Cycling in The Heart of Umbria

8 Days & 7 Nights 4.8 Read 10 reviews
  • Pedal through the impossibly beautiful landscapes of Umbria.
  • Experience true Italian hospitality in a typical Umbrian farmhouse.
  • Marvel at Giotto’s frescos in the Basilica Di San Francesco.
  • Make sure to sample the delicious regional cuisine along the route.
  • Explore the UNESCO site of Assisi, the birthplace of St Francis Italy's patron saint.
Take time to explore the most famous hill towns of Cortona, Perugia, Assisi and the charming Spello. Stop en route to visit one of many wine cantinas and sample their delicious local wine. On this relaxed cycling tour pedal through the mesmerising and beautiful Umbrian countryside. Your journey begins at the medieval and bustling town of Cortona and takes you south to the enchanting Lake Trasimeno with its pretty lakeside towns. Unwind as you cycle in the beautiful silvery green landscape of olive groves, west of Perugia. Cycle among vineyards and medieval hamlets before heading to the marvels of Perugia and Assisi. The tour ends with an unforgettable ride to reach the flower-filled cobbles streets of Spello - one of the best preserved medieval towns in Umbria. The combination of warm Umbrian hospitality, unforgettable local food and wine and medieval hilltop towns, together with the relaxed pace of the tour, makes this an unforgettable biking trip in the heart of Umbria.
Read All
This holiday will appeal to anyone who can ride a bicycle and wants to enjoy a relaxing cycling holiday, in the rolling Umbrian Countryside, while exploring the areas medieval towns.

Tour Type:

Slower Adventures | Where walking and cycling meet easy-going exploring, our Slower Adventures are the perfect combination. Most days are filled with picturesque journeys with some free time to dive into the destination and experience the people, local food and culture as you go.


Leisure Cycling | Leisure Cycling

This trip is suitable for:

Solo Travellers

As a guide, we would suggest that the minimum age of traveler this tour would be suitable for is: 5 Years

Ideal if you have an interest in:

  • Foodie
  • Wine

Activity Level & Terrain

This cycling tour is graded easy to moderate. The routes follow surfaced country roads and secondary roads for the most part. Near larger towns and cities there are some sections on busier roads.


Navigation, Route Notes & Maps

The route is well signposted and way marked and your info pack along with maps will be suffice for directions to your each destination.  There will be the occasional other cyclist around in case you are looking for help. A detailed information pack including route notes, local information and maps will be included in the trip.



One of the highlights of this tour is the high standard of the accommodation. We specifically choose the hotels and agriturismo (country hotels) to ensure that you enjoy every minute of your stay. All offer a warm Italian welcome to walkers, traditional hospitality and delicious local food and drink. Details of the lovely local hotels we normally use are detailed below.

Accommodation Details

We will always try and accommodate you at the locations detailed below, but because of limited availability we may have to accommodate you at an alternative location of the same or better standard. Alternative details will be noted on your accommodation sheet.

Single Rooms

This independent walking holiday is not available to solo walkers. If you require single rooms in your party we will of course try to accommodate your request, subject to availability and payment of a single supplement.


The delicious Italian food and wine available locally is undoubtedly a highlight of this holiday. The price of your holiday includes a hearty breakfast each morning. Lunch and dinner are not included so you are free to choose from the available options. Most of your accommodations will more than happy to provide a packed lunch on request and this can be booked on arrival. Alternatively your route includes details of local shops and convenient lunch stops on the way. Dinner is available either at your accommodation or nearby restaurants.

  • Personal briefing and support from our local representative
  • 7 nights accommodation including breakfast
  • Door to door baggage transfer
  • A detailed info pack, route notes and map
  • Emergency telephone support from our local representative and UK office in the event of a problem
  • Travel insurance (required)
  • Bike and helmet hire
  • Travel to Cortona
  • Lunches and dinners
  • Snacks and drinks
  • Optional cooking course on day 3
  • Taxi transport or public transport should you need to skip a stage
  • Optional cooking course on day 3
  • Airport transfers

When To Go


Our Cycling in the Heart of Umbria Holiday is available from April to October. You can start your holiday on any date in the season. Please note that July and August are the hottest months. Make sure to always take plenty of water to stay hydrated and wear sunscreen or sun-protective clothing, especially on very hot days. To make a provisional reservation select "Book" and select any options required.

Getting to the Start

By Air

We recommend you fly to Rome, Florence, Pisa or Perugia and take the train to Terontola rail station from where you can take a local taxi the short distance to Cortona. If you phone our local partner on arrival they can arrange this taxi for you.

Trains run regularly and take 2h00, 1h30, 2h30, or 1hr respectively. Tickets can be booked on arrival, or online prior to departure. You can also fly directly to Perugia with the low cost airline Ryanair, from London Stansted.

From Florence Airport

Buses and taxis from the airport to the City Centre take around 25 or

15 minutes respectively and cost 4.50/20 euro. From Florence main train station (Firenze M Novella) take the train to Terontola rail station (1hr30 approx).

From Pisa Airport

There is a train station at Pisa Airport which can be used to reach Pisa Central station from where you can catch the train to Terontola (2hr30 approx).

Pre-Booked Taxi/Minibus

We can pre book airport transfers for you, please ask us for a quote.

Getting from the End

To Florence/Pisa/Rome/Perugia

From Spello our local partner will transfer you back to Assisi or Foligno station for onward travel by train or Perugia Airport.

Travel to Florence/Pisa/Rome/Perugia takes 2hr30, 4hr10, 2hr30, and 30mins respectively.

Luggage Transfer

Baggage Transfer

Your bags will be collected from your accommodation each day and moved onto your overnight accommodation. We ask you to limit your luggage to one bag of up to 20kg per person.

General Information

General Information

The distances and ascent/descents are approximations of the recommended routes. Please be prepared by packing all necessary items, for example, proper rain gear (jacket and pants), sun hat and sun screen. Your information pack has a detailed equipment list which includes standard walking/cycling gear such as good walking boots or shoes, warm and waterproof clothes for the cooler months and lightweight clothing for summer, and a day pack.

Additional nights and extensions

Many of our clients choose to add extra nights along the route to sample more of the area and attractions available. You may wish to request an extra night in Cortona, Perugia or Corte delle Poggio for another cooking lesson!

At the start, or end, of your holiday you may consider a night or two in the beautiful cities of Florence, Rome or even Venice.


Bike Rental(not included)


Answer (example)



Bike Type


Frame types

gents, ladies, unisex



Front suspension




Mud guards


Luggage rack Rear/Front




Handle bar Bag/ map holder

Depends on the bike

Bottle holder/Water bottle


Computer meter


Interchangeable pedals


Front gear set


Back gear set




Helmet included


Puncture repair kit


Spare inner tubes/ how many






Travel Insurance

Travel Insurance

It is a requirement of booking this tour with Macs Adventure that you have suitable Travel Insurance which covers you for the activity, emergency evacuation and hospital care.

How fit do I need to be?
What happens if I can’t cycle a stage?
When is the best time of year?
How far in advance do I need to book?
What personal equipment do I need?
Which is the best airport?


Day 1 Arrive Starting Point: Terontola (Cortona) Day 2 Cycle to Poggio delle Corti - 45 km 28 miles / 45 km Day 3 Poggio delle Corti Loop - 23 or 30 km 18.5 miles / 30 km Day 4 Cycle to Perugia - 32 km 20 miles / 32 km Day 5 Cycle to Assisi - 25 km 15.5 miles / 25 km Day 6 Assisi Circular Loop - 35 km 22 miles / 35 km Day 7 Cycle to Spello - 25 km 15.5 miles / 25 km Day 8 Onward Travel

The Macs Way

  • Tried & Tested Adventures Tried & Tested Adventures
  • Freedom Freedom
  • Book with Confidence Book with Confidence
  • Expertise Expertise
  • Positive Impact Positive Impact
Built with our expert knowledge, to suit you.
  • Knowledgeable and helpful specialist trip planners
  • Wide variety of tours to suit all interests and experience levels
  • Start on any date that suits you
  • Choose your ideal trip length and difficulty
  • Range of accommodation comfort levels
  • Choice of trip styles
Authentic adventure travel experiences on your own terms
  • Choose your own travel companions
  • Walk, cycle and explore at your own pace
  • Make your own decisions
  • Choose your own path
  • Indulge your passions
Feel secure in making the right choice for your precious adventure time
  • 18,000+ unbiased trip & service reviews
  • Feefo Platinum Award 2023
  • 25,000+ travelers trust us each year
  • As featured in the Guardian, Times, Nat Geo Traveler
  • Founder owned & operated since 2003
  • 100+ passionate team members across the US, UK & Europe
You can be confident that every detail of your journey has been expertly planned
  • Carefully planned adventures
  • Quality, hand-picked accommodations
  • Seamless and reliable arrangements
  • Comprehensive trip information & insider tips
  • Detailed maps, route notes and mobile GPS app
  • Helpful 24/7 support should you need it
Travel the right way and make a positive impact
  • Travel responsibly
  • Explore off the beaten track
  • Support locally owned businesses
  • Engage with local communities
  • Minimize your impact
  • Maximize the benefit of your travel
  • Challenge yourself & grow
$ - USD - US Dollar
Country/Region name: