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
Navigation App
15% OFF THIS TRIP
VIEW TRIP
Self-guided cycling
7 nights,
single centre
Level: 2+
Moderate plus
Headwater
Navigation App
15% OFF THIS TRIP
VIEW TRIP
Self-guided walking
7 nights,
twin centre
Level: 2+
Moderate plus
Headwater
Navigation App
15% OFF THIS TRIP
VIEW TRIP
Self-guided walking
7 nights,
hotel-to-hotel
Level: 2
Moderate
Headwater
Navigation App
10% OFF THIS TRIP
VIEW TRIP
Tap here to filter results
Filter and sort
Holiday type
All
Destination
All
Departure month
All
Activity level
All
Accommodation type
All
Best for
All
Sorted by
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.
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.
