Your Cycling Holidays in Italy

Treasures of Tuscany and Umbria

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. Take a tour around a genuine, traditional Tuscan castle on Day 2 and around the historic town of Assisi on Day 5.

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.

We love: the fully guided versions of our Tuscan tours which take you off the beaten track to the local eateries, including a dinner prepared and cooked for you on Day 2 by celebrity chef, Giancarlo Polito.  


• Delicious restaurant meals each night
• Bed and breakfast accommodation
• Expert on the spot support
• Luggage carried between your hotels
• Fully serviced touring bikes
• 100% financial security through ABTA and ATOL

This tour is operated by our preferred local partner

Your Cycling Holidays in Italy

Treasures of Tuscany and Umbria


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.  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. (2hr20 cycle time)

DAY 3 Montone to Gubbio. 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. (2hr50 cycle time)

DAY 4 Gubbio to Assisi.  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. (3hr cycle time)

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. 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. (2hr40 cycle time)

DAY 7 Tavernelle di Panicale to Cortona. 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. (2hr40 cycle time)

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.

  • Lake Trasimeno, stunning views at Italy’s largest peninsular lake.

  • Gubbio’s ancient Roman theatre.

  • A traditional Italian lunch made from ingredients taken from the café garden in Umbertide.

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

Your Cycling Holidays in Italy

Treasures of Tuscany and Umbria


A fine selection of hotels to choose from

  • Hotel Ideale

    Hotel Ideale


    Just a short walk from the centre of beautiful Assisi, the Hotel Ideale sits in peaceful rose gardens and boasts a huge terrace, ideal for relaxing in the evening. Some rooms even have balconies that have panoramic views over the historic city. 

  • Villa di Piazzano

    Villa di Piazzano


    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. 

  • Villa Monte Solare

    Villa Monte Solare

    4 star

    Originally the home to 18th century aristocrats, this stunning traditional Italian villa is nestled away in the rolling Umbrian countryside. 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.

  • La Locanda del Capitano

    La Locanda del Capitano

    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.

  • Relais Ducale

    Relais Ducale

    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.

  • Villa Marsili

    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.  

Your Cycling Holidays in Italy

Treasures of Tuscany and Umbria


April to October


7 nights
Full board
20 May
10 June
8 July
9 & 23 September
7 October
5 nights
Full board
20 May
10 Jun
8 July
9 & 23 September
7 October
7 nights B&B
29 April 
until 28 October
5 nights B&B
29 April 
until 28 October
Adult (12+) £2155 £1925 £1425 £1055
Child (7-12) On request On request On request On request
Child (2-6) On request On request On request On request

All prices per person, based on two people sharing and two nights per hotel. Guided and Full-Board Option includes transfers from Perugia, breakfast, 6 lunches with wine, 6 dinners, 6 morning coffee stops and tour entrance fees. Single room supplement: on request.

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