Walking & Cycling 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.

Read more▼


A Taste of Tuscany Walking
Italy: Tuscany

A Taste of Tuscany Walking

Based in the town of Chianciano Terme, on this single-centre walking holiday you’ll experience archetypal Tuscany: stunning timeless landscapes, delicious rustic cuisine, friendly local people and, of course, interesting walking routes.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday codeW07ST
  • Holiday typeSelf-guided walking
  • Duration7 nights, single centre
  • Activity level
  • Excellent for
  • From £1649per person, tour only

  • 27 Reviews
  • All accommodation
  • All breakfasts and 4-course evening meals
  • Headwater navigation provided
  • Flights from London (if booking incl. flights)
A Taste of Tuscany Cycling
Italy: Tuscany

A Taste of Tuscany Cycling

Introducing you to quintessential Tuscany, this cycling holiday has all the ingredients to create a wonderful lasting impression of this rightly famous region. The landscapes, the food, the people and, of course, perfect cycling routes. This is not just a cycling holiday it is an immersion into local Tuscan life.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday codeC07ST
  • Holiday typeSelf-guided cycling
  • Duration7 nights, single centre
  • Activity level
  • Excellent for
  • From £1699per person, tour only

  • 28 Reviews
  • All accommodation
  • All breakfasts and 4-course evening meals
  • Bike hire included
  • Headwater navigation provided
  • Flights from London (if booking incl. flights)
Secrets of San Gimignano Cycling
Italy: Tuscany

Secrets of San Gimignano Cycling

This 8-night cycling holiday combines fabulously unspoilt Chianti countryside with the chance to visit the world-famous cities of Florence and Siena. You'll stay in high quality hotels, enjoy superb meals and relax by panoramic pools - views extend as far as Corsica on a clear day!

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday codeC08TY
  • Holiday typeSelf-guided cycling
  • Duration8 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From £2019per person, tour only

  • 57 Reviews
  • All accommodation
  • All continental breakfasts and 4 evening meals
  • Bike hire included
  • Headwater navigation provided
  • Luggage transfers between hotels
  • Flights from London (if booking incl. flights)
Cycling in Tuscany: Pisa to Florence
Italy: Tuscany

Cycling in Tuscany: Pisa to Florence

Cycle from the iconic leaning tower of Pisa to the Ponte Vecchio in Florence, passing through beautiful Tuscan landscape that inspired artists and composers such as Leonardo da Vinci and Puccini. The gentle cycling is mainly along riverside paths and quiet roads.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday codeC07PF
  • Holiday typeSelf-guided cycling
  • Duration7 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From £1289per person, tour only

  • 5 Reviews
  • All accommodation
  • All breakfasts
  • Bike hire included
  • Navigation app provided
  • Luggage transfers between hotels
  • Flights from London (if booking incl. flights)
Wine & Walk in Chianti
Italy: Tuscany

Wine & Walk in Chianti

Walk through the beautiful wine-growing area of Classic Chianti, visiting the World Heritage cities of Florence and Siena.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday codeW07TU
  • Holiday typeSelf-guided walking
  • Duration7 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From £1299per person, tour only

  • 1 Reviews
  • All accommodation
  • All breakfasts and 1 evening meal
  • Route notes provided
  • Luggage transfers between hotels
  • Flights from London (if booking incl. flights)
Volterra to San Gimignano Walk
Italy: Tuscany

Volterra to San Gimignano Walk

This 8-night walking holiday combines fabulously unspoilt Chianti countryside with the chance to visit the world-famous cities of Florence and Siena. You'll stay in a mix of friendly, family-run hotels, enjoy superb meals and relax by panoramic pools - views extend as far as Corsica on a clear day!

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday codeW08TY
  • Holiday typeSelf-guided walking
  • Duration8 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From £1699per person, tour only

  • 64 Reviews
  • All accommodation
  • All continental breakfasts and 2 evening meals
  • Route notes provided
  • Luggage transfers between hotels
  • Flights from London (if booking incl. flights)
Chianti Classic Walk
Italy: Tuscany

Chianti Classic Walk

A 10-night walking holiday that explores the fabulously unspoilt Chianti countryside, with the chance to visit the world-famous cities of Florence and Siena too! Stay in friendly, family-run hotels, including a beautifully restored 12th century abbey, and enjoy superb meals.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday codeW10TY
  • Holiday typeSelf-guided walking
  • Duration10 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From £1899per person, tour only

  • 33 Reviews
  • All accommodation
  • All continental breakfast and 2 evening meals
  • Route notes provided
  • Luggage transfers between hotels
  • Flights from London (if booking incl. flights)

Frequently asked questions

Is Tuscany good for walking?

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.

What time of year is best for walking in Tuscany?

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.

How many days in Tuscany is enough?

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.

What is the most scenic route in Tuscany?

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.

What can I expect from your walking holiday in Tuscany?

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:

  • Hotel accommodation included and pre-booked by us
  • Routes, maps, and detailed notes
  • GPS route directions
  • Dedicated luggage moving, so you won't have to carry around your heavy bags
  • Optional flights and airport transfers

What should I pack for a walking holiday in Tuscany?

Besides your typical walking clothes, boots, and sunglasses, we also recommend you pack:

  • Sun hat/cap
  • High SPF sun protection
  • Light jacket
  • Water bottles and/or hydration systems
  • Small backpack for carrying essentials
  • Basic first aid kit, including any medication you might need
  • Plenty of snacks
  • Wallet with foreign currency cash
  • Compass, notepad, and pencil

Why choose Headwater for walking & cycling holidays in Tuscany?

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.

LEARN MORE ABOUT HEADWATER