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Walking holidays in Tuscany

Enjoy a non-group, self-guided walking holiday in Tuscany, walking either from one characterful hotel to the next while your luggage is transported, or from a single charming hotel. We provide you with our much-praised route notes, leaving you to set the pace and to decide how often you pause.
Walking holidays in Tuscany
+44 (0)1653 617001
Walking holidays in Tuscany
+44 (0)1653 617001

Walking holidays in Tuscany

– art, history & more
For a holiday that’s about more than walking, Tuscany is an obvious choice, offering an enticing blend of history, Renaissance art, food and wine. You’re not part of a group, meaning your time away is completely yours, so take time out to revel in the views and amble around hill-top towns. You can trust us to transfer your luggage, to choose accommodation of character, to provide precise route notes – and to make your walking holiday worth it.

New - Timeless Tuscany


 
Explore idyllic Tuscan countryside and medieval towns on this self-guided walking holiday, based at an enchanting 4-star hotel with easy access to iconic cities - the perfect getaway for 2027.

Iconic Tuscany | Walk along strade bianche, through sweeping countryside and olive groves.
Colle di Val d'Elsa | Your base for the week – a traditional town along the Via Francigena.
Elegant accommodation | Stay in the high-quality, comfortable Relais Della Rovere.
Varied walking | Either from the door or easily accessible by public transport.
Delightful day trips | Visit cultural hotspots like San Gimignano, Siena, and Florence.
  Discover Timeless Tuscany

Favourite Tuscan walking holidays

View all Tuscan walking holidays
View all Tuscan walking holidays

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The best walking in Tuscany

Given that the region lends itself to discovery on foot, pinpointing the best walking in Tuscany is not easy! For quintessential scenery of cypresses, vineyards and medieval villages, we recommend the area around San Gimignano. The far south is brimming with ancient Etruscan history, while our holiday from Bologna to Florence promises great contrasts and a real sense of journey.

For further ideas, see our full range of walking and cycling holidays in Tuscany.

How our walking holidays in Tuscany are graded

The undulating terrain means that walking in Tuscany usually involves a few ascents, but some of our walking holidays in Tuscany are easier than others, so you should familiarise yourself with our grades to ensure you choose the right holiday.
  • These gentle strolls range typically between 5-10km per day and involve few ascents or descents. Go at your own pace, pause at every opportunity, and take it all in.



    View all easy walking holidays
  • You don't have to be a seasoned hiker to enjoy these walks, but someone who's happy to take on around 5-15km each day – with the occasional hill thrown in.


    View all easy to moderate walking holidays
  • Expect to cover approximately 10-15km a day, across varied terrain with regular ascents and descents. You'll be challenged in places – but enjoy superb views.


    View all moderate walking holidays
  • Where rugged terrain goes hand in hand with the satisfaction of reaching a peak or high pass. Typically, days range between 7-20km and involve significant ascent and descent.


    View all moderate-to-challenging walking holidays
  • Our most thrilling walks involve full days on the trails, more challenging terrain, and testing ascents and descents, but there's still time to appreciate your surroundings.


    View all challenging walking holidays
  • Our flexible walking holidays give you a choice of routes each day, some of which are easier than others, so you can select the one that’s right for you on the day. This flexibility also makes these holidays perfect for anyone who is unsure of their level, or for groups of friends or family who want to enjoy a walking holiday together, but who may not all be at the same fitness level.

What to expect from your walking holiday in Tuscany

So that you enjoy them to the full, we ensure that all our walking holidays in Tuscany feature three essential ingredients: idyllic scenery; hand-picked accommodation of character where you’ll find a warm welcome; and delectable regional cuisine.
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