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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.

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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 typeSelf-guided walking
  • Duration7 nights, single centre
  • Activity level
  • Excellent for
  • From £999per person, tour only
  • All buffet breakfasts and 4-course evening meals
  • Route notes and maps provided
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 typeSelf-guided cycling
  • Duration7 nights, single centre
  • Activity level
  • Excellent for
  • From £1049per person, tour only
  • All buffet breakfasts and 4-course evening meals
  • High quality bikes provided
  • GPS route navigation provided
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 typeSelf-guided walking
  • Duration8 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From £1159per person, tour only

  • 40 Reviews
  • All continental breakfasts and 6 evening meals
  • Route notes and maps provided
  • Luggage transfers between hotels
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 typeSelf-guided cycling
  • Duration8 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From £1299per person, tour only

  • 38 Reviews
  • All continental breakfasts and evening meals
  • High quality bikes provided
  • GPS route navigation provided
  • Luggage transfers between hotels
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 C12 abbey, and enjoy superb meals.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday typeSelf-guided walking
  • Duration10 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From £1319per person, tour only

  • 23 Reviews
  • All continental breakfast and 6 evening meals
  • Route notes and maps provided
  • Luggage transfers between hotels
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 typeSelf-guided cycling
  • Duration10 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From £1549per person, tour only

  • 22 Reviews
  • All buffet breakfasts and 8 evening meals
  • High quality bikes provided
  • GPS route navigation provided
  • Luggage transfers between hotels