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Bucket list | The dream of a villa holiday in Tuscany

By Rebecca Miles – 31st July 2020

It’s hard to beat the romance of Tuscany. Those distinctive cypress trees, the warmth of the sun turning the rolling hills shades of orange and pink, the ancient hilltop towns with their towers and imposing walls, and of course the food and drink. Deservedly famous for its olive oil, truffles and simple but delicious salamis and ham, I could wax lyrical about languid days grazing from long lunches to bacchanalian dinners for hours.

The pool at Pinolo, surrounded by olive trees in the rolling hills of Tuscany
The pool at Pinolo, surrounded by olive trees in the rolling hills of Tuscany

But how does all that work when you throw children in the mix? Does the lure of a week’s villa holiday in Tuscany still stand? Can you enjoy the sheer charm of the place when you bring the family along?

If you’re short on time, I’ll save you the long read: the answer is yes. If you’re thinking I like the sound of a family holiday there, read on.

Italy has a well-deserved reputation for its family friendliness – restaurants positively welcome children, and children are allowed and encouraged to be children, and Tuscany is no exception.

We were seriously tempted, but as with all precious family holidays I was worried about getting it wrong, so spoke to Daniel Wrightson, owner of Invitation to Tuscany.

His family set the company up in 1982, and it specialises in holidays to Tuscany and more recently Provence. Dan knows all his accommodation inside out, and he prides himself on his rule – if his family feels uncomfortable in a villa (say, worried about spilling olive oil on the table), he won’t list it.

Casole d'Elsa sits on top of a hill surrounded by Tuscan countryside
Casole d'Elsa sits on top of a hill surrounded by Tuscan countryside

When I explained what we were looking for and who we were (me, my husband and our three-year-old daughter Evie, wanting to spend the week relaxing and exploring the quieter side of Tuscany), he suggested several different properties, each perfect in different ways.

But he also threw in a curveball suggestion. Because we were travelling in low season September, he suggested we spend most of our week in a villa with a pool, walking distance to a hilltop town, but also have a few nights in Dan’s House, an apartment – with no pool – built into the historic walls of the same hilltop town.

Initially hesitant – I’d been dreaming of a pool, they’re so central to a villa holiday – Dan sold it to me with the promise of idyllic river swimming nearby, the buzz of the town with its bars, restaurants and art galleries, and one of the region’s best gelateries a few minutes’ walk away. Evie would love that.

She also, more than we appreciated at the time, LOVED that the hilltop town was called Casole d’Elsa. “We’re going to stay in Elsa’s town?”, she’d regularly ask. Which Frozen-loving child couldn’t help but be excited about that.

A sculpture of faces enjoying the views from Casole d'Elsa
A sculpture of faces enjoying the views from Casole d'Elsa

Casole d’Elsa was a particularly prominent town in medieval times as it was on the route from Canterbury to Rome. It’s hard to imagine now, but Tuscany was a brutal region with warring families constantly at battle – hence all the heavily fortified, stone-walled hilltop towns which now look so picturesque but were actually built out of fear and protection.

Pirates roamed the coast, so travellers headed for Rome followed the river one valley inland, the Elsa valley, instead. Casole d’Elsa did have a tower, but it was destroyed after a conquest and the townspeople never got round to rebuilding it.

It’s no loss, the town is an interesting place to potter around and we quickly settle into apartment life in its centre.

Built into the thick old stone walls of the town (the bathroom makes a brilliant feature of them), Dan’s House is wonderfully cool – both climatically and stylistically – and its views from the terrace and the tall windows stretch across the valley.

It’s a joy to open the front door on to some terracotta steps leading up to the main street, and we love how easy it is to join in the evening’s passeggiata, picking up ice creams from Gelateria La Torre to eat while watching the sun set from the town’s walls before heading for a spritz at Caffè Casolani and dinner at Dal Brigante.

The next day is hot, so we take Dan up on his suggestion of river swimming. It’s not something I’ve done much of before but he assures us he’s sending us to a safe spot.

We buy delicious sandwiches for a picnic lunch from the Bottega di Casole deli and drive for about 20 minutes to the Riserva Naturale Alto Merse just beyond Brenna. There’s a car park by a bridge among the trees and we follow our noses along a path heading upstream.

The river is dappled with shade and a few metres wide with shallow banks and big boulders. Around a bend, two women are merrily breast-stroking through the water; it looks so inviting. We walk on some more until we find an ideal picnic spot under a tree next to some shallow stepping stones. Hundreds of tiny fish swim about, as dragonflies buzz around and a frog hops into the shade.

It’s bliss. We start with a gentle paddle before splashing among the shallows and venturing out into the deeper pools created by the large rocks and boulders – the water is fresh, and getting my shoulders under takes my breath away, but in the heat the shock is worth it.

The river is only a metre or so deep and we swim out to a mini limestone island with perfectly placed ledges for jumping off. It’s so much more picturesque than a swimming pool would be and feels like a proper adventure. If river swimming is always like this, we’re sold.

Back in Casole d’Elsa, we take a stroll around the town before dinner. There’s plenty to see (and at least two playgrounds), as well as several inviting bars. Over the years, artists have flocked to Casole and there are several galleries and artisan workshops as well as lots of sculptures and large works of art spread around the parks and squares, hidden down inviting alleyways and tiled on the streets’ walls. I fall in love with an intricate bronze tree by Andrea Roggi and am over the moon when I spot a mini version in one of the galleries, but with a price tag of €3,500 it’ll have to go to someone else.

The following day we move all of a five-minute drive to our villa with a pool, Pinolo. It’s part of an old farm house set among olive trees and is one of three apartments available to rent.

It’d be great to stay there with a couple of other families – in total there are five bedrooms and plenty of large terraces outside to share, as well as, of course, the pool – but in September it’s quiet and we largely have the place to ourselves.

And the pool – at last, that bliss of lying on a lounger next to a sparkling pool, jumping in to cool down on a whim, and splashing and floating around. But is it any better than swimming in the river? Not necessarily – yes it’s more convenient, but the wild freedom of the river has its own appeal.

The pool at Pinolo - as inviting as it looks
The pool at Pinolo - as inviting as it looks

While staying at Dan’s House, we’d got into the habit of going out for breakfast, feeling ever-so-cosmopolitan as we ordered our cappuccinos, pastries and juices at Bar Montomoli, so we continue this at Pinolo, making a morning of it with a 20-minute walk in, a leisurely breakfast, picking up supplies from the Bottega for lunch back by the pool and stopping at the playground both there and back. It feels wonderfully relaxing to dip in and out of the town, knowing we have an afternoon of lazy eating and sunbathing ahead of us.

Where we particularly miss Dan’s House and it’s stylish convenience is at spritz time for the buzz of the passeggiata, and we can’t just pop out for an ice cream. But having a peaceful drink on the large terrace overlooking the valley is hardly a hardship, and it’s great to experience both.

No holiday to Tuscany would be complete without a day trip to at least one of the headline cities of Siena, Florence and Lucca. Their history, cultural significance and beauty are renown, but are they worth visiting with a three-year-old?

Siena is closest to us – and I have fond memories of visiting in my late teens, so with light showers forecast one day deterring us from the pool we head there.

It’s a warren of narrow streets winding up and down and around and the entire city centre has been declared a UNESCO World Heritage Site. The maze of streets regularly open up into vast piazzas, the most famous of which is the Piazza del Campo, home to the legendary twice-annual horse race, the Palio.

A lawless, anything-goes race dating back to medieval times, 10 riders race bareback around the piazza, each fiercely representing one of the city’s contrada (or wards). Each contrada has its own emblem and colours, and it’s fun to wander around and try to spot the eagles, owls, dragons and uniorns, among others, decorating the walls of the city.

Standing in the centre of the shell-shaped Piazza del Campo, with the imposing Torre del Mangia leaning over us, we play at horse racing, cantering around the square and chasing each other. The tourist office had been playing a video of the Palio, and Evie was fascinated.

Other than that, the tourist office drew a blank for us. When asked what they recommended for children, I got an Italian shrug of the shoulders. Siena is bursting with cathedrals and museums, but they’re not aimed at children (are we just spoilt for child-friendly museums in the UK?), so instead the woman directs us to a park within the city walls, and a playground just behind the Piazza del Campo.

But we’re quite content following our noses, popping into interesting looking shops (Siena has a lot of local artisans making quirky crafts) and eating ice cream.

Lunch is a sacred part of our holidays so in Siena, with its many tavernas and osterias, I had expected we’d settle down somewhere picturesque and eat some fabulous local dishes. Instead, walking down a seemingly nondescript road, we come across Pizzeria San Martino, a small takeaway pizzeria with a few seats inside and it’s one of those places that just leaps out as perfect for now. It’s authentic – local office workers are queuing for their lunch – and friendly, and has a huge variety of pizza slices ready to go, priced at €1-2. Glasses of wine are poured from large barrels behind the counter and we grab a few stools in the corner for one of the best lunches of our holiday.

Siena may not have been the cultural highlight I was expecting, but it’s been fun to roam the streets and we buy some memorable souvenirs and presents before the lure of returning to our own pool wins out.

As with lunch in Siena, our holiday in Tuscany wasn’t quite the hazy lazy retreat I was expecting, but as with so many things with children the reality was so much better than my imagination. We soaked up the romance of the place, fed and watered extremely well, and were in a happy holiday bubble. Also, hopefully, with the bonus of staying in ‘Elsa’s town’, we’ve encouraged Evie to want to return again and again. And that’s something I’m very happy to do.

The details

We travelled to Tuscany in September 2019. The current situation in Tuscany is everything has reopened and as of 1st July there are no cases of the virus. Wearing masks is required in enclosed public spaces and don’t be surprised if you’re required to have your temperature checked. We’d highly recommend booking now for next summer. 

Getting there

We flew with British Airways to Pisa and hired a car. Casole d’Elsa is about a 90-minute drive from Pisa airport.

Where to stay

Invitation to Tuscany has a wonderful selection of villas and apartments, hand-picked by Daniel Wrightson and his family. We stayed at Dan’s House, in the centre of Casole d’Elsa, and Pinolo, a 20-minute walk from the centre of Casole. Both sleep four in two bedrooms. Prices for Dan’s House start from €800; Pinolo starts from €845 for a week’s self-catering. For more information, visit Invitation To.

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