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Holidays in Chianti

Inhabited since ancient times by the Etruscans, the area was also controlled by the Romans prior to mediaeval times and all have left their mark over the centuries. Scenic Etruscan trails, pilgrims' paths and pretty mediaeval hilltop hamlets are scattered among the quintessential Italian landscape of sunflowers, vines and cypress trees - it's easy to see why the area has so inspired artists and writers for centuries. You'll feel as though you're passing through history as you effortlessly discover sleepy hilltop hamlets crowning sun-dappled hills, verdant vineyards and panoramic picnic spots in fields ablaze with sunflowers.

This is a side of Italy that few visitors ever see - farmers harvesting olives, infinite views over the rolling plains, lively fetes in hidden hilltop villages - and to appreciate it fully you need to slow right down. We have both walking and cycling holidays here which offer the perfect opportunity to soak up the atmosphere of this beautiful region.

Occupying the north/south axis from Florence down to Siena, the Chianti region is famous the world over for its fine wines and exceptional food, but there's more than just food and wine as you will discover on our walking and cycling holidays.

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View 4 holidays below


Volterra to San Gimignano Walk

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 £1179per person, tour only

  • 42 Reviews
  • All continental breakfasts and six evening meals
  • Route notes and maps provided
  • Luggage transfers between hotels
Secrets of San Gimignano Cycling

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

  • 35 Reviews
  • All continental breakfasts and 6 evening meals included
  • High quality bikes provided
  • Route notes and maps provided
  • Luggage transfers between hotels
Chianti Classic Walk

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 £1339per person, tour only

  • 24 Reviews
  • Continental breakfast and 6 evening meals
  • Route notes and maps provided
  • Luggage transfers between hotels
Classic Chianti Cycling

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 £1579per person, tour only

  • 21 Reviews
  • All buffet breakfasts and 6 evening meals included
  • High quality bikes provided
  • Route notes and maps provided
  • Luggage transfers between hotels