Holidays in Chianti

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.

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.

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Volterra to San Gimignano Walk

Poppy field with San Ginignano town

From $1825 per person

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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!

Departures:
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  • 8 nights, hotel-to-hotel
  • All continental breakfasts and six evening meals
  • Holidays with gastronomic meals.
  • Holidays with wine-tasting opportunities.
  • Varied routes for nature lovers and botanists.
  • Discover stunning historic sites en-route.
  • Lots of swimming opportunities.
  • Perfect for couples.

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Secrets of San Gimignano Cycling

Poppy field with San Ginignano town

From $2015 per person

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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!

Departures:
J
F
M
A
M
J
J
A
S
O
N
D
  • 8 nights, hotel-to-hotel
  • All continental breakfasts and 6 evening meals included
  • Holidays with gastronomic meals.
  • Holidays with wine-tasting opportunities.
  • Varied routes for nature lovers and botanists.
  • Discover stunning historic sites en-route.
  • Lots of swimming opportunities.
  • Eco-friendly holidays.
  • Perfect for couples.

View holiday

Chianti Classic Walk

San Gimignano from countryside.

From $2075 per person

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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.

Departures:
J
F
M
A
M
J
J
A
S
O
N
D
  • 10 nights, hotel-to-hotel
  • Continental breakfast and 6 evening meals
  • Holidays with gastronomic meals.
  • Holidays with wine-tasting opportunities.
  • Varied routes for nature lovers and botanists.
  • Discover stunning historic sites en-route.
  • Lots of swimming opportunities.
  • Perfect for couples.

View holiday

Classic Chianti Cycling

San Gimignano city  from Tuscan countryside.

From $2445 per person

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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!

Departures:
J
F
M
A
M
J
J
A
S
O
N
D
  • 10 nights, hotel-to-hotel
  • All buffet breakfasts and 6 evening meals included
  • Holidays with gastronomic meals.
  • Holidays with wine-tasting opportunities.
  • Varied routes for nature lovers and botanists.
  • Discover stunning historic sites en-route.
  • Lots of swimming opportunities.
  • Eco-friendly holidays.
  • Holidays to enhance your wellbeing.
  • Perfect for couples.

View holiday

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Email: info@breakaway-adventures.com

Open 9:00-5:30 Mon-Fri, 9:00-12:00 Sat.

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Headwater's Holidays in Chianti 4.7008547008547 117
  • ATOL Protected (No. 9957)
  • IATA Registered
  • ABTA Member (No. W1593)
  • Relaxed activity holidays since 1985

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call us: 1-800-567-6286 or email: info@breakaway-adventures.com

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