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Your Cycling Holidays in Tuscany & Umbria

Treasures of Tuscany and Umbria | Guided Group | SAVE £100 per person

Expert guided group cycling tour in to the wonderful Umbrian countryside

Starting on the Tuscany borders, this magical, seven night, eight day e-bike tour is a ‘gourmet adventure’ in to the hills and valleys of classic Umbria.

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 Tuscany and Umbria 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

  • Six delicious lunches with wine and six dinners

  • Private tours, events, entrance fees, gratuities & tips

  • Delightful premium accommodation

  • Expert local group leader

  • Luggage carried between your hotels

  • Fully serviced electric bikes

  • Support vehicle for the group

  • 100% financial security through ABTA and ATOL

Group size : Maximum 8 people plus local leader.

Your Cycling Holidays in Tuscany & Umbria

Treasures of Tuscany and Umbria | Guided Group | SAVE £100 per person

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 a first drinks and dinner with your group.

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 enjoy 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 feast on 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”.

The distances may seem a little further than our usual tours, but thanks to the power assisted e-bikes which are provided as standard, the hills will be a breeze!

Not to be missed:

  • Celebrity chef, Giancarlo’s dinner with fine wine tasting throughout.

  • Six lunches including wine and six delicious dinners.

  • Private Tours, Events, Entrance Fees, Gratuities & Tips.

  • Gubbio’s ancient Roman theatre.

  • The four stunning historic castles in the Niccone Valley, with a private tour of a Tuscan castle.

This tour is operated by our preferred local partner.

Your Cycling Holidays in Tuscany & Umbria

Treasures of Tuscany and Umbria | Guided Group | SAVE £100 per person

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 a first drinks and dinner with your group.

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 enjoy 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 feast on 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 Tavernelle di Panicale | 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 Cantina Goretti, where you can taste L’Arringatore, the wine of the Pope and a light lunch. The afternoon gentle ride continues towards the rolling hills of Panicale.

DAY 7 | Tavernelle di Panicale 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, then lunch in the vineyard with local wine tasting. Then meander back to Cortona via the battlefield where Hannibal routed the Romans in 217 BC.

DAY 8 
After your final caffè latte this morning, we say “Arrivederci”.

The distances may seem a little further than our usual tours, but thanks to the power assisted e-bikes which are provided as standard, the hills will be a breeze!

Not to be missed:

  • Celebrity chef, Giancarlo’s dinner with fine wine tasting throughout.

  • Six lunches including wine and six delicious dinners.

  • Private Tours, Events, Entrance Fees, Gratuities & Tips.

  • Gubbio’s ancient Roman theatre.

  • The four stunning historic castles in the Niccone Valley, with a private tour of a Tuscan castle.

This tour is operated by our preferred local partner.

Your Cycling Holidays in Tuscany & Umbria

Treasures of Tuscany and Umbria | Guided Group | SAVE £100 per person

  • Villa di Piazzano, Cortona

    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

    4-star

    Nestled away in the wall 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

    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.

  • Castello Petrata, Assisi

    4-star

    This rural hotel overlooks the town of Assisi. There is a spa and a restaurant serving delicious local food. There is also a swimming pool and the option to take a taxi into Assisi for the evening.

  • Villa Monte Solare, Tavernelle di Panicale

    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

Treasures of Tuscany and Umbria | Guided Group | SAVE £100 per person

Guided Group Dates and Prices | 2019

Departure Dates Nights Adult Tour Only Price  
25th May – 1st June 7 £2295 Enquire Now
8th June – 15th June 7 £2295 Enquire Now
31st August - 7th September 7 £2295 Enquire Now
28th September - 5th October 7 £2295 Enquire Now

Prices are based on two people sharing a twin or double room.

Group size maximum : 8 per group plus local leader

Single Occupancy : £50 per night

5 Day Guided Group Itinerary
We  can also offer a shorter 5 day Guided Group itinerary. Please ask our Activities Experts for more information.

Your Cycling Holidays in Tuscany & Umbria

Treasures of Tuscany and Umbria | Guided Group | SAVE £100 per person

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