How to spend a week in Tuscany, Italy

“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!

Mr and Mrs Romance Italy Tuscany Siena Florence Pisa Cortona Lucignano San Gimignano Certaldo Volterra Grosseto Castiglione della Pascaia

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!

Mr and Mrs Romance Italy Tuscany Siena Florence Pisa Cortona Lucignano San Gimignano Certaldo Volterra Grosseto Castiglione della Pascaia

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

Mr and Mrs Romance Italy Tuscany Siena Florence Pisa Cortona Lucignano San Gimignano Certaldo Volterra Grosseto Castiglione della Pascaia

Mr and Mrs Romance Italy Tuscany Siena Florence Pisa Cortona Lucignano San Gimignano Certaldo Volterra Grosseto Castiglione della Pascaia

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

Mr and Mrs Romance Italy Tuscany Siena Florence Pisa Cortona Lucignano San Gimignano Certaldo Volterra Grosseto Castiglione della Pascaia

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.

Mr and Mrs Romance Italy Tuscany Siena Florence Pisa Cortona Lucignano San Gimignano Certaldo Volterra Grosseto Castiglione della Pascaia

Mr and Mrs Romance Italy Tuscany Siena Florence Pisa Cortona Lucignano San Gimignano Certaldo Volterra Grosseto Castiglione della Pascaia

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”.

Mr and Mrs Romance Italy Tuscany Siena Florence Pisa Cortona Lucignano San Gimignano Certaldo Volterra Grosseto Castiglione della Pascaia

Certaldo – from the walls of this elevated medieval town you can see the towers of San Gimignano some 10km away.

Mr and Mrs Romance Italy Tuscany Siena Florence Pisa Cortona Lucignano San Gimignano Certaldo Volterra Grosseto Castiglione della Pascaia

Mr and Mrs Romance Italy Tuscany Siena Florence Pisa Cortona Lucignano San Gimignano Certaldo Volterra Grosseto Castiglione della Pascaia

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.

Mr and Mrs Romance Italy Tuscany Siena Florence Pisa Cortona Lucignano San Gimignano Certaldo Volterra Grosseto Castiglione della Pascaia

Day 3: Volterra – about 35km from Siena

Mr and Mrs Romance Italy Tuscany Siena Florence Pisa Cortona Lucignano San Gimignano Certaldo Volterra Grosseto Castiglione della Pascaia

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.

Mr and Mrs Romance Italy Tuscany Siena Florence Pisa Cortona Lucignano San Gimignano Certaldo Volterra Grosseto Castiglione della Pascaia

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

Mr and Mrs Romance Italy Tuscany Siena Florence Pisa Cortona Lucignano San Gimignano Certaldo Volterra Grosseto Castiglione della Pascaia

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.

Mr and Mrs Romance Italy Tuscany Siena Florence Pisa Cortona Lucignano San Gimignano Certaldo Volterra Grosseto Castiglione della Pascaia

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

Mr and Mrs Romance Italy Tuscany Siena Florence Pisa Cortona Lucignano San Gimignano Certaldo Volterra Grosseto Castiglione della Pascaia

Mr and Mrs Romance Italy Tuscany Siena Florence Pisa Cortona Lucignano San Gimignano Certaldo Volterra Grosseto Castiglione della Pascaia

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.

Mr and Mrs Romance Italy Tuscany Siena Florence Pisa Cortona Lucignano San Gimignano Certaldo Volterra Grosseto Castiglione della Pascaia

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.

Mr and Mrs Romance Italy Tuscany Siena Florence Pisa Cortona Lucignano San Gimignano Certaldo Volterra Grosseto Castiglione della Pascaia

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!

Images by Mrs Romance.

16 Comments

  • Reply April 22, 2013

    Kimberley

    How am I meant to concentrate on work now. All I want to do is plan a trip to Tuscany. Beautiful pictures.

    • Reply April 22, 2013

      Mrs Romance

      Thanks Kimberley! It’s suh an easy place to photograph. Makes me want to go back there now too x

  • Reply April 24, 2013

    Heidi

    What beautiful pictures!!! Tuscany has been my #1 destination since I was in high school!

    • Reply April 24, 2013

      Mr Romance

      Hi Heidi, it’s a fantastic holiday destination. We wish we were back there now!

  • Reply April 25, 2013

    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

    • Reply April 25, 2013

      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

  • […] we head north on our way to Paris by way of Dijon. We stop by Avignon for a quick break. Ever since we stayed in Siena last year, (and Tallin before that) we have a thing for walled cities. Avignon is spectacular. This is the […]

  • […] we head north on our way to Paris by way of Dijon. We stop by Avignon for a quick break. Ever since we stayed in Siena last year, (and Tallin before that) we have a thing for walled cities. Avignon is spectacular. This is the […]

  • […] We’re driving through an industrial estate somewhere in Tuscany and our GPS doesn’t even know where we’re going, sending us down a dirt lane way. We’ve been driving a fair bit through the Tuscan countryside already by this point, so we’re not put off by the unsealed road. Here’s our post on how to spend a week in Tuscany. […]

  • […] Of all the Tuscan cities to use as a base, I do believe Siena is the best. It’s big enough to keep you entertained on days you don’t feel like heading out in the car to explore the rest of Tuscany. […]

  • Reply July 3, 2014

    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 🙂

    • Reply July 3, 2014

      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

  • Reply January 12, 2015

    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!

    • Reply January 15, 2015

      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

  • Reply June 15, 2015

    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?

    • Reply June 15, 2015

      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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