Your Cycling Holidays in Italy

Tuscany & the Chianti Hills E-Bike Safari

From the cypress-lined paths of Gladiator to the beautiful villa featured in Kenneth Branagh’s Much Ado About Nothing, this dreamy Tuscan tour seems to take you from one beautiful film set to another. 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 equipped with.

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

  • Hotel accommodation 
  • All breakfasts, 6 lunches and dinners plus refreshments (on guided tours)
  • Bed & breakfast on self-guided tours
  • Luggage transfers
  • Raleigh e-bikes with personalised fittings
  • Helmets provided
  • Bikes, panniers and puncture repair kits
  • Route maps and instructions (GPS on request)
  • Assistance from our rep whenever needed
  • All private tours, events and entrance fees (on guided tours)

This tour is operated by our preferred local partner

Your Cycling Holidays in Italy

Tuscany & the Chianti Hills E-Bike Safari

7 Day E-Cycle Tour

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. There will be time today to wander its medieval streets before returning to your hotel, where you’ll be fitted out with your e-bike.

Day 2

Cortona to San Quirico: 3hr20 cycle time. Today we begin our adventure across Tuscany, cycling across the plain of the Val di Chiana towards the rolling Tuscan hills. We stop mid morning at a local cafe for the first of our five coffee stops along the way. Entering the renowned wine area of Montepulciano, here you can sample a few delicious local tipples over lunch. We then continue towards San Quirico, where we’ll stay the night, through spectacular scenery that typifies everything you’ve always envisaged Tuscany to be.

Day 3

Val d’Orcia and back: 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 to save his family and after, make our second stop to indulge in un caffé. Next we enter the Montalcino wine area, passing Castelnuovo dell’Abate and the famous Abbey of Sant’Antimo. Stopping here for lunch and to taste more lovely wine, you can also visit the bike museum before returning to San Quirico d’Orcia via the town of Montalcino.

Day 4

San Quirico to Asciano: 2hr20 cycle time. A gentle cycle day across classic Tuscan terrain with dramatic panoramas in every direction, the route takes us through the medieval village of Asciano where you can enjoy another delightful coffee stop and a wood-fired oven pizza for lunch. You will also, once again, indulge in gorgeous local Tuscan wines. The beautiful city of Siena is 10km away, for those keen to venture a little further to explore it. The overnight stay is 10k from Siena and the famous ‘Crete Senesi’.

Day 5

Asciano to Radda: 32 miles (51km: 2hr40 cycle time). 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. 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: 3hr50 cycle time. 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 Holidays in Italy

Tuscany & the Chianti Hills E-Bike Safari

Accommodation Options

A fine selection of options to choose from

  • Castello di Leonina Relais

    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



    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

    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

    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 Holidays in Italy

Tuscany & the Chianti Hills E-Bike Safari

2018 Departure Dates & Prices

2018 Departure Dates Nights   Occupancy   Basis   Adult Price 
May, June, September, October 7 2 Sharing Guided & Full Board £2895
May to October 7 2 Sharing Self-Guided & Bed & Breakfast £1525
May to October  5 2 Sharing Self-Guided & Bed & Breakfast £1195

Half Board Supplement (7 Nights): £245 per person

Half Board Supplement (5 Nights): £175 per person


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