a secretive cheese and wine shop, bought some focaccia, cold cuts, an olive cheeseboard and truffle jar with something of a patê in it and called it a win. Alongside with the chianti wine gently provided by the Hotel and some local grapes, it felt that life could not be any more wonderful as it was. 

It was hard to realise that all of that inevitably had to come to an end. But before going back home, we managed to make a last stop at Valdirose, to have a look at the insta-famous B&B or — as I call it — a photographers haven. The place is as beautiful as it is advertised, Paolo and Irene have an amazing eye for detail and the kindest disposition to make anyone feel at home. From the mouthwatering breakfast to the lavender scented pillows, everything is made to make your stay eventful.

Now, in retrospective of my time in Tuscany, all I have to say is that it is that kind of place one must come back to every now and then in life. There is so much to do and see, and although nothing will radically change (because, in a way, that is its motto), it is a place to inspire, wonder, discover and rediscover every time.

I did have fun, more than I could ever anticipate, a promise easily kept on that night in September back in Lisbon, before my heart got lost in the hills of Toscana.


  • Pienza
  • Montepulciano
  • Volterra
  • San Gimignano
  • Cortona
  • Sienna
  • Arezzo
  • Val D’Orcia
  • Chianti Wine Region


  • Hotel Le Fontanelle, Pianella
  • Trattoria La Buca delle Fate, Pienza
  • La Taverna di San Giuseppe, Sienna
  • Grotta Santa Caterina da Bagoga, Sienna
  • Pasta Demonstration and Lunch at Il Rigo, Val d’Orcia
  • Il Faconiere, Cortona


  • Hotel le Fontanelle, near Sienna
  • Relais Borgo Santo Pietro, near Monticiano
  • Il Rigo, Val d’Orcia
  • Valdirose, near Florence
  • Conti di San Bonifacio, near Gavorrano
  • Relais Sant’Elena, near Bibona


  • Fairs and Gastronomic markets (see calendar here)
  • Cheese, specially Pecorino
  • Chianti Wine
  • Cold Cuts
  • Antiques
  • Olive wooden goods

Notes: Tuscany is filled with terrible mosquito strains this time of the year. A strong spray and cream are strongly advised.

Thank you Inês, Tina and Paola for coming along in this adventure.

Thank you also Hotel Le Fontanelle and Maaris for sponsoring this post.

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