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  • Monday - Friday9am - 5pm
  • Saturday9am - 1pm
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Walking and Hiking Holidays in Tuscany

Book early and pay less: save £40pp when you book six months ahead

View all walking and hiking holidays in Tuscany

Explore and discover the beauty of Tuscany. It is located in central Italy where you will find well known cities such as Florence, Siena and Pisa. Tuscany is renowned for its picturesque landscapes, historical architecture and amazing art. Indulge in the local Tuscan cuisine and enjoy a wine tasting in the stunning vineyards and have a glass of wine - or two!

Walking and hiking holidays in Tuscany are the perfect way to take in all the views and trek by foot through the historical towns and countryside. Step back in time and visit Siena an venture around Monteriggioni to get the taste of historic Tuscany. Perfect for travellers who want to absorb the culture and learn more about the mediaeval buildings.

Discover how to make a classic Tuscan dish and try some delicious red wine during a wine tasting experience. Tuscan red wine is well-known and loved. You can visit an olive farm for a light lunch and olive oil tasting. This is definitely an experience that will tickle your taste buds.

Travel away from the Tuscan towns and experience a walking tour of the Garfagnana Valley. Perfect for those who love beautiful landscapes and would enjoy exploring the World Heritage Site of Cinque Terre.

Popular walking and hiking holidays in Tuscany

Adagio
Tuscany's Treasures

Tuscany's Treasures

Departure dates

  • 2025:
    • Sep
    • Oct
  • 2026:
    • Apr
    • May
    • Sep
    • Oct

A taste of Tuscany - food, wine, art, history and scenic landscapes, Tuscany is a delight for all your senses. Enjoy wine and olive oil tasting in Montecatini Alto, and cook your own Tuscan dinner at a local farm!

Grade Leisurely
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Our holiday walking grades

Leisurely

Grade 3

We still class this level as leisurely; walks are generally a little longer than level 2, with undulations but over a longer distance. Where sightseeing distances are longer, we take a full day with opportunities to stop, rest and refuel. Generally, itineraries involve easy countryside walking with plenty of breaks.  

Search all Leisurely, Grade 3 walking holidays

Usual daily walks - Distance: 4 miles; Ascent/Descent 300m; Terrain: generally good paths and tracks; Walking Time: Half Day or Full Day walks. 

Food & Wine
From £1,989
7 Nights
With flights
View Details
Self-Guided
Tuscany: A Journey Through the Chianti Region (Self-Guided)

Tuscany: A Journey Through the Chianti Region (Self-Guided)

Departure dates

  • 2025: Jul - Oct

Explore the brilliance behind "Chianti Classico and Gallo Nero" wines by strolling through the picturesque vineyards where they originate. Nestled between the thriving art cities of Florence and Siena, the Chianti region unveils its natural splendour and unparalleled culinary treasures.

Grade Moderate
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Our holiday walking grades

Moderate

Grade 4

Usually, your walk will take up the whole day at a moderate pace. Terrain will often be hilly and paths generally good. Note that on holidays in mountainous areas, expect some rougher paths. An average walk length is 6 miles but expect this to vary from as little as 3 miles on a sightseeing day and up to 10 miles on a full day dependant on the amount of ascent and decent required.

Search all Moderate, Grade 4 walking holidays

Usual daily walks - Distance: 6 miles; Ascent/Descent 500m; Terrain: sometimes hilly and undulating on good paths and tracks; Walking Time: Day walks. 

Culture
From £1,029
7 Nights
Tour only
View Details
Self-Guided
Via Francigena - From Lucca to Siena (Self-Guided)

Via Francigena - From Lucca to Siena (Self-Guided)

Departure dates

  • 2025: Jul - Oct

Walk the famous Via Francigena through the Tuscan countryside from Lucca to Siena accompanied by vineyards, hill-top villages and rolling landscapes

Grade Challenging
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Our holiday walking grades

Challenging

Grade 6

Full day walks with appreciable amounts of ascent and descent and longer distances covered.  Whilst you will be mainly on paths, these may be rough, steep, and loose at times. We take the whole day to enjoy some fabulous walks.

Search all Challenging, Grade 6 walking holidays

Usual daily walks - Distance: 8 miles; Ascent/Descent 850m; Terrain: sometimes rough, loose or steep sections; Walking Time: 8hrs / Full Day walks. 

Pilgrimage Routes
From £859
7 Nights
Tour only
View Details
Classic
Apuans & Apennines

Apuans & Apennines

Departure dates

  • 2025:
    • Aug
  • 2026:
    • Jun
    • Jul
    • Aug
    • Sep

Nestled away from the Tuscan tourist trail, a secluded valley, guarded by a horse-shoe of mountains, invites exploration. Discover the captivating allure of the Apuan and Apennine ranges, hiking through Italy's diverse landscapes. This harmonious blend of scenic vistas and cultural richness offers an unforgettable journey through picturesque Italian mountain terrain.

Grade Challenging
Close

Our holiday walking grades

Challenging

Grade 6

Full day walks with appreciable amounts of ascent and descent and longer distances covered.  Whilst you will be mainly on paths, these may be rough, steep, and loose at times. We take the whole day to enjoy some fabulous walks.

Search all Challenging, Grade 6 walking holidays

Usual daily walks - Distance: 8 miles; Ascent/Descent 850m; Terrain: sometimes rough, loose or steep sections; Walking Time: 8hrs / Full Day walks. 

Landscape
From £2,299
14 Nights
With flights
View Details
Self-Guided
Tuscany: A Journey Through the Chianti Region Short Break (Self-Guided)
  • What's NewWhat's New

Tuscany: A Journey Through the Chianti Region Short Break (Self-Guided)

Departure dates

  • 2025: Jul - Oct

Explore the brilliance behind "Chianti Classico and Gallo Nero" wines by strolling through the picturesque vineyards where they originate. Nestled between the thriving art cities of Florence and Siena, the Chianti region unveils its natural splendour and unparalleled culinary treasures.

Grade Moderate
Close

Our holiday walking grades

Moderate

Grade 4

Usually, your walk will take up the whole day at a moderate pace. Terrain will often be hilly and paths generally good. Note that on holidays in mountainous areas, expect some rougher paths. An average walk length is 6 miles but expect this to vary from as little as 3 miles on a sightseeing day and up to 10 miles on a full day dependant on the amount of ascent and decent required.

Search all Moderate, Grade 4 walking holidays

Usual daily walks - Distance: 6 miles; Ascent/Descent 500m; Terrain: sometimes hilly and undulating on good paths and tracks; Walking Time: Day walks. 

Culture
From £719
4 Nights
Tour only
View Details
See all holidays in Tuscany

Why book a walking or hiking holiday in Tuscany?

Booking a walking or hiking holiday in Tuscany is one of the best ways to experience this enchanting region of Italy. On foot, you can witness the rolling hills, verdant vineyards, and timeless villages unfold before you, captivating both heart and soul.

Our dedicated team of travel experts designs incredible hiking and walking experiences that showcase the extraordinary natural beauty and historic charm Tuscany offers, along with its hidden treasures.

Join our knowledgeable guides and embark on adventures along stunning trails scented with wildflowers and olive groves, where they share their immense understanding and passion for this storied region.

Booking one of our curated holidays means less hassle, as we take care of your flights, accommodation, and travel arrangements in Tuscany, leaving you free to soak up the stunning landscape.

Collaborating with local experts and experienced guides, we offer unique, authentic hiking escapes that provide an unforgettable glimpse into Tuscany's rich culture and natural splendour.

Highlights of walking in Tuscany

Stroll Through the Charm of Florence and Siena

Exploring Florence and Siena on foot allows for a relaxed journey through these historic cities. In Florence, stroll through its Renaissance heart, taking in the remarkable art and architecture. In Siena, each step along its medieval streets reveals new discoveries, from the majestic Piazza del Campo to hidden artisan shops.

Unwind Amongst Chianti’s Vineyards

The gentle walking trails of Chianti guide you through some of the most picturesque wine country in the world. With a delightful path meandering through vineyards and olive groves, you can savour wine tastings at a leisurely pace, pausing at family wineries to appreciate the rich flavours. The serene paths between Greve and Radda in Chianti offer a peaceful escape into Tuscany's lush landscape.

Discover Fiesole’s Scenic Views

A short walk from the bustling city of Florence leads to Fiesole, where ancient trails reveal panoramic vistas. The gentle paths around this charming hill town, home to a Roman amphitheatre, provide an ideal setting for a relaxed exploration. Enjoy a leisurely walk that opens up views over the Tuscan countryside, combining the beauty of nature with historical intrigue.

Explore our walking holidays in Tuscany

Highlights of hiking in Tuscany

Ascend Majestic Peaks and Trails

In the heart of Tuscany, hiking enthusiasts are invited to ascend the Pania di Corfino for breathtaking panoramic views of the Apuan Range.

The journey up Pania della Croce, celebrated as the Queen of the Apuans, offers a remarkable hiking experience, suitable for various skill levels, and rewards adventurers with sweeping vistas.

For those seeking a captivating trail, the '00' footpath along the Tuscany-Emilia Romagna watershed presents fantastic views of the Apennines, the Apuan Alps, and the serene beauty of the Garfagnana Valley.

Explore Diverse Landscapes and Scenic Gorges

Hiking through the newly formed Parco Nazionale Tosco Emiliano reveals enchanting trails and diverse ecosystems, inviting you to discover unexpected natural wonders within Tuscany's pristine environment.

Delve deep into the awe-inspiring Orrido di Botri gorge, a dramatic natural feature referenced by Dante himself, offering a unique blend of natural beauty and historical intrigue.

The tranquil Garfagnana Valley, tucked between the Apuan Alps and the expansive Apennines, provides an unparalleled setting for hiking, away from the usual tourist crowds, where medieval hamlets and castles enrich the landscape with cultural heritage.

Experience UNESCO Treasures and Unique Adventures

Journey to Cinque Terre, a UNESCO World Heritage Site, where the picturesque coastal trails and idyllic villages offer a unique and breathtaking hiking destination accessible by foot or a scenic coastal sail.

For an adventurous day trip, visit the walled medieval city of Lucca, rich in history and charm, reachable by a scenic railway, perfectly complementing a hike with cultural exploration.

For a subterranean thrill, explore the Grotta del Vento, one of Europe’s finest limestone cave systems, showcasing Tuscany’s hidden underground marvels.

Throughout your hiking journey in Tuscany, each trail promises awe-inspiring views, an immersive connection with nature, and a chance to experience the region's sublime blend of natural, cultural, and historical riches.

Explore our hiking holidays in Tuscany

Guided Tours of Tuscany: Uncover Hidden Treasures with a Local Expert

Guided Tours: Unlock Tuscany's Secrets with a Local Guide

Imagine treading the sun-dappled paths of Tuscany alongside someone who knows its landscapes like the back of their hand.

That’s the magic of a guided tour.

With a seasoned local expert by your side, each step becomes more than just a journey. 

  • Deeper Insight: A local guide offers a perspective that goes beyond the guidebooks. Discover the secret gems off the beaten path and delve into the tales that give life to these enchanting locales. Their storytelling transforms your hike into a captivating narrative of Tuscany's rich heritage.

  • Seamless Navigation: Tuscany's most breathtaking vistas often lie beyond winding and complex trails. Guided tours guarantee peace of mind as your local guide expertly leads the way through Tuscany’s intricate terrains, ensuring you enjoy every majestic view and cultural highlight without getting lost.

  • Cultural Connection: Immerse yourself in the authentic essence of Tuscany. Your guide introduces you to the local lifestyle, recommends must-try delicacies such as Florentine steak or locally produced wine, and shares intriguing anecdotes that breathe life into Tuscany’s vibrant culture. It’s an intimate glimpse into the Tuscan way of life that enriches your adventure.

By opting for a guided tour, you are not just exploring Tuscany—you are experiencing it through the eyes of a local, gaining a profound understanding and appreciation of this magnificent region.

Explore our guided Tuscany walking and hiking holidays

Self-Guided Walking Tours of Tuscany: Explore at Your Own Pace

Self-Guided Tours: Experience the Freedom of Tuscany

If the idea of leisurely wandering through Tuscany, pausing to enjoy the tranquillity and beauty at your own rhythm, sounds appealing, then a self-guided tour is your ideal journey.

These tours offer the autonomy of exploration with the reassurance of a well-curated itinerary.

  • Flexibility: Set your own pace and tailor your experience. Whether you want to linger in a quaint Tuscan village, savour a leisurely lunch overlooking the rolling hills, or capture the perfect sunset photo, the choice is yours, free from the constraints of a group schedule.

  • Personal Discovery: Forge your own path and let your interests guide you. Venture into Tuscany’s historic towns, explore charming countryside routes, and dive into your personal curiosities without the pressure of a hurried agenda.

  • Comprehensive Resources: While you explore independently, you're not left in the dark. Self-guided tours come equipped with detailed maps, thoughtfully designed itineraries, and rich insights into Tuscany’s cultural and historical landmarks, ensuring your journey is both enlightening and straightforward.

Discover Our Self-Guided Tuscany Walking Holidays

Ways to explore Tuscany

Group walking towards sun in Altai mountains, Siberia on a walking holiday
Classic

Classic Collection walks in Tuscany

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Cave in Matera with view of city at dusk and orange light glow, Italy
Adagio

Adagio Collection walks in Tuscany

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Solo traveller sitting taking in view of Cochamo Valley, Chile on a walking holiday
Self-Guided

Self-Guided Collection walks in Tuscany

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