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Holidays in Tuscany

On Headwater's activity 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 cycling holiday or walking, 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.

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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 US$2349per person, tour only

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

A Taste of Tuscany Cycling

This single-centre cycling holiday introduces you to quintessential Tuscany; it 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 US$2499per person, tour only

  • 13 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 US$2849per person, tour only

  • 48 Reviews
  • All accommodation
  • All continental breakfasts and 6 evening meals
  • Bike hire included
  • Headwater navigation 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 Call usper person, tour only
  • NEW FOR 2023  
  • All accommodation
  • All breakfasts and 2 evening meals
  • Route notes 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, and there are the opportunities to lengthen the rides, or take the train at some stages to spend extra time at your destinations.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday codeC07PF
  • Holiday typeSelf-guided cycling
  • Duration7 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From US$1879per person, tour only
  • NEW FOR 2023  
  • All accommodation
  • All breakfasts
  • Bike hire included
  • 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 US$2399per person, tour only

  • 55 Reviews
  • All accommodation
  • All continental breakfasts and 4 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 US$2679per person, tour only

  • 30 Reviews
  • All accommodation
  • All continental breakfast and 4 evening meals
  • Route notes provided
  • Luggage transfers between hotels
  • Flights from London (if booking incl. flights)
Classic Chianti Cycling
Italy: Tuscany

Classic Chianti Cycling

This 10-night cycling tour 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 with views that extend as far as Corsica on a clear day!

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday codeC10TY
  • Holiday typeSelf-guided cycling
  • Duration10 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From US$3179per person, tour only

  • 26 Reviews
  • All accommodation
  • All buffet breakfasts and 6 evening meals
  • Bike hire included
  • Headwater navigation provided
  • Luggage transfers between hotels
  • Flights from London (if booking incl. flights)