Classic Chianti Cycling

Expert Local Guides

Award Winning Adventures

Nature First Adventures

Support Local Communities

11 Days from

USD 3,579

incl. Taxes

Cycling

Ways to Travel :

Self-Guided Holidays

Activity :

Cycling

Activity Levels :

2 out of 7 - Leisurely / Moderate

Ages :

18+

Trip Code :

C10TY

This ten night holiday has been carefully crafted to cleverly balance cultural highlights and historic treasures with natural beauty and stunningly scenic cycling.

It's a perfect choice too if you like the idea of combining timeless countryside cycling with the use of local transport to explore the eternal cities of Siena and Florence on foot.

Your holiday starts in Volterra, a real Etruscan gem with its tangle of alleys home to alabaster workshops and secret chapels, in the heart of the Era Valley. You'll pedal through the archetypal Tuscan countryside, cypress dotted rolling hills, olives, vines, sunflowers, and on, via postcard-pretty Certaldo, to Colle di Val d'Elsa where you'll spend four nights. From here, you can enjoy day trips to the great art cities of Florence and Siena before pedaling on through panoramic wine country to the tiny hamlet of Pescille, a short cycle from medieval San Gimignano. Your route then takes you through the Castelvecchio Nature Reserve (great for bird spotting) giving you a real sense of achievement as you loop back to Volterra for your final night.

Highlights

Quintessential, Italian landscapes: rolling hills, endless vines, beautifully preserved honey-hued hamlets
Mostly 4-star hotels; gorgeous swimming pools; superb local cuisine
Scenic cycling through olive groves, fruit orchards and sunflowers
Spend 4 nights in Colle di Val d'Elsa: charming piazze, Sienese frescoes, easy access to Florence and Siena
Etruscan, Roman, Renaissance and Mediaeval art and architecture

Key Information

10 Nights, hotel-to-hotel accommodation
E-bike hire available on request (supplement applies)
Management by your local Headwater-appointed agent

Countries visited: Italy

What's Included

All buffet breakfasts and 6 evening meals
Route notes and maps
High Quality Bikes
Luggage transfers between hotels

What's Not Included

Travel insurance
Single accommodation (available on request - compulsory supplement)
Solo traveller supplement (where only one person is travelling on a departure date)
Visas or vaccinations

4 Days of Cycling

Terrain:

Lots of the cycling is on off road strada bianca, although at times it has been necessary to use busier roads for short stretches where no alternative exists. Most of the countryside is moderately hilly, so there is every excuse to stop for a breather to admire the view!

Day 2

36 km / 22.4 miles

Day 4

28 km / 17.4 miles

Day 8

40 km / 24.9 miles

Day 10

38 km / 23.6 miles

Responsible Travel

At Exodus we believe in the power of Responsible Travel.

Every time we travel, we are part of a global movement that creates jobs, builds more sustainable societies, encourages cultural understanding and safeguards common natural and cultural heritage. To learn more about what Responsible Travel means to Exodus click here…

Itinerary

Arrive in Volterra where you've time for a dip in the hotel pool and a wander round the town's tangle of cobbled alleys and hidden squares before dinner.
You stay at Hotel San Lino (breakfast and evening meal)

Meals Included: Dinner

Today it's a downhill whizz out of hilltop Volterra and into the pretty Era Valley where spectacular views of the surrounding timeless Tuscan countryside open up as you pedal. After climbing out of the valley, you'll soon pass through the pretty hamlet of Castagno where we suggest a well-deserved coffee stop in the local bar. Your route continues on to Gambassi Terme, a well-preserved spa town with cobbled streets, 12th century church and lovely shaded gardens. Lunch here perhaps in one of the many trattorie then, soon after leaving the town, you'll pick up the famous Via Francigena for the gentle, mainly downhill stretch to medieval Certaldo.
You stay at Hotel Certaldo (breakfast included)

Meals Included: Breakfast

Explore stunning Certaldo, Boccaccio's birthplace. Split into two distinct halves, the medieval centre of Certaldo Alto with its fabulous ancient buildings, is accessed by funicular and offers spectacular views across the Val d'Elsa. On the other hand, Certaldo Basso is the more modern part of the town with shops, bars and restaurants. You could also spend time today, relaxing by the hotel pool.
You stay at Hotel Certaldo (breakfast included)

Meals Included: Breakfast

Today's route explores the panoramic wine country between Certaldo and Colle di Val d'Elsa. You'll follow the official, mainly off-road, Chianti Wine Route where you'll find lots of tasting opportunities! It's then on to the old town of Poggibonsi, a perfect stop for lunch and to visit the ruins of its unfinished 15th century fortress. The day ends with gentle pedalling through tree-lined meadows and a valley of poppy and sunflower fields to Colle di Val d'Elsa.
You stay at Palazzo San Lorenzo (breakfast and evening meal)