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01707 817260
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Call us on 01707 817260

  • Monday - Friday9am - 5pm
  • Saturday9am - 1pm
  • SundayClosed
  • Bank HolidaysClosed

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Walking Grade: Gentle - Challenging

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Single Rooms

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Walking 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 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.

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Popular walking holidays in Tuscany

Adagio
Tuscany's Treasures

Tuscany's Treasures
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Departure dates

  • 2025:
    • Jun
    • 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!

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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.  

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

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

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

  • 2025: Apr - 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.

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

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

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

  • 2025: Apr - 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.

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

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Pilgrimage Routes
From £859
7 Nights
Tour only
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Why choose Ramble Worldwide

Here at Ramble Worldwide, we are the experts in walking in Tuscany. Explore the culture through food and wine, or the arts and history. There's so much to take in by foot whether that is self-guided or guided tours.

Whether you are in a group or solo, all travellers are welcome on our guided tours of Tuscany. Each group has a tour leader who will guide you through your Italian journey. Explore Tuscany with our self-guided tours. Choose from walking tours that visit Florence, Siena, or Lucca for a unique experience.

“The holiday provided an opportunity for some challenging but enjoyable walking in a lovely, unspoilt area of Italy.” (Verified FEEFO customer review)

Whatever you want to experience, explore our walking tours in Tuscany, and book with Ramble Worldwide today.

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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Frequently asked questions about Tuscany walking holidays

  • Is Tuscany good for walking?

    Tuscany is a perfect destination for an Italian walking holiday. This place is great for all kinds of adventures. It has beautiful countryside views and historical old towns and villages. View all our Tuscany walking holidays and book today.

  • Where is the most beautiful part of Tuscany?

    Tuscany is an incredible and breathtaking destination - a must for all travellers. To capture the full Tuscan experience, we recommend visiting Florence and Siena. Enjoy the art and history and the amazing food and wine.

  • When is the best time of the year to visit Tuscany?

    Tuscany is beautiful all year round and there are a variety of activities to enjoy regardless of the weather. The best time of the year to go on a walking holiday to Tuscany is between April and October.

  • What is Tuscany famous for?

    Tuscany is famous for its breathtaking landscapes of hills and mountains, as well as the stunning views of vineyards and mediaeval towns. This location is appropriate for all types of travellers.

  • Is there any walking holiday in Tuscany for singles?

    At Ramble Worldwide, we offer self-guided or guided group tours that are perfect for solo travellers. You can travel around with a group including a local guide, who will lead you through your Italian journey from start to finish. The guided tours include free days to go and explore on your own.

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