Hiking in Tuscany: A Casual Guide for Walkers
Author : Lara Ehmler
22nd July 2025
From sun-drenched rolling hills to mediaeval villages, startling for their architectural beauty, hiking in Tuscany takes some beating. Every Autumn, our ‘supported’ self-guided walking holidays put hikers right at the heart of the heavenly Val d’Orcia, a UNESCO World Heritage site and – in our humble opinion – home to the best walking in the region. Our guests enjoy walks, researched and refined by us over many years, hand-picked accommodation with classic Tuscan hospitality, and the freedom to explore at their own pace.
Read on for a walker’s taste of Tuscany and hopefully you will be inspired to plan the perfect walking holiday in Italy’s Renaissance capital.
The Val d’Orcia: The best base for hiking in Tuscany
If there’s one place that encapsulates the soul of Tuscany, it’s the Val d’Orcia. Abundant with vineyards, olive groves, cypress trees, and chestnut groves, this is a joyful paradise for intermediate hillwalkers, who crave rolling landscapes punctuated by mediaeval castles and exquisite hilltop villages, rich with Renaissance architecture. It is no coincidence that one of the most photographed spots in Tuscany is the famous Val d’Orcia cypress trees near San Quirico d’Orcia, the nearest village to our base.
Unforgettable walks in Tuscany
We believe the Val d’Orcia to be the best springboard for hiking in Tuscany and, after many months of research and prevarication more than 10 years ago, we decided to make it a high-profile ‘off-season’ option for the many walkers who choose Collett’s year in year out. During our self-guided walking holidays, we provide you with the choice of a shorter walk and a longer hike. These itineraries – where possible – share the same trailheads, whilst showcasing the most exquisite landscapes of Tuscany, not to mention celebrated villages, such as Montepulciano, Pienza and Siena.
Discover The Walks
Our base in the Val d’Orcia
You will be staying at the charming Agriturismo Il Rigo, at the heart of a family-run working farm, owned and hosted by our friends Matthias and Luisa. It’s a beautiful location, where it is easy to relax and recharge your batteries. Attractive en-suite rooms are furnished with embroidered bed linen and antique furniture. But there’s more to Il Rigo than comfortable rooms and stunning views: Luisa is an award-winning pasta chef, and each evening she provides four courses of outstanding traditional Tuscan food, accompanied by wine from a local vineyard, which is likely to be world-renowned. You can expect sociable evenings with fellow Collett’s guests and also Walk Host(s), who are here throughout your stay to help you plan your walks, so you can enjoy your evenings with everything planned for the next day.
How to get to Tuscany?
Getting to Tuscany, and specifically the Val d’Orcia, is easier than you might think. We recommend flying into Pisa Airport, from where we offer weekly transfers (Saturdays) to your accommodation.
Rome is also a convenient gateway, with regular flights from the UK and elsewhere in Europe. From Rome, a scenic journey via train and bus takes you to the heart of the Val d’Orcia in under three hours.
This makes it incredibly easy to pair your walking holiday in Tuscany with a short city break in Italy’s historic capital. Imagine spending a couple of days exploring Rome’s ancient ruins and buzzing piazzas, then retreating to the peace and quiet of Tuscany’s countryside. It’s the best of both worlds!
The best time of the year to go hiking in Tuscany
Arguably, the season for walking in Tuscany could stretch from March to November, but we recommend avoiding the high summer months when high temperatures and intense sunshine can compromise the enjoyment of physically active days. Whilst spring is unquestionably a good choice, our favourite time is the Autumn when the vineyards come to life and the sun, now a little lower in the sky, casts a unique and heart-warming light on to exquisite landscapes. At this point, we have the absolute ideal conditions for hiking in Tuscany and, whilst there’s still a certain vibrancy to the villages, there is less tourist activity and more tranquillity.
Hiking in Tuscany during October
So we run our Tuscany walking holidays in September and October when the Val d’Orcia boasts its pastoral autumn glow. The vineyards turn into various shades of russet and gold, and the iconic winding cypress-lined roads provide the perfect backdrop for days on the trails. Everywhere you look, different hues of orange, brown and yellow reveal the inspiration of a thousand savoured watercolour paintings. It’s dreamy stuff for photographers too.
As for temperatures, they are now milder, averaging around 22°C during the day and 11°C in the evenings. It’s all very idyllic on many levels, whether you exploring labyrinths of mediaeval cobbled streets, observing the olive harvest, or soaking up the ubiquitous sweet aroma of roasted chestnuts. For walkers seeking authentic culture, quality walks, and inspirational repose, there’s no better time to visit.
The most scenic day hikes in Tuscany
One of the joys of hiking in Tuscany is the sheer variety of walks available. We provide you with a choice of two walks every day, one longer than the other. This is perfect for couples that like to vary their walks or smaller groups with different interests. All our walks unfold on recognised trails, including the renowned ‘strade bianche.’ Whilst all our routes have been carefully selected for their natural beauty, most walks will also feature special historic locations, such as the iconic hamlet of Bagno Vignoni famous for its hot springs and Roman baths.
Pienza & Capella Vitaleta
One of our favourite routes, and the opening walk of this holiday, takes you to one of the most iconic sights of the Val D’Orcia: The UNESCO World Heritage town of Pienza. Arriving in this exquisite medieval hill-top town in time for lunch gives you ample time to explore its historic and architectural treasures in the early afternoon, before marvelling at the rolling hills of the Val d’Orcia on the way home. Back at your accommodation, you can join us for a complimentary wine tasting. Enjoy the world-beating wine that came from the vineyards you traversed that very day!
Walk with confidence
During a Collett’s self-guided holiday we will provide you with detailed route notes, maps, and smartphone GPS navigation, so you can explore with confidence. the icing on the cake is our small local Walks Team, which is on-hand at your accommodation to welcome you on arrival and provide daily support and insider knowledge. You’ll feel like you have a local friend in Tuscany, someone to help tailor your experience and make every walk more rewarding.
To get a flavour of what our guests think of these experiences, read our guest interview, where one of our first-time guests, Anne, shares the special sentiments of her memorable Tuscan adventure.
Read The ReviewExperience Tuscany With Collett’s
Our self-guided walking holidays in Tuscany are about more than just beautiful hikes, they’re about slowing down, soaking up the atmosphere, and enjoying exquisite cuisine and culture. You set the pace, we take care of the details.
