Cultural hiking in Italy: Tuscany trekking from Florence to Siena

Jun 19, 2018 BY Mark Pawlak

Interested in some cultural hiking in Italy? Then Tuscany trekking from Florence to Siena may be what you are looking for. Lovely trails through beautiful countryside, are combined with amazing buildings and more art, history and culture than you can shake your walking poles at!

Cultural hiking in Italy Tuscany trekking from Florence to Siena Flickr CC image by flöschen

Why go cultural hiking in Italy?

Of all the various modes of travel, by foot is the most intimate and also the most natural. Hiking allows you an often overlooked and underrated relationship with your surroundings.

Walking forces you to interact, take your time, and truly inhale the world around. Nowhere else on the globe are these intangible benefits more celebrated the famed Italian countryside of Tuscany.

From the artistic capital of the renaissance in Florence, to the Gothic cathedral spires in Siena. This sprawling region is characterized by rolling hills, storybook vineyards, and unbeatable authentic Italian culture and countryside. And the food and drink is not bad either!

Cultural hiking in Italy Tuscany trekking from Florence to Siena Flickr CC image of Florence by Mustang Joe

It is no surprise that Tuscany trekking routes have developed all over the region. They are now a must-do experience for active travellers seeking culture and countryside at their own pace.

Trekking from Florence to Siena

Begin in Florence, a city defined by art, religion, and timeless history. You’d need to stay a week to even begin to appreciate the masterpieces painted and adored here, let alone the food, monuments, and architecture that will make you wish your stay was longer.

The good news is that you won’t need to break the bank in Florence. As there are plenty of cheap hotels and hostels to stay in the city. So it’s well recommended to stay a few days before trekking from Florence to Siena.

Cultural hiking in Italy Tuscany trekking from Florence to Siena Flickr CC image of Florence by Ray in Manila

When you’re ready, set off on a southerly course over dusty roads bordered by grape and olive groves on your way to Colle Alta and the vineyards of Radda. Stop for overnight rest, refuel with local wine and cuisine and continue to the castle in Meleto and the stone village of San Donato.

The Chianti countryside is unmistakable. And you’ll find yourself pleasantly at home chatting with residents and exchanging stories with fellow travelers.

Saint Gimignano should be explored with care. The hilltop fortress village is famous for its stone towers and cathedral. Further south, stop off in Gaiole – the quintessential Tuscan town. Enjoy dinner and bed down at any one of numerous bed and breakfasts.

Cultural hiking in Italy Tuscany trekking from Florence to Siena Flickr CC image of Siena by Aderchen

Enter Siena on the final leg of your cultural hiking in Italy and visit Piazza del Campo in the center of town for dinner and drinks. Retire to your accommodation and congratulate yourself on a job well done. Perhaps plan a different route on your way back north?

Tuscany trekking

The best time to hike through Tuscany is in the summer and autumn. Besides olives and grapes, the landscape is colored with irises, poppies, and cypress trees. If you can take all of these in bloom you’ll really appreciate the beauty of the region.

There is not one specified trail or road to follow. Many options will lead to different villages and sites along the way. You can camp, but there is a huge range of accommodation available for all budgets along the way.

Cultural hiking in Italy Tuscany trekking from Florence to Siena Flickr CC image by francesco sgroi

The trek can take anywhere from 3 to 7 days depending on your pace and the route you choose. Of course you could take considerably longer if you want to!

We hope you enjoyed this guide to Italian cultural hiking in Tuscany. Be sure to check out our trekking holiday discounts as you could save a fortune on your next adventure.

Chianti, Colle Alta, Europe, Florence, Gaiole, Italy, Meleto, Radda, San Donato, San Gimignano, Siena, Tuscany
Hiking, Trekking
Affordable, Budget, Cheap, Cultural, Independent Travel, Low Cost
Travel Articles

    Related Articles


    Top 10 dropzones in Europe: Skydiving European style

    With more than 550 dropzones it is tough to decide where to skydive in Europe. But with many beautiful, historic destinations that ooze culture and throb with...

    Activities: Skydiving
    Destinations: Algarve Alvor Amsterdam +
    Read Article

    BSAC vs PADI: What is the difference in the scuba qualifications

    John Lennon once said that there were two types of people in the world: those who take showers and those who take baths. It’s pretty obvious that between writing...

    Activities: Scuba Diving
    Destinations: N/A
    Read Article

    20 best kite spots in Europe: Kitesurfing European style

    Kitesurfing European style is not some newfangled way of riding, it's about experiencing the continent and enjoying some epic kitesurfing. But with 66,000 kms of...

    Activities: Kitesurfing
    Read Article

    Newsletter sign up