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Your Cycling Holidays in Tuscany & Umbria

Tuscan Valleys eBike Holiday | 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 Montepulciano and Montalcino wine territory.

The views around Asciano and the Crete Senesi are spectacular - and far easier to enjoy, thanks to the Raleigh e-bike you’ll be equipped with.

What's included

• Number of nights half board or B&B accommodation as specified
• Expert on the spot support
• Luggage transfers between your hotels
• Fully serviced Raleigh Motus electric bikes
• 100% financial security through ABTA and ATO

Please note that this tour is available in two versions, with different levels of accommodation, Classic and Indulgence. With the indulgence package, you may find some minor changes to the suggested itinerary displayed. Speak to our Activities Experts on 020 7471 7760 for more details.

Your Cycling Holidays in Tuscany & Umbria

Tuscan Valleys eBike Holiday | Self Guided

Classic Tour

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. At your hotel you’ll be fitted out with your e-bike and briefed on how to use it before your first taste of Umbrian cuisine.

DAY 2 | Cortona to Montefollocino | Cycle time 2 hours 10 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 Montefollocino, where you will stay the night, through spectacular scenery that typifies everything you’ve always envisaged Tuscany to be.

DAY 3 | Montefollocino to Castello di Leonina | Cycle time 2 hours 30 minutes
Yet more verdant panoramas await today as you venture deeper into Tuscany through rolling vineyards. From Montefollocino, you'll enter the land of Crete Senesi, famed for it's unusual soil that produces some extraordinary vistas. A big highlight today is the town of Asciano, we recommend taking lunch here before a short ride onwards to your hotel in the nearby countryside.

DAY 4 | Castello di Leonina to Lucignano | Cycle time 2 hours 45 minutes
The quiet country lanes in this part of the world are a delight to ride along and will take you away from the Creta Senesi today to the extraodinary Lucignano. Lucignano is a compact medieval settlement with a rich and vibrant history, so we suggest arriving early, enjoying some lunch and getting to know the town and it's quirky atmosphere.

DAY 5 | Lucignano to Cortona | Cycle time 2 hours
After a night in Lucignano, it's tme to head back toward Cortona. The route takes you through the Val di Chiana, home to Chianina cattle, one of the largest and one of the oldest cattle breeds in the world. These cattle are raised for their beef and our carnivorous guests will definitely enjoy a steak in these parts, the local cut of choice is a Fiorentina. Before long you'll spot the white outline of Cortona in the distance, guiding you in towards another great nights sleep.

DAY 6
After your final long, lazy breakfast in the Tuscan hills, we say “Arrivederci”.

Please note that our itinerary may vary slightly for our indulgence accommodation category. For details, speak to one of our Activities Experts on 020 7471 7760.

This tour is operated by our preferred local partner.

Your Cycling Holidays in Tuscany & Umbria

Tuscan Valleys eBike Holiday | Self Guided

Classic Tour

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 your first taste of Umbrian cuisine.

DAY 2 | Cortona to Montefollocino | Cycle time 2 hours 10 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 Montefollocino, where you will stay the night, through spectacular scenery that typifies everything you’ve always envisaged Tuscany to be.

DAY 3 | Montefollocino to San Quirico d'Orcia | Cycle time 1 hours 50 minutes
Yet more verdant panoramas await today as you venture deeper into Tuscany through rolling vineyards. From Montefollocino, you'll cycle towards Petroio and Castelmuzio, the latter of which is our preferred lunch spot on this day. After lunch you will pass the Monestry of S. Anna in Camprena, famous for it's use in The English Patient amongst other things. You end your ride in San Quirico d'Orcia, one of the regions most picturesque medieval towns.

DAY 4 | San Quirico d'Orcia Rest Day or Optional Round Trips
A choice is available today. Either spend the day relaxing in San Quirico, wandering the postcard perfect streets and exploring the tastes of Tuscany, both on your plate and in your wine glass. If you long for another day in the saddle, there are round trip options of 1 hour 45 minutes and 3 hours in duration, taking in the countryside and some charming towns in the surrounding area.

DAY 5 | San Quirico d'Orcia to Castello di Leonina | Cycle time 2 hours 40 minutes
Today you'll ride through a dramatic change of scenery as you enter the Crete Senesi, where the characteristic mattaione soil can produce some unusually mesmerising vistas. The halfway point today is Asciano, where you will want to stop and explore the streets on foot. We advise lunch here too, perhaps a wood fired pizza in La Mencia, our favourite spot. Your route then winds north-west towards Siena, dropping you off at Castello di Leonina.

DAY 6 | Castello di Leonina to Lucignano | 2 hours 45 minutes
The quiet country lanes in this part of the world are a delight to ride along and will take you away from the Creta Senesi today to the extraodinary Lucignano. Lucignano is a compact medieval settlement with a rich and vibrant history, so we suggest arriving early, enjoying some lunch and getting to know the town and it's quirky atmosphere.

DAY 7 | Lucignano to Cortona | Cycle time 2 hours
After a night in Lucignano, it's tme to head back toward Cortona. The route takes you through the Val di Chiana, home to Chianina cattle, one of the largest and one of the oldest cattle breeds in the world. These cattle are raised for their beef and our carnivorous guests will definitely enjoy a steak in these parts, the local cut of choice is a Fiorentina. Before long you'll spot the white outline of Cortona in the distance, guiding you in towards another great nights sleep.

DAY 8
After your final long, lazy breakfast in the Tuscan hills, we say “Arrivederci”.

Please note that our itinerary may vary slightly for our indulgence accommodation category. For details, speak to one of our Activities Experts on 020 7471 7760.

This tour is operated by our preferred local partner.

Your Cycling Holidays in Tuscany & Umbria

Tuscan Valleys eBike Holiday | Self Guided

  • Parco Fiorito, Cortona

    Classic - 4 Star

    A charming luxury 'agriturismo' nestled in a tranquil portion of the countryside outside Cortona. The hotel has a lot of outdoor space for enjoying the fantastic Umbrian weather, complete with a large outdoor pool. Back inside, you'll find a great restaurant and a selection of wellness facilities.

  • La Chiusa Hotel & Restaurant, Montefollonico

    Classic & Indulgence - 3 Star

    La Chiusa Hotel & Restaurant sits on the edge of Montefollonico offers some of the best views available of the stunning Tuscan landscape. Enjoy a glass of red on the terrace and soak up the views before tucking in to delicious regional fayre in the restaurant.

  • La Dimore del Capitano, San Quirico d'Orcia

    Classic - 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.

  • Castello di Leonina Relais, Asciano

    Classic & Indulgence - 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.

  • Le Casselle, Lucignano

    Classic & Indulgence - Charming B&B

    Le Casselle is a small, charming B&B with a lot of outdoor space and fantastic swimming pool. The welcome is warm and the breakfasts fantastic.

  • Villa di Piazzano, Cortona

    Indulgence - 4 Star

    Dating back to 1464, the Villa di Piazzano is an elegant Historic Estate set on the border between Umbria and Tuscany. Cardinal Silvio Passerini originally built the villa as a hunting lodge. It is located close to Cortona, tucked away in beautiful Italian countryside and a protected natural reserve.

  • Palazzo del Capitano, San Quirico d'Asciano

    Indulgence - 4 Star

    Part of a collection of hotels in the town, the Palazzo del Capitano sits at the top of the tree in terms of luxury. The rooms are generally large and decorated in a classy, classical manner. There are spa facilities available and outdoor spaces for unwinding at the end of a warm Tuscan summers day.

Your Cycling Holidays in Tuscany & Umbria

Tuscan Valleys eBike Holiday | Self Guided

Tour Only | 2019

Departure Date

Nights Category Board Basis Adult Price  
April - October 2019 5 Classic B&B £905 Enquire Now
April - October 2019 5 Classic Half Board £1065 Enquire Now
April - October 2019 5 Indulgence B&B £1185 Enquire Now
April - October 2019 5 Indulgence Half Board £1395 Enquire Now
April - October 2019 7 Classic B&B £1165 Enquire Now
April - October 2019 7 Classic Half Board £1405 Enquire Now
April - October 2019 7 Indulgence B&B £1565 Enquire Now
April - October 2019 7 Indulgence Half Board £1825 Enquire Now

Package Prices (Flights and Transfers Included) | 2019

Departure Date

Nights Category Board Basis Adult Price  
April - October 2019 5 Classic B&B £1215 Enquire Now
April - October 2019 5 Classic Half Board £1385 Enquire Now
April - October 2019 5 Indulgence B&B £1505 Enquire Now
April - October 2019 5 Indulgence Half Board £1705 Enquire Now
April - October 2019 7 Classic B&B £1485 Enquire Now
April - October 2019 7 Classic Half Board £1725 Enquire Now
April - October 2019 7 Indulgence B&B £1885 Enquire Now
April - October 2019 7 Indulgence Half Board £2135 Enquire Now

Single Supplements:

5 Nights Classic: £180 pp

5 Nights Indulgence: £375 pp

7 Nights Classic: £275 pp

7 Nights Indulgence: £425 pp

Please note, a 10-night itinerary is available on request.

Your Cycling Holidays in Tuscany & Umbria

Tuscan Valleys eBike Holiday | Self Guided

Your Cycling Holidays in Tuscany & Umbria

Tuscan Valleys eBike Holiday | Self Guided

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