“Let’s just stick a pin in a map and go there.” It’s a romantic idea, isn’t it? But have any of us really followed it through? Whenever I try it, I usually hit an ocean or a desert or a slum. Fail!
Well, there is a place that, wherever the pin lands, you’re guaranteed incredible food, charming locals and postcard photos. Ladies and gentlemen, I give you TUSCANY!
Here’s the best advice I can give anyone visiting this incredible region of Italy: base yourself in a town, hire a car and do day trips out to the different villages and castellos. We stayed in Siena, a central city in Tuscany, and it proved to be an excellent choice.
Don’t try to do too much. If you’re in Tuscany for a week, don’t expect to be able to explore Florence, Siena, Lucca and Pisa as well as go to all the little Etruscan hilltop towns that make Tuscany so beautiful.
Florence is a holiday on its own. It’ll still be there the next time you visit… and believe me, you will be back!
Here’s what we did in our week in Tuscany:
Allowing some time to explore Siena itself (more on that to come), we spent four days exploring the winding roads and hilltop towns of Tuscany.
Day 1: Cortona
Cortona’s about a 180km round trip to this steep hilltop town on the Umbrian border – and it’s well worth the drive. It’s an ancient town with an Etruscan heritage. It was also used in the making of the movie Under the Tuscan Sun.
Walk up to the top of the town to the little church with some amazing frescos and even more amazing restoration work going on there.
The main piazza – Piazza Garibaldi – is quite small but lovely, and ideal for people-watching over a beer or a coffee.
This little town is very pretty and good for a quick leg-stretch and a gelato. It was also where our friends Nick and Kerry got married!
As you drive back to Siena, keep an eye out for any little towns peeping out of the hills on the horizon. We found so many little places that were all different and all breath-taking.
Day 2: San Gimignano (pronounced ‘jim-in-yano’) and Certaldo – about 120km round trip
These two sister cities are spectacular. Peering at each other from neighbouring hilltops, they overlook the pastoral lowlands of Tuscany.
San Gimignano – also known as ‘the town of 100 towers’ or ‘the city of beautiful towers’ – is an incredible place. Only a handful of the city’s towers still remain, but the ones that do are impressive.
The tallest, Torre Grosso built in 1311, stands at 54 metres. They loom like huge brick monoliths and form, as UNESCO describe it, “an unforgettable skyline”.
Certaldo – from the walls of this elevated medieval town you can see the towers of San Gimignano some 10km away.
Certaldo’s a picturesque little town, full of the shops, trattorias and osterias that you expect to find. Getting into the town is great too.
There’s a cable car that takes you up into Certaldo Alto, which is the old town part, so no need to exhaust yourself! The cable car goes from the main piazza-cum-car park and takes you through a timewarp.
Day 3: Volterra – about 35km from Siena
It’s hardly surprising the set-hunters for the Twilight franchise chose to base parts of their vamp-mance movies in Volterra. The place refuses to let you forget you’re walking within the walls of an ancient place full of history and rich in tales.
Volterra is an incredible place and well worth spending at least half a day just wandering around its narrow cobbled streets. Once inside its walls, you’re immediately struck by its uniqueness. The higher you go in the town, the more unusual it gets.
We went higher and higher until we found a great park and botanic gardens. Then, right at the top, an enormous walled building. Turns out it’s a high security prison. If you’re hungry, you can even have dinner there – cooked by none other than its residents! Make sure you book though, it’s remarkably popular!
Day 4: the beach – about 140km round trip
From Siena, head south-west to Grosseto. The marina there is lovely and so is the beach. Quite different from a lot of the narrow beaches surrounding the Mediterranean, this one is deep and roomy! However, the ubiquitous rows of sun loungers are here too – the cost of privately managed beaches.
We were lucky enough to find an exquisite salumeria and feasted on a platter of beautiful wild boar prosciutto – a Tuscan specialty, ham, salami, fresh bread and of course delicious cheese.
Castiglione della Pescaia
A little further up the coast is Castiglione della Pescaia. This seaside town is so beautiful you’ll want to pull your eyes out and leave them there so you’ll be able to look at the place forever!
Head up hill to find the old castello, now only inhabited by the fluttering, dive-bombing swifts. The outlook from its walls is mesmerizing.
The rest of our seven days of heaven were spent exploring our base town of Siena and heading back to Pisa and its busy little airport.
While in Pisa, you have to stop in at the Torre pendente di Pisa – or the Leaning Tower of Pisa. It’s a bit of a tourist circus but it you should see it.
We didn’t just get these places from a guidebook or guesswork. A dear family friend is from Tuscany. He knows the region so well, he says he could “travel around Tuscany with my eyes closed and still know exactly where I am.”
What a waste that would be, Riccardo – going around Tuscany with your eyes closed? Madness!