hillside town with poppyfield in foreground

Experience the best of Umbria

Umbria Cycling Holiday

The sweeping vistas of Umbria are absolutely breathtaking. Rolling hills carpeted with vineyards and olive groves extend endlessly into the distance. #Lovevelo #LoveCycling #Ridefurther

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From
£995
Where
Umbria, Italy
Dates & Duration
Any Dates, Any Duration
Start
Assisi
Finish
Assisi

Cycling Holiday in Umbria

What to Expect on This Trip

  1. Assisi. Ride through olive groves to the hometown of St. Francis and admire the stunning Basilica with sweeping valley views.
  2. Lake Trasimeno. Cycle around Italy’s fourth-largest lake and relax in lakeside villages like Passignano sul Trasimeno.
  3. Montefalco. Known as the ‘Balcony of Umbria’, this hilltop town offers panoramic views and famous Sagrantino wines.
  4. Spoleto. A mix of Roman history and medieval charm with quiet roads leading to ancient aqueducts and hidden piazzas.
  5. Umbrian Life. Discover authentic Italy as you pedal through sunflower fields, stone villages, and peaceful countryside.
This is a trip that goes from place to place
Accommodation

Your accommodation will be in great hotels, expertly picked for their locations and surroundings.

Great Bikes

We have a variety of bikes for you to explore Umbria including flat bar hybrid bikes, e-bikes and road bikes.

Airport & Luggage Transfers

We will provide you with airport transfers and luggage transfers to take your belongings from hotel to hotel.

Digital Route Pack

As part of your cycling adventure, we will provide you with our curated set of digital routes. Just download to your Garmin or Wahoo, or navigate from your phone.

Arrive & Depart At Any Time

Your Day by Day Itinerary

  1. Day 1 - Arrive into Assisi

    Touch down in the spellbinding town of Assisi, where ancient stories echo through cobbled streets and spiritual history meets scenic charm. This UNESCO World Heritage gem is your gateway to Umbria. Wander through winding alleys and stumble across hidden piazzas, each one whispering tales of Saints Francis and Clare. Marvel at the grandeur of the Basilica of St. Francis, explore the Roman Temple of Minerva, and soak up the serenity that wraps around this hilltop town. In the late afternoon, it’s time to meet your trusty steed—your bike, that is. After a relaxed fitting and a route briefing, you’ll settle in for the night at a cosy 3- or 4-star hotel just steps from the old town.

  2. Day 2 - Ride the Valley of Spoleto to Torgiano

    64km total distance

    Your wheels hit the road with a peaceful morning pedal to the charming village of Spello. From there, ride through the sun-drenched valley of Spoleto, passing the bustling town of Foligno before the road rises to Montefalco—affectionately called the “balcony of Umbria.” The views are jaw-dropping, and the frescoed Franciscan church museum is well worth a peek. Descend into Bevagna, where medieval magic lives on in its perfectly preserved square and Romanesque churches. The day wraps up in Torgiano, a hilltop haven with a brilliant wine museum and tempting tastings at Lungarotti. You’ll rest your legs in a stylish 3- or 5-star hotel.

    Distance: 64 km | Ascent/Descent: +552m

  3. Day 3 - Culture and Coffee in Perugia

    34km total distance

    Today’s ride takes you to Perugia, the lively capital of Umbria, buzzing with Renaissance art, ancient arches and café culture. This hilltop city is bursting with character, from its medieval old town to its vibrant piazzas. After soaking up its energy, you’ll glide back to the peaceful lanes of Torgiano for a second night in this wine-loving gem.

    Distance: 34 km | Ascent/Descent: +503m

  4. Day 4: -Torgiano to Passignano – Lakeside Living

    51km total distance

    Set off from Torgiano and meander through softly rolling hills, where every pedal stroke brings you closer to Lake Trasimeno’s shimmering shoreline. The reward? A breathtaking panorama of Italy’s fourth-largest lake, dotted with islands that seem to float in time. Ride through the sleepy fishing village of San Feliciano—where ferries drift lazily toward Polvese Island—then follow the gentle crunch of gravel paths all the way to Passignano. This lakeside gem is where history and nature dance in harmony. Wander its historic lanes, stretch out on the beach near the town centre, or hop over to the charming Isola Maggiore for a splash of island life. Tonight, you'll stay in a welcoming 3- or 4-star hotel, just steps from the water.

    Distance: 51 km | Ascent/Descent: +472m

  5. Day 5 - From Trasimeno to Umbertide – Hills and Heritage

    It’s time to trade lake views for unspoiled hills and medieval towers as you ride toward the tranquil town of Umbertide. The route winds up to Castel Rigone, perched high above the lake with knockout views in every direction. From here, it’s pure joy riding along a scenic ridge before descending smoothly into the Tiber Valley. Umbertide welcomes you with its iconic 14th-century tower and a sense of quiet charm. Tonight, you're tucked away just outside town in a country hotel with a fantastic on-site restaurant and a pool that’s perfect for a refreshing dip after a rewarding day in the saddle.

    Distance: 47 km | Ascent/Descent: +837m

  6. Day 6 - From Umbertide to Gubbio – Timeless Hilltop Towns

    58km total distance

    Roll out of Umbertide and prepare for a day that’s all about classic Umbrian charm and big-sky views. Your first climb brings you to Montone, a little town where time seems to have slowed down just for you. Cobbled streets, quiet corners, and a view that makes every turn of the pedal worthwhile. From there, you’ll head on to Pietralunga, another sleepy hilltop hideaway, before descending into the majestic fortified town of Gubbio. With its Roman theatre, ancient palaces, and the monastery of Saint Ubaldo perched 827 metres above the town, Gubbio is an open-air museum with serious wow-factor. If you’re up for it, take the quirky cable car to the top and soak in those sweeping views. You’ll stay overnight in a cosy 3- or 4-star hotel near the historical centre.

    Distance: 58 km | Ascent/Descent: +904m

  7. Day 7 - Gubbio to Assisi

    59km total distance

    Your final day kicks off with a punchy climb through Umbrian countryside that looks like it was painted just for you—rolling hills, patchwork fields, and silence that soothes the soul. After that early effort, enjoy the long, glorious descent into Assisi. This ride doesn’t just end with a bang—it rolls you right through the heart of the town. You’ll cruise past the monumental Basilica of St. Francis, the Temple of Minerva, and the Basilica of Saint Clare, each one a beautiful bookmark in your week-long story. Your journey comes full circle with an overnight stay in Assisi, giving you one last chance to soak up its spiritual charm.

    Distance: 59 km | Ascent/Descent: +807m

  8. Day 8 - Departure

    Today we bid you arrivederci and will organise for your transfer back to the airport.

Make An Enquiry

We are the cycling holiday experts.

Whether you're a keen road cyclist, enjoy riding an e-bike or hybrid bike, or want to get your family more active, we have the perfect cycling holiday for you.

Reviews

What our Cyclists Say

Awesome customer Service like it used to be. When planning my husband's 50th birthday and knowing very little about cycling I decided to try Love Velo and I can't recommend them, and the service I've received from James Danvers highly enough.

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Abby

I booked through Love Velo because the reviews were so good. I wasn't disappointed. Right from my first contact with LV they were easy to talk to and although I dithered (my first cycling trip abroad) they didn't press me. When I eventually confirmed my booking they took care of everything.

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Stephen

Everything about Love Velo has been faultless. From the initial notification of them teaming up with Le Col and to the pricing being unbelievable and then the customer service, top class. James, if all the staff are as attentive to every detail as you are then everyone will be as lucky as I have been. 100% at some point, hopefully in the near future I will be booking again with you guys. Thank you again

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Ian

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Umbria through your lens

Join Us on An Umbrian Bike Tour

Why us

Why book with Love Velo?

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FAQs

Umbrian Cycling Holiday FAQs

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