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Your Cycling Holidays in Tuscany & Umbria

Tuscany & The Chianti Hills | Self Guided

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

Starting high in the Tuscan hills, in the pretty town of Cortona, this tour takes you deep into the most enticing Chianti wine territory - with  tasting sessions on six out of seven days and mid morning breaks to sample Italy's second best export, its coffee.

The views from the top of the Chianti hills are spectacular - and far easier to enjoy, thanks to the Raleigh e-bike you’ll be equipped with.

What's included

  • Six delicious lunches and dinners

  • Premium bed and breakfast accommodation

  • Expert on the spot support

  • Luggage transferred between your hotels

  • Fully serviced electric bikes

  • 100% financial security through ABTA and ATOL

Your Cycling Holidays in Tuscany & Umbria

Tuscany & The Chianti Hills | Self Guided


DAY 1 | Arrive at Perugia, Florence or Rome airport and transfer to Cortona 
This lovely hillside town is a natural balcony for the Val di Chiana with stunning views towards Lake Trasimeno, 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 and briefed on how to use it before enjoying your first wine tasting of the holiday.

DAY 2 | Cortona to San Quirico | Cycle time 3 hours 20 minutes  
Today you'll begin your adventure across Tuscany, cycling across the plain of the Val di Chiana towards the rolling Tuscan hills. Stop mid morning for a break and a gorgeous espresso then enter the renowned wine area of Montepulciano. Here, you can sample a few more delicious tipples over lunch. You'll then continue towards San Quirico, where you will stay the night, through spectacular scenery that typifies everything you’ve always envisaged Tuscany to be.

DAY 3 | Val d’Orcia and back | Cycle time 3 hours 30 minutes
Today you take a round trip through Pienza, dropping into the Val d’Orcia with the pointed peak of Monte Amiata as your backdrop. You will cycle through the same fields that ‘Gladiator’ Maximus is seen galloping home to save his family after, make our second stop to indulge in un caffé. Next you enter the Montalcino wine area, passing Castelnuovo dell’Abate and the famous Abbey of Sant’Antimo. Stopping here for lunch and 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 | Cycle time 2 hours 20 minutes
A gentle cycle day across classic Tuscan terrain with dramatic panoramas in every direction, the route takes you through the medieval village of Asciano where you can enjoy another delightful coffee stop and then 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 10km from Siena and the famous ‘Crete Senesi’.

DAY 5 | Asciano to Radda | Cycle time 2 hours 40 minutes
Following the tracks of the vintage cycle race, today you 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 you'll 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 | Cycle time 3 hours 50 minutes 
After a night in Radda, you’ll enjoy a blissful descent back to the foot of Cortona, across the valley of the Chiana, stopping for our last mid morning coffee of the trip, then our last wine sampling session in the afternoon. 

After your final long, lazy breakfast in the Tuscan hills, we say “Arrivederci”.

What not to miss:

  • The Monastery of Sant’Anna in Camprena where The English Patient was filmed.

  • Bagno Vignoni, where you can plunge your feet into deliciously warm spa waters.

  • ‘Crete Senesi’, or Siennese Clay.

This tour is operated by our preferred local partner.

Your Cycling Holidays in Tuscany & Umbria

Tuscany & The Chianti Hills | Self Guided

  • Castello di Leonina Relais

    4 star

    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 hydro massage area.

  • Hotel Villa del Capitano

    4 star

    A modern designer hotel set in a historic reinassance 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.

  • Hotel Villa Marsili

    4 star

    Famed for its spectacular breakfasts, the hotel Villa Marselli 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.  

  • Livernano

    4 star

    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.

Your Cycling Holidays in Tuscany & Umbria

Tuscany & The Chianti Hills | Self Guided

Tour Only Prices | 2019

2019 Departure Dates Nights Board Basis Adult Price
April to October 7 Bed & Breakfast £1545
April to October 5 Bed & Breakfast £1215
April to October 7 Half Board  £1845
April to October 5 Half Board  £1435

Full Board Prices | 2019

2019 Departure Dates Nights Board Basis Adult Price
On Request 7 Full Board £2895

Single Occupancy (7 Nights): £60 per night

Single Occupancy (5 Nights): £66 per night

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