On Headwater's walking & cycling holidays in Tuscany you'll discover beautiful, timeless landscapes, great art cities and truly outstanding cuisine. For many, the great art city of Florence is the most beautiful city in the world. You can hunt for bargains at San Lorenzo market, or cross to the quieter side of the Arno at the Boboli Gardens. Away from the cities, the countryside is home to a wealth of bird and animal life - look out for badgers foraging in the fields, herons and otters by the streams and golden eagles soaring overhead.
Whether you're looking for a walking holiday or cycling, Tuscany offers you a great choice. You can sample the best of the countryside and classic cities on our hotel-to-hotel walking and cycling holidays in Tuscany, and on our single-centre trips you'll experience archetypal Tuscany and home-grown food.
Tuscany is quintessential and timeless Italy, offering a wealth of stunning locations to discover on a walking or cycling holiday. And despite its popularity it remains largely unspoilt. This was the beloved homeland of Galileo, Dante and Machiavelli. And it was here that Michelangelo, Donatello and Leonardo da Vinci lived and worked.
But don't just take our word for how amazing it is - you must see it for yourself. If you're about to plan your next holiday and have any questions about one of our activity holidays in Tuscany, one of our experienced team will be able to help.
Self-guided walking
7 nights,
single centre
Level: 2
Moderate
Headwater
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Self-guided cycling
7 nights,
single centre
Level: 2+
Moderate plus
Headwater
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Self-guided walking
7 nights,
twin centre
Level: 2+
Moderate plus
Headwater
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Self-guided cycling
7 nights,
hotel-to-hotel
Level: 2
Moderate
Navigation App
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Where appropriate, we grade our holidays based on distance, terrain, elevation gain, remoteness, etc and categorise them into 4 relative groups. This is ultimately subjective and may vary slightly day to day; for more advice, please see the specific trip page or call one of our friendly team.
Tuscany is an excellent location if you're looking for a walking holiday. There are plenty of well-established walking trails and routes, offering picturesque, idyllic views along the way.
The region offers some of the best places to walk in Italy, so whether you're a hiking fanatic or are looking for an easy walking holiday, prepare to take in the beautiful sights of Italy at your own pace.
We recommend that you plan your Tuscany walking tour for mid-to-late spring (April to May) or early autumn (September to October). These months offer pleasant weather, vibrant landscapes, and comfortable temperatures.
Whilst the Tuscan countryside is often quiet, the towns can be quite busy during the high season (June to September) and temperatures tend to rise.
Our Tuscany walking holidays range between seven- and 10-night stays. This allows you to explore the region at your own relaxed pace, spending your days sight-seeing or taking part in local activities. Plus, you'll have time to stroll through the countryside and visit the famous cities of Florence and Siena.
Each of our Tuscany walking tours has beautifully scenic routes for you to admire.
The Volterra Loop takes you through lush countryside, where you'll spot the rolling hills and charming villages en route. Walk towards San Gimignano through wineries and olive groves and submerge yourself in authentic Italian culture.
Or, if you're a wine lover, why not explore the Chianti region? The Gaiole area features a signposted network of various hiking trails through the fabled Chianti countryside, where you can take in the incredible castles, farms, and vineyards.
For a real taste of life in the Italian countryside, our walking holidays in Tuscany could be just what you're looking for. Perfect for those who love the great outdoors and enjoy staying active, our walking tours will have you out and about for most of the day.
Our self-guided walking tours come with a full itinerary, allowing you to explore the region at your leisure. You'll have the opportunity to experience the local cuisine, history, and culture, which will make for the perfect Italian adventure.
When you book with Headwater, you can expect an excellent level of service. We want to make your holiday as smooth as possible, with benefits including:
Besides your typical walking clothes, boots, and sunglasses, we also recommend you pack:
With nearly 40 years' experience creating expertly crafted itineraries with hand-picked recommendations, you can rely on us to provide you with an unforgettable walking holiday. Book online with confidence today and prepare to plan your next adventure.
Satisfied customers - We strive to deliver you excellent customer service, which is why we've received a rating of 4.6 on Feefo.
Exciting destinations - We use a five-step approval process to find the best locations to ensure you experience an unforgettable walking tour. We hand-pick the hotels on each route, complete with hosts to look after you during your stay.
We'll arrange your flights - We'll take care of your entire booking process, including the booking of your flights. From taking off to coming home, we want you to have a smooth and seamless holiday.
Award-winning provider - Our adventure tours have been rewarded by the British Travel Awards, having received prizes for Best Travel Company to Central/Western Europe and Best Company for UK Breaks Holidays.
Sustainability at our heart - We're always working towards reducing the impact that our tours have on the environment and are striving to become Nature Net Positive. We're committed to running sustainable tours, which is part of our People, Places & Planet plan.
ABTA- and ATOL-protected - You can rest assured that your Tuscany walking tour is ABTA- and ATOL-protected. Make sure that you read all about your rights when booking a tour with us.
Helping communities - We want to make a difference in disaster relief and social and conservation causes, which is why we set up the Exodus Travels Foundation to give back to communities around the world.
