Adventure Holidays in Tuscany

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.

Highlights of Tuscany?

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:

Chianti

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.

Volterra to San Gimignano

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.

Chianciano Terme

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.