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Your Cycling Holiday in Umbria

Indulgence | The Grand Tour of Umbria | Self Guided

An indulgent escape to Umbria, this leisurely self-guided cycling holiday is filled with delicious food and romantic scenery. Cycle along the ancient roman Via Flaminia, the ancient highway of emperors and traders, as you visit charming towns and forgotten ruins.

Our Umbrian e-bike tour is the most luxurious way to experience Italy's 'Green Heart'. Cycle through verdant valleys and explore the vibrant towns that lie between them. Thanks to your e-bike, you'll make short work of any hill, which means you can reach those viewpoints and enjoy the scenery with minimal effort. 

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

Your Cycling Holidays in Umbria

Indulgence | The Grand Tour of Umbria | Self Guided

DAY 1 | Arrive at Perugia, Florence or Rome airport and head 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 | Round Trip: Tuoro-sul-Trasimeno | 50 km | Cycle time 2 hours 50 minutes 
Our local team will meet you in the morning to get you set up on your e-bikes and talk you through the plan for your tour before seeing you off on your first-round trip ride. The route today heads east into the Val di Pierle, before climbing and descending into the Niccone valley. This valley, now a peaceful, agricultural area, has frequently served as a frontier throughout history – often between warring parties. You’ll pass the dramatic Pierle Castle on your descent, one of the many fortifications throughout the length of the valley. From here, another twisting climb opens up to a spectacular viewpoint of the lake at Gosparini. The ride finishes passing through Tuoro-sul-Trasimeno, famous as the site of Hannibal’s battle with the Romans in 217 BC, before returning towards Cortona. 

or

Castiglione-del-Lago | 47 km | Cycle time 2 hours 35 minutes
The second option for rides today takes you to Castiglione-del-Lago. This is a beautiful town, perched on a peninsula and offering fantastic views of Lake Trasimeno. There are a host of excellent restaurants for lunch on the cobbled streets of the old town area. take a dip in the lake before retuning to Cortona in the afternoon.

DAY 3 | Cortona to Montone | 43km | 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 4 | Montone to Gubbio | 50km | 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 5 | Gubbio to Assisi | 54km | 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 6
After your final caffè latte this morning, we say “Arrivederci”.

Your Cycling Holidays in Umbria

Indulgence | The Grand Tour of Umbria | Self Guided

DAY 1 | Arrive at Perugia, Florence or Rome airport and head 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 | Round Trip: Tuoro-sul-Trasimeno | 50 km | Cycle time 2 hours 50 minutes 
Our local team will meet you in the morning to get you set up on your e-bikes and talk you through the plan for your tour before seeing you off on your first-round trip ride. The route today heads east into the Val di Pierle, before climbing and descending into the Niccone valley. This valley, now a peaceful, agricultural area, has frequently served as a frontier throughout history – often between warring parties. You’ll pass the dramatic Pierle Castle on your descent, one of the many fortifications throughout the length of the valley. From here, another twisting climb opens up to a spectacular viewpoint of the lake at Gosparini. The ride finishes passing through Tuoro-sul-Trasimeno, famous as the site of Hannibal’s battle with the Romans in 217 BC, before returning towards Cortona. 

or

Castiglione-del-Lago | 47 km | Cycle time 2 hours 35 minutes
The second option for rides today takes you to Castiglione-del-Lago. This is a beautiful town, perched on a peninsula and offering fantastic views of Lake Trasimeno. There are a host of excellent restaurants for lunch on the cobbled streets of the old town area. take a dip in the lake before retuning to Cortona in the afternoon.

DAY 3 | Cortona to Montone | 43km | 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 4 | Montone to Gubbio | 50km | 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 5 | Free Day or Optional Round Trip to vineyards | 33km | Cycle time 1 hour 50 minutes
Today, you have the chance to explore the gorgeous and historic Gubbio. Take a stroll through its cobbled streets and visit all its artisan shops. For those wanting to get back in the saddle, there is a route which takes you through the local vineyards and a wine producer where you can have a tasting.

DAY 6 | Gubbio to Assisi | 54km | 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 7 | Rest Day or Optional Round Trip to Spello or Basta Umbria | 59 or 37km | Cycle time 2 hours - 3 hours 40 minutes
Today, explore Assisi to your heart's content with its many cafes and restaurants to discover. If you're itching to cycle some more, you have the option of two more routes. Either pedal to the charming town of Spello in the south or to the wineries of Bastia Umrbia.

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

Your Cycling Holidays in Umbria

Indulgence | The Grand Tour of Umbria | Self Guided

  • Villa di Piazzano, Cortona

    5 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 the beautiful Italian countryside and a protected natural reserve.

  • La Locanda del Capitano, Montone

    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

    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

    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.

  • Hotel Giotto, Assisi

    4 Star

    Located in the centre of Assis, the beautiful Hotel Giotto boasts fantastic views of the town. With sun-drenched terraces and their own spa, it's not hard to find a space for relaxation here. Describing themselves as unique and timeless, you can't help but agree when you see the stylish interiors. 

  • Monastero di Cortona, Cortona

    5 Star

    A historic monastery dating back to the 15th century, which opened its new doors in 2019 as an elegant boutique hotel, after careful renovation works carried out in compliance with the Arezzo Monuments and Fine Arts Office and the environment. The original monastery structure can be seen in the hotel's layout, in the beamed and vaulted ceilings, in the frescoes that have been recovered and restored, in the imposing corridors, and in the loggias.

Your Cycling Holidays in Umbria

Indulgence | The Grand Tour of Umbria | Self Guided

Tour Dates & Prices

Available Duration Tour Only Package
(Flights & Transfers Included)
Self Drive
(Eurotunnel Included)
Board Basis
1st Apr 2024 to 31st Oct 2024 5 Nights £1,695pp Bed & Breakfast
1st Apr 2024 to 31st Oct 2024 5 Nights £1,825pp B&B + 4 Dinners
1st Apr 2024 to 31st Oct 2024 7 Nights £2,225pp Bed & Breakfast
1st Apr 2024 to 31st Oct 2024 7 Nights £2,385pp B&B + 4 Dinners

This tour has set scheduled departures with specific start days. If you’d like to start your holiday on another date, enquire about our private departures.

private departure supplements are £75.

5 Nights - Thursday Departure

*Where tour pricing is displayed in your local currency, please note this is for indicative purposes and your final holiday will be confirmed and transacted at the time of booking with our team in Pound Sterling.

Your Cycling Holidays in Umbria

Indulgence | The Grand Tour of Umbria | Self Guided

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