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Cycling holidays in Tuscany

On Headwater's 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.

Tuscany offers you a great choice for a chcling holiday. You can sample the best of the countryside and classic cities on our hotel-to-hotel 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 cycling holidays in Tuscany, one of our experienced team will be able to help.

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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

Book Early and Save 10%. T&Cs Apply
  • Holiday codeC07ST
  • Holiday typeSelf-guided cycling
  • Duration7 nights, single centre
  • Activity level
  • Excellent for
  • From £1159per person, tour only

  • 29 Reviews
  • All accommodation
  • All breakfasts and 4-course evening meals
  • Bike hire included
  • Headwater navigation provided
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

Book Early and Save 10%. T&Cs Apply
  • Holiday codeC07PF
  • Holiday typeSelf-guided cycling
  • Duration7 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From £1029per person, tour only

  • 8 Reviews
  • All accommodation
  • All breakfasts
  • Bike hire included
  • Navigation app provided
  • Luggage transfers between hotels
Cycling the hills of San Gimignano by E-bike
Italy: Tuscany

Cycling the hills of San Gimignano by E-bike

Cycle through the heart of the San Gimignano region and its stunning surroundings. Ride through cypress dotted rolling hills, meander through valleys adorned with sunflower and poppy fields and explore Tuscany’s hilltop towns.

DEPARTURE MONTHS

JFMAMJJASOND

Book Early and Save 10%. T&Cs Apply
  • Holiday codeC07TY
  • Holiday typeSelf-guided cycling
  • Duration7 nights, single centre
  • Activity level
  • Excellent for
  • From £1299per person, tour only
  • NEW FOR 2025  
  • All accommodation
  • All Breakfasts and 7 dinners
  • Bike hire included
  • Headwater navigation provided