Not Your Typical Tuscany Trip

Not Your Typical Tuscany Trip

There is a reason Tuscany evokes such vivid imagery and is a dream destination for many people. I bet even as you read the title of this blog, you had a picture in your mind of rolling hills and pointy cyprus pine trees running along long driveways leading up to sun bleached, slightly crumbling villas and ancient villages perched on top of the rolling hills. It’s one of the most recognisable landscapes in the world and justifiably so. It really is that gorgeous and it really does look like the photos and movies. Perhaps more beautiful in real life actually, because it’s difficult to capture the quality of the light in Tuscany and do it justice.

I’ve been to Florence many times and would happily return to that sophisticated city again and again and Sienna is just a magical place. They should both be on any Tuscan itinerary. But on this trip, I was very keen to get out into the hills and villages of Tuscany. I wanted a mix of the revered, famous towns and hopefully discover some little gems I hadn’t heard of (not an easy ask in one of the most well known holiday destinations in the world). I passed through Tuscany twice on this trip. Once with Mum on our way through to the wine festival in Marino and once alone on my way back up north. I’ve put together some of my highlights that perhaps will encourage you to get a car (you can find some tips for driving in Europe here) and go exploring around this beautiful province and find some of the lesser known spots, as well as the classics.

Cortona

I really didn’t know much about Cortona at all, Mum and I just happened to be staying in an Airbnb nearby! Turns out that it is the town where the movie was filmed that started a lot of women of a certain age’s Tuscan dreaming, ‘Under the Tuscan Sun’ with Dianne Lane. It is a typical Tuscan town, set high on a hill, surrounded by walls and fortresses. We visited in early October, when the weather was still warm, but the first hint of autumn was apparent in the cool breeze and the tourist crowds were dissipating. The largely car free centre of town was utterly charming. Wide streets, lined with sophisticated leather shops and galleries and restaurants. There were two large piazzas where locals and tourists alike gathered at tables to drink an aperitivo or sit on a bench and watch the world go by. It immediately felt like somewhere you should get an apartment for a month and just blend into the life there. I get it Diane Lane, I get it.

  • Grab a gelato at Gelateria Snoopy on Piazza Luca Signorelli and eat it sitting on the steps of the Town Hall.
  • If you are in town on a Thursday from May to October, Molesini wine enoteca holds free wine tastings every afternoon from 3-6pm. They also have a dinner following the tasting, reservations necessary.
  • La Locanda del Molino is a restaurant and small hotel about 15 minutes drive from Cortona. The appetizer board is enormous – be prepared to go light on mains! The wines are exclusively from their own vineyard and that’s totally fine as they are delicious. They also run cooking classes, would love to try one out some day!

Marina di Alberese 

I had never associated Tuscany with the beach. But my Airbnb host recommended Marina di Alberese and it was going to be a beautiful sunny day in October, so I figured why not? The beach is located in a National Park and there are a limited number of vehicles allowed in at any one time. Apparently huge queues form in summer but this was not an issue in October. Me and a few other groups of people (primarily German tourists) had the whole beach to ourselves. There were shade shelters constructed out of drift wood all along the grey, sandy beach which made for an interesting walk, as did the lack of clothing the further along the beach you went! No sun lounges and umbrellas and waiters on this beach – so unusual for Italy! The park goes right up to the beach (a curious fox spent some time checking us all out) and the water was clear and calm and still fairly warm. If you need to cool off for a day during your Tuscan adventures or just want to see something a bit different, this is a great option.

Montalcino

Poggio Antico

Montalcino is the home of Brunello wine. Along with Barolo from Piedmont, this is one of Italy’s most famous and revered wines. It was the first to receive DOGC status in Italy in 1980. Brunello must be made out of 100% sangiovese grapes and must come from a designated region made up of only 3000 acres of vines. There are many other rules to determine if a wine can be named Brunello as set out by the Denominazione di Origine Controllata (more to come on that system soon).

I wanted to try a few Tuscan wines and decided to visit a couple of wineries. Poggio Antico, whilst still a family business and only a medium sized producer, was a slick operation. It’s set on 500 acres of gorgeous land (not all planted with vines, just the worthy soil), high on a hill with stunning views over the Tuscan hills. It’s worth heading out there for the view alone. Tony gave our small tour group a comprehensive tour in English of the cellars, informing us about the wine classification system in Italy, the types of wines made in Tuscany, the wine making process and about Poggio Antico’s wines and history. A tasting followed with a variety of options depending on how much you wanted to spend and taste! If you’d like to learn about their wines in a bit more detail, this is a great article from the Wine Geeks.

Osteria di Porta

Poggio Antico also has a fine dining restaurant on site, but I wanted to have a look around the town of Montalcino so decided to have lunch in the town. I initially arrived alone at Osteria di Porta, just near the fortress, and there was a ten minute wait for a table. They sent me outside to the little park across the road with a glass of Brunello – that was just fine with me! When my table was ready, I walked into the restaurant to find a group of ladies from Colorado who had been on the tour at Poggio Antico. The friendly waiter happily set me a place with them and my table for one was quickly snapped up. We ate Tuscan classics; hearty ribollita soup (a mix of beans, vegetables and bread so thick it’s almost a stew), hand rolled pinci pasta with wild boar ragu, rabbit, cheese and salumi. We talked about our travels, drank great wine, laughed and generally had a very Tuscan lunch experience indeed! Loads of fun.

San Gimignano – Sovestro in Poggio

San Gimignano is one of those famous Tuscan towns you just have to see at some stage. I only had a quick look around as I was en route to Modena that day. I wanted to combine a visit here with one more winery, preferably a very small one and found Sovestro in Poggio online. They were easy to book a tour with over email. They are a true agritourism business (Italy does this very well), offering accommodation, cooking classes, wine tastings and lunch in addition to being a fully functional vineyard. I did a tour, learning more about Tuscan wines, the classification process and their own wines and then joined the others on the tour for lunch on a lovely terrace, overlooking the vineyards. This consisted of traditional Tuscan soup, ribollita (quite a different version to Osteria di Porta) and a cheese and meat platter, along with some of the wines from the vineyard. At €35 for the tour, tastings and lunch, it was fantastic value for money. I would have happily ordered another bottle of wine and settled in for the afternoon if I didn’t have a drive ahead of me.

Tuscany is one of those places I am likely to return to. Apparently there’s a great walk between Florence and Rome… Do you have any recommendations for off the beaten track spots? Would love to hear them!