Postcards from Tuscany


I always describe Tuscany as my ‘happy place’. We’ve visited so many times now that as soon as we head off from Pisa airport in the car I can feel myself start to breathe in more deeply, and becoming more relaxed. I’m not sure if it’s the green of the vineyards, the good food, the amazing wine, the nice weather, or the friendly people, or just the way they all come together to create one of the most magical places on earth.

Of course, I’m slightly biased, as Tuscany is where my husband proposed, and where we honeymooned, so there is a huge amount of nostalgia for us there too. Which is one of the reasons why we were so keen to take Max and show him all of the places that we loved so much and make new memories there with him.

This time around though, we decided to rent a villa rather than stay in a hotel – I hate being in a hotel and worrying about having a toddler disturbing other people’s stay. In a villa you are free to come and go as you wish, and make as much noise as you like. We found Casale dei Mandorli, a villa big enough to fit the three of us and my parents, located up in the Chianti hills, a short drive from Greve in Chianti.


Villa courtyard with table and chairs

View from infinity pool across Chianti


The villa itself was everything we could have hoped for – more than enough space for us all, and very tastefully decorated, but the really special bit was the stunning view from the garden across the tuscan hills. Making the most of the view was our very own infinity pool – so tempting on a hot day, but sadly we only managed to make use of it twice.


Infinity pool

Villa bedroom


The owners of the villa, Elena and Roberto, live onsite, in a similar villa next door, so was on hand if there were any problems. They also had a gorgeous spaniel, Boo, who Max really took a shine too – he can be a bit intimidated by bigger dogs, but Boo was the perfect size! And very patient with Max’s overexcitedness too.

The villa provided us with the perfect base to explore Tuscany – around halfway between Florence and Siena, and perfectly situated to explore all of the various Chianti hilltowns – San Gimignano, Volterra, Montepulciano, Montalcino, and Pienza. We planned to take things a bit easier this time with Max in tow, but still wanted to do a bit of exploring. We were brave (or foolish, depending on your view!), and didn’t take the pushchair with us, as we felt it was too much hassle to lug a car seat and a pushchair around at the airports, and Max doesn’t really like to sit in it, and certainly never sleeps in it. So we needed trips where we knew we would be able to park near the towns as we would likely be carrying a rather heavy two year old. We gave Florence and Siena a miss this time as we’d visited them so often in the past and focused on more of the smaller towns instead, so I thought I’d give you a whistlestop tour of them in photos!


San Gimignano

We’ve visited San Gimignano many times, and in fact is where John proposed to me (!), so we were always going to make a trip there. We stopped at the most amazing gelateria on the main square while Mum and Dad climbed to the top of the duomo and waved to us from the top. Max loved seeing Grandma and Grandad waving, and was very taken with the ice cream on offer and the amount of steps that the ancient Italians kindly put in to amuse the many children who might want to scale them.

The views from San Gimignano are amazing – make sure you follow the signs for the panoramicas, you won’t want to miss them!

Gelati in San Gimignano

View from San Gimignano



We visited the small but immaculate town of Pienza on our last visit and it felt like a great place to visit again. It was established by Pope Pius II as a utopian ‘new town’ and was the setting for Zefferelli’s Romeo and Juliet. It’s postcard perfect, with it’s cobbled streets, pretty floral displays, and views for miles. A highlight for Max was the small church, which he liked to walk into and then put his finger to his lips and ‘shh’. Oh, and lots of steps to climb of course!


Pienza - arches

Pienza houses with flowerpots

Peekaboo around the corner

Max and John


Fiesole is a tiny hilltop town just outside Florence, and it has the most stunning views you’ll get over the Florence skyline. It’s a bit of a hike up to the viewpoints, but amazingly Max managed to walk nearly all the way up the hill – he’s a determined little guy when he puts his mind to something! When you reach the top, the views are well worth it – there is a little church, a tiny shop to stop at for an ice-cream, and a few benches under some trees which provide a shady stopping point to sit and watch the busyness of Florence go by beneath you.


View from Fiesole

Fiesole - view from church

Florence skyline - duomo


Our week away just literally flew by – before we knew it, we were on the plane heading home. Next year I’m aiming for a two week break minimum!


Cuddle Fairy


Keep Calm and Carry On Linking Sunday
  • San
    June 14, 2016

    Amazing photos! I love Tuscany. It is where we had our wedding! Certaldo. We have been talking about going back this summer. You have just made me want to go more! 😀 love your blog! xxx @2littlefaces

    • Katy | Hot Pink Wellingtons
      June 15, 2016

      Ah, we visited Certaldo too, it was absolutely stunning! What a gorgeous place to get married! You should definitely do a revisit!

  • Cecile Blaireau
    June 15, 2016

    It looks amazing! Very nice pics. I am so jealous; I want to go too 😇 #BloggerClubUK

  • Rebecca Taylor
    June 15, 2016

    It looks amazing Katy!!! Stunning scenery and photos! And wowzers to the pool and its view! Glad Max loved it as much as you and John do! 🙂 x

  • Becky, Cuddle Fairy
    June 15, 2016

    You are killing me with this post! I would love to go to Italy someday. I hear Tuscany – then villa then Gellato!! My absolute favorite dessert. The different Italian towns are gorgeous. And the villa looks ideal! What a great holiday back at a nostalgic place. Thanks so much for sharing with us at #BloggerClubUK x

    • Katy | Hot Pink Wellingtons
      June 16, 2016

      Thanks Becky, we had such a lovely time, it was so hard to pick the photos! Should have split it into about 4 different posts but I think that’s probably excessive!

  • claire
    June 16, 2016

    I got married in Tuscany (Certaldo Alto) and we stayed on to honeymoon in Tuscany too. 5 years ago now but oh how I long to go back. We visited San Gimiginano (and the gelato place) too. Lovely photos.

  • Elena
    June 20, 2016

    Your pictures are so beautiful! I love Italy, I have been to many places there but not Tuscany. The last time we visited ,pre children, we went to Sorrento and the Amalfi Coast and the views were stunning

  • Jane Taylor
    June 21, 2016

    Oh, I love Italy! We have been to Lake Garda a few times but there are so many other places we want to visit. Your photographs are wonderful. I always love to see great photos in travel posts. The shot of the villa and its lovely brickwork and patio area with colourful pot plants is soooo appealing (as is the gelato!!!) I want to go!! #KCACOLS

  • Pickinguptoys
    June 26, 2016

    Oh how beautiful!Looks like a really gorgeous holiday x #kcacols

  • me and b make tea
    June 29, 2016

    Goodness it looks and sounds lovely. I remember going to Florence years ago and loving it. B would love the ice cream as much as Max I reckon haha! #KCACOLS

  • Madeline Littlejohns
    June 30, 2016

    Wow, that villa looks gorgeous! All your photos are gorgeous! I’ve not been to Tuscany, but we used to go to the South of France every summer when I was growing up and a lot of the photos remind me of the towns there, so I’m feeling a bit nostalgic now! x #KCACOLS

  • Emilie
    June 30, 2016

    It looks absolutely stunning! I went to Florence when I was 21 and travelling around Europe with my friend but I would love to do a holiday like this with my little family! #KCACOLS

  • Jenni - Odd Socks & Lollipops
    July 1, 2016

    Oh wow it looks amazing! Those blue skies! I am so jealous – I need to start looking at holidays! #KCACOLS

  • A Moment With Franca
    July 1, 2016

    Oh you are so lucky. What a beautiful place to visit! I have never been in Tuscany before but I would love to go. I have not been in Italy since I did a European Tour with my mum so many years ago. I love your photos. Your villa looks fantastic. And that infinity pool is just to die for. A shame that you couldn’t try it as much. I really need a holiday! Thanks so much for sharing this at #KCACOLS. Love having you here. I would love if you can also join us on the facebook group too, 🙂 xx

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