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Chianti Trail Tuscany Walking Tour

Stroll the land of artistry, finest architecture, savory wine, and heavenly landscape on this walking tour across the Chianti region of Tuscany.
Starting point
Florence
Finish point
Siena
Duration
8 days / 7 nights
Season
Apr - Nov
Price
From: 945€/person
Difficulty
Leisurely to Moderate
Suitable for most people with basic stamina and walking experience

Experience the breathtaking landscapes of Tuscany and Chianti on foot

Immerse yourself in the rich Renaissance history of Siena and Florence

Indulge in the exquisite local wines of Chianti

Walk across rolling hills, enjoying stunning views of the medieval towns below

Take advantage of our expertly planned itinerary and GPS tracks to maximize your adventure

Culinary delights in siena

Taste the flavors of Tuscany in historic Siena with us

Tuscany

Wind through vineyards for world-renowned wines

Florence and arno river

Admire Florence on foot, an iconic part of your tour

Finest chianti wine

Savor Chianti's wines, your glass awaits

Medieval siena

Take in Siena's grandeur, part of your well-paced walk

Cypress tuscany

Traverse cypress-lined roads, an iconic Tuscan view

Tuscan cuisine

Relish Tuscan cuisine

View of siena

Explore Tuscany's beauty

David

Feed your artistic soul in the land of Michelangelo

Included in price

Tour design and organization

24/7 service and support during your holidays

GPS navigation with an easy-to-use app

7-night accommodation with breakfast in 3* hotels

Luggage transfer

Transfers per itinerary

Here is your chance to embark on an immersive journey past Tuscany’s rolling hills, vineyards, and historic cities, feeding your artistic soul in the land of Michelangelo while exploring the magical landscape on foot.

Walking holidays in Tuscany is the perfect way to see the region’s most iconic landmarks, such as the medieval towns of Florence and Siena. In addition, you will visit quaint villages, such as Panzano, and discover ancient Roman farmsteads hidden amongst the hills.

This walking tour has a carefully planned itinerary that showcases the highlights of the Chianti region without feeling rushed or overwhelmed. You will enjoy a relaxing, well-paced walk each day, with ample time to explore each location and take in the scenery.

You’ll have the opportunity to taste some of the world-renowned wines of the Chianti region, stopping at local wineries for a glass or two. The walking routes wind through forests and vineyards, offering breathtaking vistas with your daily excursions punctuated by visits to historical landmarks, such as the church of Santa Maria Novella.

And the best thing of all?

Our team takes care of every detail, from booking accommodations to providing GPS tracks for each route and a written booklet to guide you. We offer 24/7 support and coordinate transfers to ensure a hassle-free experience.

Join our walking tour in Tuscany and grab a little piece of heaven on Earth to take back home with you.

Location

Things to know

Join a Group

For solo hikers or hikers who wish to meet other like-minded souls, and don’t want to stress about tour-planning and other annoying details. We’re going to find you a group of like-minded outdoor enthusiasts and take care of all the other details. The tour will be led by our guide, who’ll make sure everything runs smoothly, ensuring maximum hiking enjoyment.

Private Guided Group

Experience the great outdoors on a private guided tour tailored just for your group. It’s for those who want a hassle-free adventure and enjoy the flexibility of a small private group and not stress about the details of everyday planning. The guide will be fully at your disposal to make this experience as personalized as possible, maximizing enjoyment during and after the tour.

Self-guided

Those who like a good adventure and limitless flexibility should go on a self-guided cycling holiday in Slovenia. We prepare the itinerary and book your accommodations; You enjoy the journey without our guide, being fully in charge of all the daily decisions. While you’ll have the full support of our team in case of any emergencies or concerns, a certain level of self-reliance is required.

Hassle-Free

We handle itineraries, accommodations, and anything else you prefer not to deal with, so you can enjoy a carefree hike.

Trusted by Many

We are a financially protected company, fully bonded and insured, keeping your money safe and allowing you to travel with confidence.

Handpicked Adventures

Only the best walking tours of Italy, cherry-picked by our local team with an in-depth knowledge of the region.

Unbeatable Support

Our 24/7 customer support is where we show our passion, bringing you a better experience by making your well-being our number one priority.

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