“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.
Lucignano
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!
Kimberley
How am I meant to concentrate on work now. All I want to do is plan a trip to Tuscany. Beautiful pictures.
Mrs Romance
Thanks Kimberley! It’s suh an easy place to photograph. Makes me want to go back there now too x
Heidi
What beautiful pictures!!! Tuscany has been my #1 destination since I was in high school!
Mr Romance
Hi Heidi, it’s a fantastic holiday destination. We wish we were back there now!
Riccardo
TO MY DEAREST MR AND MRS ROMANCE
Thank you for mentioning my assistance. I am thrilled you loved Tuscany as much as I do.
As to going around blind folded, I tell you what……………next time I’ll come too and I’ll take bets
Cheers
Mr Romance
Hi Riccardo
You’re on! Thanks again for making our trip so memorable with all of your help and advice. And thanks for commenting on our site!
see you soon
Jim
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Arvind
A wonderful and punchy review of your travels in Tuscany! Thank you.
I’m planning a 10-ish day vacay with my wife for this September. Where did you guys stay? Thanks 🙂
Mr Romance
Thank you, Arvind! We had a great time in Tuscany. I hope you and your family have a great time too.
We staying in Hotel Alex in Sienna and based ourselves there. It’s well-located so we drove around the countryside from there. It was perfect.
Cheers
Jim
Margaret
Hi Jim, we will be in Florence in April for a week and i am trying to find someone that does small group tours hopefully to Cortona and Arezzo, can you recommend anyone? we don’t want to pay the price for a private tour. We drove last time we were there from Florence to Udine and swore we would never drive again…….i nearly had a nervous breakdown….but we survived!
Mr Romance
Hi Margaret. We only did self-drive trips to towns through Tuscany. We just parked up as close as we could on the outskirts of town and walked in. It mitigated the risk of crashing, not being able to find a parking spot and not running someone over! We did see a few walking tours in the Tuscan towns we visited but other than the one we did in Orvieto in Umbria, we didn’t do any tours.
Sorry we couldn’t be more helpful – you might be able to find more info when you’re in each town though. They usually have pretty good tourist information offices that can help. Have an amazing trip though. Sounds like you’ll be in Italy for a while. I’m very jealous!
Jxx
vinaina
Hi Jim, loved your blog. Beautiful pictures! My husband and I are planning a trip to italy in Sept this year, and will be in Siena for 3 nights. We are thinking of doing two day trips (starting from Siena):
Day 1 – Pienza, Montepulciano, Montalcino
Day 2- San Gimignano and Chanti
Does this sound doable to you? Since we are not very familiar with the region, will self driving be a good option?
Mr Romance
Hi Vinaina. So glad you like our blog. Your trip to Italy sounds great. Quite jealous actually! Yes, your itinerary for the two days sounds very doable. Siena is a great hub to explore Tuscany – though make sure you do look round Siena itself while you’re there. Beautiful town.
Driving in Italy – especially in Tuscany – is a lot of fun. I’d definitely recommend it. You get so much more freedom when you have your own transport. Just make sure you get GPS. Saved us a few times.
Also we’d recommend not making any plans too hard or too fast. When you’re driving around Italy, expect to be distracted by a little town or village, a pretty lake or old castello on your way. To get the best out of Tuscany, you have to embrace the diversion. It’s an enchanting place. If you like proscuitto, make sure you have some Tuscan proscuitto – it’s the local delicacy, is made with wild boar and is sweeter than others. It’s so good!
Have an amazing trip.
Buon viaggio!
Jim
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