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Chianti Walking Holidays

Embark on a journey through the Chianti region, a land renowned for its artistic heritage, architectural marvels, delectable wines, and unique landscapes.
Starting point
Florence
Finish point
Siena
Duration
8 days / 7 nights
Season
April - October
Price
From: 1,085€/person
Difficulty
Leisurely to Moderate
Suitable for most people with basic stamina and walking experience

Traverse the awe-inspiring terrains of Tuscany and Chianti on foot

Delve into the abundant Renaissance heritage of Siena and Florence

Savour the exceptional local wines of the Chianti region

Trek through undulating hills, taking in the spectacular vistas of the ancient towns beneath

Leverage our meticulously designed itinerary and GPS routes to enhance your exploration

female hiker walking across tuscany hills

Hike through Tuscany's undulating hills

A man sipping a glass of Chianti wine with breathtaking views of Tuscany - Italian region famous for its picturesque landscapes and excellent wines -  ai generative

Savor world-famous Chianti wine with a breathtaking view

Chianti hills with vineyards and cypress. Tuscan Landscape between Siena and Florence. Italy

Explore enchanting landscapes and ancient Roman homesteads

Culinary delights in siena

Indulge in a leisurely feast amidst the charm of Siena

Woman is walking in a tuscan countryside

Immerse in Chianti's awe-inspiring beauty, one step at a time

Sunset view of Florence and Duomo. Italy

Witness the captivating sunset panorama over Florence

Siena city skyline, countryside and rolling hills. Tuscany, Italy

Soak in the timeless skyline of Siena, a medieval marvel

Uffizi Gallery. Piazza degli Uffizi square in the early Sunny autumn morning. Florence, Tuscany, Italy

Nourish your artistic spirit in the land of Michelangelo

female hiker walking across tuscany hills
A man sipping a glass of Chianti wine with breathtaking views of Tuscany - Italian region famous for its picturesque landscapes and excellent wines -  ai generative
Chianti hills with vineyards and cypress. Tuscan Landscape between Siena and Florence. Italy
Culinary delights in siena
Woman is walking in a tuscan countryside
Sunset view of Florence and Duomo. Italy
Siena city skyline, countryside and rolling hills. Tuscany, Italy
Uffizi Gallery. Piazza degli Uffizi square in the early Sunny autumn morning. Florence, Tuscany, Italy
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Included in price

Tour design and organisation

24/7 service and support during your holidays

GPS navigation with an easy-to-use app

7x accommodation with breakfast in 3* hotels

Luggage transfer

Transfers as per itinerary

From:
945€
/person

Seize this opportunity to embark on a captivating journey through Tuscany’s undulating hills, vineyards, and historic cities, nourishing your artistic spirit in the land of Michelangelo while exploring the enchanting landscape on foot.

The Chianti trail is the ideal way to experience the region’s most iconic landmarks, such as the medieval cities of Florence and Siena. Additionally, you’ll visit charming hamlets like Panzano and uncover ancient Roman homesteads nestled amongst the hills.

This walking tour features a meticulously designed itinerary highlighting the best of the Chianti region without feeling hurried or overwhelmed. You’ll indulge in a leisurely, well-paced walk each day, with plenty of time to delve into each location and absorb the scenery.

You’ll have the chance to sample some of the world-famous wines of the Chianti region, pausing at local wineries for a glass or two. The walking paths meander through forests and vineyards, offering awe-inspiring views, with your daily outings punctuated by visits to historical landmarks like the church of Santa Maria Novella.

And the cherry on top?

Our team handles every detail, from securing accommodations to providing GPS tracks for each route and a written guidebook to assist you. We offer round-the-clock support and coordinate transfers to ensure a seamless experience.

Unleash your adventurous spirit and immerse yourself in the awe-inspiring beauty of the Chianti region, where paradise awaits to be discovered and cherished!

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Start planning today!

The sooner the better - guaranteed availability and best prices if you don't wait for too long.

Things to know

Book now for guaranteed availability!

Start planning your trip as soon as possible. Flexible booking and Covid Refund Guarantee.
Inquire now

Self-guided

Those who like a good adventure and limitless flexibility should go on a self-guided tour. We prepare the itinerary and book your accommodations while 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.

TRIED & TESTED ADVENTURES

Only the best walking tours in Tuscany, cherry-picked by our 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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