Background Image

Tuscany Walking Tours

Stroll through Tuscany’s timeless landscapes, where rolling vineyards meet historic towns, and every walk ends with a glass of Chianti and a taste of Italy.
  • Relaxed walking routes through vineyards and olive groves
  • UNESCO-listed towns like Florence and Siena, embodiments of Renaissance
  • Tuscan culinary delights, from artisan cheeses to famous Chianti wines
  • Slow-paced exploration of Tuscany’s lifestyle in rustic villages
Product Image
Product Image
Product Image
Product Image
Product Image
Product Image
Product Image
Product Image
Product Image

Via Francigena Highlights

9 days1/53/5

Discover the enduring allure of Tuscany along the historic Via Francigena, taking you through scenic vistas, quaint villages, and towns recognized by UNESCO.

From 1199€/person
More
Product Image
Product Image
Product Image
Product Image
Product Image
Product Image
Product Image
Product Image
Product Image

Montepulciano to Siena Walking Holidays

9 days1/53/5

Discover the serene beauty of Italy's core on a journey from Montepulciano to Siena, a captivating trek through historic towns and picturesque scenery.

From 2289€/person
More
Product Image
Product Image
Product Image
Product Image
Product Image
Product Image
Product Image
Product Image
Product Image
Product Image
Product Image
Product Image
Product Image

The Ultimate Liguria & Tuscany Hiking Tour

14 days2/53/5

Explore Cinque Terre, Liguria, and Tuscany on a two-week hiking tour, discovering coastal villages, historic cities, and scenic trails from Genoa to Florence.

From 2890€/person
More
Product Image
Product Image
Product Image
Product Image
Product Image
Product Image
Product Image
Product Image
Product Image
Product Image

Chianti Trail Tuscany Walking Tour

8 days2/52/5

Stroll the land of artistry, finest architecture, savory wine, and heavenly landscape on this walking tour across the Chianti region of Tuscany.

From 1085€/person
More
Product Image
Product Image
Product Image
Product Image
Product Image
Product Image
Product Image
Product Image
Product Image

Walking Holidays in Tuscany and Umbria

10 days2/53/5

Experience the soul of Italy by walking through its scenic vineyards, visiting ancient towns, and indulging in regional treats in both Tuscany and Umbria.

From 2399€/person
More
Product Image
Product Image
Product Image
Product Image
Product Image
Product Image
Product Image
Product Image
Product Image

Luxury Walking Holidays Tuscany

8 days3/53/5

Indulge in the lap of luxury with our carefully crafted self-guided walking holidays in Tuscany's lesser-known treasure, the Garfagnana Valley.

From 2575€/person
More
Background Photo

Why Visit Tuscany on a Hiking Tour?

Tuscany is the epitome of the Italian “La Dolce Vita,” the sweet life one experiences through incredible cuisine, rich flavors of Italian wine, and cultural beauty.

Its rolling hills are the perfect backdrop for the breathtaking architecture of Florence, Siena, and Montepulciano, known as living galleries of Italian heritage, with each corner echoing stories of artists, philosophers, and farmers who shaped the region.

While Tuscany may not immediately strike you as a conventional hiking destination, this slower-paced realm allows you to feel Italy in every footfall, making it a perfect blend of internal reflection and external discovery.

From the famous Via Francigena pilgrimage route to hidden paths through the Garfagnana region, every step through vineyards, olive groves, and quaint villages (and every bite you take along the way!) brings you closer to unlocking Italy’s rural heart.

Each corner you turn will make you fall in love with the region. Think rustic farmhouses, agriturismi, and boutique hotels enveloped in divine smells of pomodoros and basil waiting for you to enjoy a glass of world-class wine on a sunny evening after a day of exploration.

Although summer might be too hot for prolonged walks, spring and early autumn are ideal for uncovering Tuscany’s beauty. In more rural regions, public transport may be limited.

Still, the slower pace of hiking, combined with easy access to local highlights, makes it the perfect way to explore Tuscany’s charm without rushing.

Frequently Asked Questions

Of course. We aim to make your decision as easy as possible. Therefore, we crafted several selections targeted at particular groups of hikers – Best for Beginners, Best for Advanced Hikers, Mountain Hikes, Pilgrimages, Classic Treks, etc. 


If you remain unsure and overwhelmed, you can fill out this form or book a call with us, and we can help you directly.

Agent picture
Samo
Talk to our travel expert
info@hiking-tours.com
+14782496098
Book a Free Consultation
Usually replies within 1 hour!
Andrew Luff's profile photo

Andrew Luff

Verified customer

A fantastic 3 day self guided Hut to Hut hike around Triglav National Park in Slovenia. We experienced a full range of weather which made it an unforgettable trip. The organisation and back up support with GPS maps etc was excellent. Hut staff were friendly and very happy to give advice and suggestions on the routes and directions. Would recommend.

Review 1
Review 2
Review 3
Carly Leonard's profile photo

Carly Leonard

Verified customer

My friend and I went with Triglav Tours for a 3 day, 2 night hike this summer and had the most amazing time!! Our guide, Bine, was awesome and had lots of cool facts to share about the area we were hiking. Additionally, my friend and I had not completed such a technical hike before and the guide and other guests were very patient with us and encouraging, ensuring we felt safe the entire time. The overnights were also such a fun way to get to know Bine, the other guests, and other hikers as well. Cannot recommend Triglav tours enough!!!

Review 1
Review 2
Review 3
Michael White's profile photo

Michael White

Verified customer

I arranged a six-day/five-night trip with Hut to Hut Slovenia. It's the first time I've gone with a tour organizer and I can say it went really well. In the past I've arranged huts myself and it is a huge hassle figuring out how to make the bookings, if the bookings actually exist, and what good/viable routes might be. Having this all sort was, at least to me, totally worth it. The routing is via Ride with GPS, which was great. I'd recommend bringing 1:25,000 scale paper maps as a backup, just in case. The huts themselves differ wildly. Some are really rustic with, ahem, interesting toilet facilities. One was accessible by road and thus had showers, a long menu, and even espresso. All will have some sort of food, but you might only have two options for dinner (one with meat, one vegetarian). The cuisine in the Slovenian huts leans strongly to stews and goulashes with minimal fresh vegetables and/or fruit. Certainly good and hearty but pretty much everyone I talked to said the food was better in the Italian and Austrian huts. Some huts are cash only, some take cards (but the card reader might be down). A 1.5 litre bottle of water is about 6 euro, so if you have a beer with dinner and also buy lunch you need to carry about 25-30 euro per day in cash (assuming you have a booking that includes breakfast). Of the six days of hiking, four were ridiculously spectacular, with the highlight being sunrise from Mt Stol. Getting up to the high mountains, though, can be crazy steep, with switchbacks only sparsely used. Descents are similarly tough, and you have to watch every step. For the first time ever I used trekking poles and my knees thank me. Two days were a bit of a slog, but this is probably unavoidable getting up to or down from the high terrain. Would I do something like this again? Yes, absolutely! But next time it will probably be the Dolomites.

Review 1
Review 2
Review 3
Roman Klymenko's profile photo

Roman Klymenko

Verified customer

Very beautiful hike. I did not expect that Slovenia is so amazing.

Review 1
Review 2
Review 3
Birgit Kindler's profile photo

Birgit Kindler

Verified customer

We had a lovely hike today with our guide Klemen. He personalized the tour on our needs and interests, so that we saw places we wouldn't without his experience. The hike was a little bit slippery after the rain from the last days and it went a lot upwards, but it was totally worth it! Thanks again :)

Review 1
Review 2
Review 3
Dominik Schrotter's profile photo

Dominik Schrotter

Verified customer

We had a great day with Klemen on this hike, he showed us some lesser known spots/highlights of the southern part of the julian alps with a nice viewpoint at the end. 10/10 would book again

Review 1
HANDPICKED ADVENTURES

HANDPICKED ADVENTURES

Only the best adventures across the world, cherry-picked by our team with an in-depth knowledge of the regions.
VALUE YOUR TIME

VALUE YOUR TIME

With everything on your plate, let us handle the vacation planning, so your valuable time stays exactly where you need it.
SELF-GUIDED TRAVEL

SELF-GUIDED TRAVEL

Explore independently and with confidence while we keep everything running from behind the scenes.
TRUSTED BY MANY

TRUSTED BY MANY

Since 2014, we have taken care of thousands of happy customers, making it our mission to put your satisfaction first.
OUTDOOR SPECIALISTS

OUTDOOR SPECIALISTS

We are a team of outdoor specialists equipped with the knowledge and insight to bring you the best hiking experiences.