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Your Cycling Holidays in Tuscany & Umbria

Umbria & Tuscany | Self Guided eBike Holiday | SAVE £100 per person

Iconic Italian countryside with fine wines and gastronomic delights

Pedal your way gently along quiet side roads and tracks; travel the ancient 'via Flaminia' highway of the Roman empire; and feast on wondrous Italian fayre and delicious Italian wines.

Our Tuscan e-bike tours are the perfect way to discover the rolling hills of the region. Gone are the days of huffing and puffing your way to the top, e-bikes make light work of the undulating terrain leaving you free to take in the spectacular scenery with the wind in your hair.

Book any Cycling For Softies Italian holiday in December and SAVE £100 per person.

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 ATOL

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

Umbria & Tuscany | Self Guided eBike Holiday | SAVE £100 per person

Classic Tour

DAY 1 | Arrive at Perugia, Florence or Rome airport and transfer to Cortona
Set up in the hills of southern Tuscany with spectacular views of the surrounding valley and Lake Trasimeno, the Tuscan jewel of Cortona is where you’ll begin and end your safari. At your villa you’ll be fitted out with your e-bike and briefed on how to use it before enjoying drinks and dinner.

DAY 2 | Cortona to Montone | Cycle time 2 hours 20 minutes
After breakfast, begin your journey towards the Tuscany and Umbria border to visit ancient castles of the Niccone Valley, then stop mid morning for a delicious coffee. Enjoy lunch in the Upper Tiber Valley before taking the riverside path and country roads to medieval Montone where you can enjoy a fabulous dinner, prepared by none other than celebrity chef, Giancarlo Polito. 

DAY 3 | Montone to Gubbio | Cycle time 2 hours 50 minutes 
Take a typical workers’ lunch in the piazza-side trattoria. Here, we pick up the trail of St. Francis of Assisi to continue our journey, on which spectacular vistas are abundant. Stopping off to explore the second-largest theatre of the Roman Empire, we’ll then arrive in Gubbio, a pretty town set on the slopes of Monte Ingino, known for its medieval palaces and cathedrals.

DAY 4 | Gubbio to Assisi | Cycle time 3 hours
After breakfast on the terrace, ride through the city gate towards the rolling foothills of the Apennine and the Via Flaminia, Rome’s ancient highway to the north. Stop for a coffee break at a lovely cafe, before you savour an unforgettable lunch of typical Umbrian dishes before cycling to Assisi, the birthplace of St.Francis.

DAY 5 | Assisi to Cortona | Cycle time 3 hours 20 minutes
Descend from Assisi and stop to look back at the spectacular view of the town. Your route today mostly follows the Tiber Valley, a landscape dotted with castles and covered with rich, green agricultural land. You'll spot the unmistakebale white outline of Cortona towards the end of the day, where a good nights sleep awaits.

DAY 6
After your final caffè latte this morning, 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.

Your Cycling Holidays in Tuscany & Umbria

Umbria & Tuscany | Self Guided eBike Holiday | SAVE £100 per person

Classic Tour

DAY 1 | Arrive at Perugia, Florence or Rome airport and transfer to Cortona
Set up in the hills of southern Tuscany with spectacular views of the surrounding valley and Lake Trasimeno, the Tuscan jewel of Cortona is where you’ll begin and end your safari. At your villa you’ll be fitted out with your e-bike and briefed on how to use it before enjoying drinks and dinner.

DAY 2 | Cortona to Montone | Cycle time 2 hours 20 minutes
After breakfast, begin your journey towards the Tuscany and Umbria border to visit ancient castles of the Niccone Valley, then stop mid morning for a delicious coffee. You'll then get to experience a fantastic private tour of a genuine, traditional Tuscan castle. Enjoy lunch in the Upper Tiber Valley before taking the riverside path and country roads to medieval Montone where you’ll enjoy a fabulous dinner, prepared by none other than celebrity chef, Giancarlo Polito. 

DAY 3 | Montone to Gubbio | Cycle time 2 hours 50 minutes 
Take a typical workers’ lunch in the piazza-side trattoria. Here, we pick up the trail of St. Francis of Assisi to continue our journey, on which spectacular vistas are abundant. Stopping off to explore the second-largest theatre of the Roman Empire, we’ll then arrive in Gubbio, a pretty town set on the slopes of Monte Ingino, known for its medieval palaces and cathedrals.

DAY 4 | Gubbio to Assisi | Cycle time 3 hours
After breakfast on the terrace, ride through the city gate towards the rolling foothills of the Apennine and the Via Flaminia, Rome’s ancient highway to the north. Stop for a coffee break at a lovely cafe, before you savour an unforgettable lunch of typical Umbrian dishes before cycling to Assisi, the birthplace of St.Francis.

DAY | 5 Rest day in Assisi 
Although your e-bike has helped you effortlessly glide up every hill, it’s still nice to rest your legs today, and explore this beautiful town. There is an optional private tour, or you can simply wander the cobblestone streets, drinking in Assisi’s medieval architecture and artistry.

DAY 6 | Assisi to Bagnaia | Cycle time 2 hours 40 minutes
Descend into the broad Assisi valley, heading west, and recharge mid morning at a local cafe. Then head to Torgiano, where you can taste Lungarotti, the best known of Umbria's wines. Take some time to wander around the wine and olive oil museums in the town. The afternoon gentle ride continues towards the rolling hills of Bagnaia.

DAY 7 | Bagnaia to Cortona | Cycle time 2 hours 40 minutes 
A short ride soon reveals the shores and expanse of Lake Trasimeno. Enjoy a delightful mid morning coffee in San Feliciano, then lunch in the Passignano. Then leave the lake behind and meander back to Cortona via the battlefield where Hannibal routed the Romans in 217 BC.

DAY 8 | Tour ends in Cortona
After your final caffè latte this morning, 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.

Your Cycling Holidays in Tuscany & Umbria

Umbria & Tuscany | Self Guided eBike Holiday | SAVE £100 per person

  • 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.

  • Hotel Fortebraccio, Montone

    Classic - 3 Star

    A newly renovated property that sits juts outside the medieval walls of Montone. The views from the hotel, particularly from the swimming pool, are enchanting and typical of this part of the worlds verdent landscape. An on site restaurant combines international and regional inspiration with fresh ingredients to offer a rich and varied menu.

  • Relais Ducale, Gubbio

    Classic - 4 Star

    Symbol of the town history for being the house of the Duke Federico da Montefeltro, the Relais Ducale, is located in the heart of Gubbio, on the square Piazza della Signoria, considered one of the most beautiful suspended squares of Italy.

  • Hotel Ideale, Assisi

    Classic - 3 Star

    A beautiful hotel overlooking Assisi. It is ideally located at a 5-minutes' walk from the historic centre. Note this hotel is bed & breakfast only.

  • Agriturismo Il Tiro, Bagnaia

    Classic - Agriturismo

    A warm and welcoming agriturismo situated in a calm, rural setting southwest of Perugia. There is a large garden to relax in after a day on the bike, complete with a beautiful swimming pool. The restaurant serves up traditional Umbrian cuisine, crafted with locally sourced produce and the cellar of over 400 regional and international wines will have the perfect bottle to compliment any meal.

  • 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.

  • La Locanda del Capitano, Montone

    Indulgence - 3 Star

    Nestled away in the walled village of Montone, La Locanda del Capitano is a small but perfectly formed hotel and restaurant. The restaurant is run by celebrity chef Giancarlo Polito, serving traditional dishes with a contemporary twist of the highest standard.

  • Park Hotel Ai Cappuccini, Gubbio

    Indulgence - 4 Star

    A restored 17th century monastery that has been restored and converted in to a hotel with the utmost attention to detail. The splendid building has a history that is closely entwined with that of Gubbio itself and its position offers a sense of seclusion and peace, but with easy access to the town itself. There is a fine dining restaurant, an art gallery and a serene parkland area on site.

  • Nun Assissi Relais & Spa, Assisi

    Indulgence - 5 Star

    A timeless and unique destination in the heart of Assisi, this ancient monastery blends its rich history with an array of elegant contemporary stylings to produce a charming, stylish and welcoming feel. The on site restaurant offers a mouth-watering menu, complimented by an extensive list of local wines, alongside some of the best spafacilities in the region.

  • Villa Monte Solare, Tavernelle di Panicale

    Indulgence - 4 Star

    Originally the home to 18th century aristocrats, this stunning traditional Italian villa is nestled away in the rolling Umbrian countryside in Tavernelle di Panicale. With its antique and original decor, the hotel houses just 25 rooms, a deluxe spa and wellness facility, a heated outdoor swimming pool and a tennis court.

Your Cycling Holidays in Tuscany & Umbria

Umbria & Tuscany | Self Guided eBike Holiday | SAVE £100 per person

Tour Only | 2019

Departure Date

Nights Category Board Basis Adult Price  
April - October 5 Classic B&B £805 Enquire Now
April - October 5 Classic Half Board £935 Enquire Now
April - October 5 Indulgence B&B £1185 Enquire Now
April - October 5 Indulgence Half Board £1395 Enquire Now
April - October 7 Classic B&B £1095 Enquire Now
April - October 7 Classic Half Board £1275 Enquire Now
April - October 7 Indulgence B&B £1615 Enquire Now
April - October 7 Indulgence Half Board £1895 Enquire Now

Package Prices (Flights and Transfers Included) | 2019

Departure Date

Nights Category Board Basis Adult Price  
April - October 5 Classic B&B £1120 Enquire Now
April - October 5 Classic Half Board £1245 Enquire Now
April - October 5 Indulgence B&B £1505 Enquire Now
April - October 5 Indulgence Half Board £1705 Enquire Now
April - October 7 Classic B&B £1405 Enquire Now
April - October 7 Classic Half Board £1585 Enquire Now
April - October 7 Indulgence B&B £1925 Enquire Now
April - October 7 Indulgence Half Board £2215 Enquire Now

Single Supplements:

5 Nights Classic: £170 pp

5 Nights Indulgence: £375 pp

7 Nights Classic: £245 pp

7 Nights Indulgence: £525 pp

Your Cycling Holidays in Tuscany & Umbria

Umbria & Tuscany | Self Guided eBike Holiday | SAVE £100 per person

Your Cycling Holidays in Tuscany & Umbria

Umbria & Tuscany | Self Guided eBike Holiday | SAVE £100 per person

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