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Your cycling holiday in Cycling Holidays Italy

Tuscany & the Chianti Hills E-Bike Safari | Guided Group

Following in the tracks of your expert local e-bike Leader, all you have to consider is the last and the next glass of wine, wonder what sights may unfold over the next brow and what's for dinner!

As 92% of Tuscany’s terrain is either hills or mountain, the views are spectacular - and far easier to enjoy, thanks to the Raleigh e-bike you'll be riding.

What not to miss

  • Tasting wine along the enticing Chianti wine territory
  • Visiting the famous Abbey of Sant'antimo
  • Taking in the stunning views of Lake Trasimeno from Cortona
  • Indulging in un caffé - the Italian way, with our mid morning coffee stops at traditional cafes
  • Tasting the many tipples of local vino with wine tasting sessions on six of the seven days you are in Tuscany

What's included

  • Expert local leader and tour guide
  • ​​Premium hotel accommodation
  • All breakfasts, 6 lunches and dinners plus refreshments
  • All private tours, events and entrance fees
  • Luggage transfers
  • Raleigh e-bikes with personalised fittings
  • Helmets and very good quality rain capes
  • Bikes, panniers and puncture repair kits

Group size maximum : 8 per group plus local leader.

This tour is operated by our preferred local partner.

Your cycling holiday in Cycling Holidays Italy

Tuscany & the Chianti Hills E-Bike Safari | Guided Group

Day 1

Arrive at Perugia, Florence or Rome and transfer to Cortona 

This lovely hillside town is a natural balcony for the Val di Chiana with stunning views towards LakeTrasimeno, Montepulciano and the Tuscany hills. Your week begins with a private wine lesson and orientation from Marco Molesini! This will be followed by your first delicious dinner. You’ll also be fitted out with your e-bike.

Day 2

Cortona to San Quirico | Cycle time 3 hours 20 minutes 

Today we begin our adventure across Tuscany, cycling across the plain of the Val di Chiana towards the rolling Tuscan hills. Entering the renowned wine area of Montepulciano, you can sample a few delicious local tipples over a wonderful lunch. Our afternoon ride visits Sant'Anna in Camprena, where scenes from The English Patient were filmed. The route to San Quirico through goose-bump inducing, classical Tuscan scenery will stay with you as a life long memory. We then continue towards San Quirico, where we’ll stay the night.

Day 3

Val d’Orcia and back | Cycle time 2 hours 20 minutes 

Today we take a round trip through Pienza, dropping into the Val d’Orcia with the pointed peak of Monte Amiata as your backdrop. We will cycle through the same fields that ‘Gladiator’ Maximus is seen galloping home through to save his family. At the spa village of Bagno Vignoni, grab a coffee as you marvel at the natural waters. Next we pedal in to the Brunnello region to discover a history of modern Italian bike racing, delicious lunch and a taste of the Brunello Super Tuscan wines.

Day 4

San Quirico to Asciano | Cycle time 2 hours 20 minutes

A gentle cycle day across classic Tuscan terrain with dramatic panoramas in every direction. Meet smiling pilgrim walkers along the Via Francigena - the famous pilgrimage route from Canterbury to Rome & Jerusalem. As we pedal towards Asciano you can enjoy another delightful coffee stop and a wood-fired oven pizza for lunch. You will also have the opportunity to indulge in gorgeous local Tuscan wines. The beautiful city of Siena is just 10km away, for any of the group keen to venture a little further.

Day 5

Asciano to Radda | Cycle time 2 hours 40 minutes 

Following the tracks of the L’eroica vintage cycle race, today we head north into the rolling hills of classic ‘Chianti country’ for wine tasting in yet more amazingly beautiful film-set style territory.

Day 6

Chianti | Cycle time 2 hours 50 minutes

Today we explore the best of Chianti: Greve and the surrounding countryside of shallow, wooded valleys; and Radda, a delightful medieval town, where we will stop to sample an espresso mid morning. Along the way, you’ll be able to sample several highly regarded DOCG wines: Chianti, Chianti Classico and Chianti Superiore. Best enjoyed while sitting in a sun-filled piazza over a spot of lunch.

Day 7

Radda to Cortona | Cyclye time 3 hours 50 minutes

It's all down hill today! After a night in Radda, we’ll enjoy a blissful and gradual descent back to the foot of Cortona, across the valley of the Chiana, stopping for our last gorgeous coffee of the trip mid morning, then our last wine sampling session in the afternoon.

Day 8

We say “Arrivederci” before transferring you direct from Cortona to Perugia, Florence or Rome by train or minibus.

Your cycling holiday in Cycling Holidays Italy

Tuscany & the Chianti Hills E-Bike Safari | Guided Group

Your cycling holiday in Cycling Holidays Italy

Tuscany & the Chianti Hills E-Bike Safari | Guided Group

Note: The accommodation listed below is indicative, it is not guaranteed and is subject to availability. Alternative accommodation of an equal standard may be used.

Castello di Leonina Relais


The hotel was originally a 13th-century castle and has beautiful views of the hills surrounding Asciano. The restaurant has a beautiful terrace and there is wellness area including a sauna and an outdoor swimming pool with hydromassage area.



Livernano is both a stunning hotel and a working farm, producing fine wines, excellent olive oil and honey, vegetables and fruits. Developed from rustic brick houses overlooking vineyards and olive groves, this refined boutique hotel has a winery and a spacious outdoor swimming pool.

Villa del Capitano


A modern designer hotel set in a historic renaissance villa, located near the ancient town walls with views of the Val d'Orcia. A mix of artworks line the walls and a hot tub on the roof terrace is the perfect place to unwind. 

Villa Marsili


Famed for its spectacular breakfasts, the hotel Villa Marsili is a real gem in the charming town of Cortona. It’s frescoed walls and antique furniture are quintessentially Tuscan, just like the stunning views of the valley you will see from the garden area.  

Your cycling holiday in Cycling Holidays Italy

Tuscany & the Chianti Hills E-Bike Safari | Guided Group

Guided Group Dates and Prices 2020

2020 Tour Only Dates Nights Adult Price  
4 May – 11 May 7 £2895 Enquire Now
19 May – 26 May 7 £2895 Enquire Now
14 September - 21 September 7 £2895 Enquire Now

These are guide prices, please call one of our experts for a detailed quote.

Group size maximum : 8 per group plus local leader.

Single Occupancy : £60 per night

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