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.
The Tuscan scenery is timeless and breath-taking and you'll be spoilt for choice when choosing an area to explore. We've listed a handful of destinations which are ideal for a walking or cycling holiday in Tuscany:
Explore the beautiful wine region of Chianti, where you'll find rolling hills and endless vineyards. Immerse yourself in the quintessential Tuscan culture and learn about the area's history, art, cuisine, and, of course, wine! You'll also get the chance to visit the World Heritage cities of Florence and Siena.
Walk amongst the timeless countryside between Volterra and San Gimignano and spot sleepy hilltop hamlets and sunflower fields. This scenic walking route offers the chance to taste the local cuisine, from fresh ribbons of pasta to toasted bruschetta soaked in olive oil. Don't worry - there are wine-tasting opportunities thanks to the array of vines that surround San Gimignano, the small city known as the medieval 'Manhattan of Tuscany', thanks to its soaring towers.
Get a true taste of Tuscany and start in Chianciano Terme, where you'll walk over the hills around La Pietriccia. Admire the stunning views of Monte Marzolana and take in the glorious Tuscan surroundings. You'll meet local produce providers and can bathe in sulphur-rich healing waters. Make sure you don't miss the wine and cheese towns of Montepulciano and Pienza.
Self-guided walking
7 nights,
single centre
Activity level: 4
Half board
Self-guided cycling
7 nights,
single centre
Activity level: 4
Half board
Self-guided walking
7 nights,
twin centre
Activity level: 4
Bed and
breakfast
Self-guided cycling
7 nights,
hotel-to-hotel
Activity level: 4
Bed and
breakfast
Self-guided walking
7 nights,
hotel-to-hotel
Activity level: 4
Breakfasts plus
1 meal
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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.rating of 4.6 on Feefo. - 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.British Travel Awards, having received prizes for Best Travel Company to Central/Western Europe and Best Company for UK Breaks Holidays.People, Places & Planet plan.read all about your rights when booking a tour with us.
