What Walking In Tuscany Is Really Like

Written by: Jan Osborne for Issue 10 of The Explorer magazine

Tuscany was as I expected it: picture-postcard perfect, with its rolling hills, cedar trees and panoramic landscapes. We started the week hiking along ancient pilgrimage routes, through olive groves, and rural houses. In the second half of the trip, the far-reaching fields changed colour as the soil changed to clay, replacing olive trees with grains, wheat and oats.

I’ve been on my own for 27 years and have had some wonderful adventures over those years – to Madagascar, China, Myanmar, Chile, Botswana – but always with friends. In October my companions and I took a trip to Tuscany for a Walking & Wine tour, and two things happened that took me by surprise. Firstly, it was my first walking holiday with Explore Worldwide and I absolutely loved it...

Walking in Tuscany as a solo traveller

Secondly, it gave me the courage to book my next trip as a solo traveller. If the truth be told, my holiday buddies booked the trip for me. We met years back on one of our Explore Worldwide adventures, and they have involved me ever since which has been brilliant.

I’m busy with the grandchildren and my own work, so they do the research, and I trust their choices. I’m a yes person so am always up for a different type of trip.

This one had three brilliant ingredients, the first being the destination. When my friends mentioned Tuscany, I just thought ‘how wonderful’ – I’d taken the kids camping there when they were small – a very different type of holiday of course but it had always been on my mind to return some day.

Read our solo travel guide for more top tips and practical advice

Walkers winding through Tuscany

How a Tuscany small group walking holiday works

As for the walking, I’m a member of a local group, and the well-designed hikes didn’t faze me – in fact, thanks to the cloudless skies we were so lucky to have had, it was the walks that turned out to be my idea of heaven. And the wine tasting was the icing on the cake. I enjoy my wine, but my tastes had always been limited to French wines, so I was certainly up for a re-education!

We were introduced to our group of 14 at our first hotel in Pisa. Four of us from the UK, two from Australia, and eight from Canada. I loved the diversity – I am a people person so found them all so interesting to chat to, whether that was at dinner, on the bus or side by side as we walked.

It was a mix of couples, two small groups, a mother and son, and a solo traveller. I took note how the solo traveller had done his research and had organised additional sights and activities ahead of time for our ‘reset’ days on the trip.

Discover how our Leisurely walking tours work

Montalcino, Tuscany, Italy

The types of walks we went on

On reflection, the hikes were not a stroll in the park – we must have walked a decent eight miles each day. But although most were gradual uphill climbs, the pace was leisurely, not breakneck. I never felt pressure to speed up, and the paths were good – we didn’t have to scramble or climb as such.

I think the length and the heat occasionally took its toll on some, but the views and the welcome we always got from the hilltop villages more than made up for the graft! Our hike on the third day took us through the countryside south of Castellina. It was our hardest walk at almost nine miles, but when I found it a challenge, I would just drop back, pause a while and start up again at a slower pace – there was no rush.

Our base for the next few days was also in a superb location for walking. We took on the ‘Gladiator hike’ the next morning, a panoramic loop that featured in the movie itself. And our final long hike before we headed to Florence was five hours of undulating trails and wide open views of Val D’Orcia. Oh, and a majestic picnic lunch that we just couldn’t finish!

This is how you prepare for a walking holiday

Beautiful Tuscany landscape with traditional farm house and hay bales in golden evening light, Val d'Orcia, Italy

Making time for food and cities

Florence by day, our last destination, was even busier than Siena, but we managed to escape the madding crowds for a sneaky gelato, and a 5pm hike to watch the sunset over the city – which was just breathtaking.

I can’t not mention the food. How do they do it? Simple, basic, earthy Italian cooking with the best ingredients. Every risotto I tried tasted different, and the lasagna was unlike any I had eaten. Laura was so helpful in recommending places to dine, and although we had the freedom to do our own thing, most evenings we ate together. One evening Laura took us to a butcher’s shop where we each chose a cut of meat. This was taken upstairs and cooked in the restaurant kitchen.

The mother and son duo, and two men in the group each chose a huge tomahawk cut, meant to be shared as a dish for two. This was incredible, two inches thick, barely cooked, and both pairs ate every mouthful. Apparently, this is a Tuscan speciality. It was a very interesting evening!

Siena, Italy