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Italy: Umbria

The Wine Trails of Umbria Cycling

Trip code: C07UR

Average customer rating 5.0 / 5(4 verified reviews)

Self-Guided Cycling
7 nights hotel-to-hotel
Moderate
CO₂ rating 1/5
Headwater Navigation app

Trip highlights

Unspoilt cycling through sun-drenched landscapes: olive groves, boundless vineyards and sunflowers

Superb summer climate, soft terracotta colours, panoramic views

Assisi, the jewel in the Umbrian crown, gorgeous Spello, historic Spoleto, Etruscan Perugia

The medieval wine villages of Montefalco and Torgiano – wine tasting opportunities galore!

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Trip details

Few places can stir emotions quite as intensely as Umbria. To visit here is to embark on a journey into a timeless world of sun-drenched landscapes, ancient hilltop villages and beguiling medieval towns.

What's included

Included

  • 7 nights in 3-star and 4-star accommodation
  • All breakfasts
  • Bike fitting at the start of your holiday
  • Headwater navigation app
  • Bike hire included
  • Luggage transfers between hotels

Not included

  • Flights
  • Local taxes/fees
  • Travel insurance

Your bike

Hand-picked for the route, hire included

Specialized, Hybrid or equivalent. Your bike hire is included in the price of your holiday and comes equipped with the relevant essentials, plus rear pannier.

Travel options

Our travel specialists can arrange flights, rail and transfers to this holiday from wherever you are. Call us to plan your journey. +44 1606 720099

Itinerary

Route map, with each night's stop marked
The full route, night by night. Select the map to view it full screen.

Day 1 · —Arrive in Spoleto

Arrive in Spoleto

Discover the town’s Roman theatre, 12th century Duomo and impressive 14th century viaduct that bridges the valley with spectacular views.

You stay at Hotel dei Duchi

Hotel dei Duchi, Spoleto
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Hotel dei Duchi

Spoleto

  • Air conditioning
  • American Express
  • ATM
  • Bank
  • Hairdryers
  • Mastercard
  • Minibar
  • Safe
  • Television
  • Visa cards

Boasting a prime location in the centre of Spoleto’s historic centre, the Hotel dei Duchi panoramocally gazes out over the town’s Anacajani Park, the Roman theatre and St Agatha’s monastery. Inside, the hotel is stylish and modern, with a lounge and terrace – which benefit from the lovely views – bar and 2 restaurants. Bedrooms at the Hotel dei Duchi are contemporary and comfortable, with views over the valley, the garden or the Roman theatre.

Day 2 · 40km/24.9miSpoleto to Spello

Spoleto to Spello

A gentle ride to start the week’s cycling as you pass the idyllic Fonti di Clitunno, a sacred place of worship to both the Pagans and the Romans. Continue through the valley past sunflower fields and vineyards, with a stunning backdrop of the Teverone hills, before continuing to the medieval town of Spello, with its cobbled streets resplendent with colourful flower boxes.

Elevation

Spoleto to Spello elevation profile

You stay at Albergo il Cacciatore

Albergo Il Cacciatore, Spello
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Albergo il Cacciatore

Spello

  • Air conditioning
  • ATM
  • Bank
  • Hairdryers
  • Market
  • Mastercard
  • Television
  • Visa cards
  • Wifi access

A warm welcome is guaranteed at the Albergo il Cacciatore (the hunter!) as the hotel has been in the same family for over 50 years. Located in Spello’s Old Town, there’s a lovely terrace with an amazing, far reaching view over the valley. Bedrooms here are airy and spacious with a traditional Italian design.

Day 3 · 49km/30.4miAt Spello - loop ride to Bevagna and Montefalco

At Spello - loop ride to Bevagna and Montefalco

Pedal along the Topino river to your first stop of the day, the walled town of Bevagna, home to the 13th century Gothic Palazzo dei Consoli, the golden medieval theatre and Roman temple and baths. Then follow the famous wine route, the ‘Strada del Sagrantino’ uphill to the wine village of Montefalco, known as the balcony of Umbria for its superb panorama. A downhill whizz takes you back on the road to Spello.

Elevation

At Spello - loop ride to Bevagna and Montefalco elevation profile

Day 4 · 31km/19.3miSpello to Torgiano

Spello to Torgiano

Head past olive groves to the medieval, walled village of Cannara, renowned throughout Italy for its red onion festival! There’s the option to detour to the medieval hilltop town of Bettona, known as the ‘Etruscan balcony’ for its superb views and Etruscan origins. End the day in the old wine town of Torgiano, famous for its Lungarotti cellars.

Elevation

Spello to Torgiano elevation profile

You stay at Hotel Al Grappolo d’Oro

HOTEL AL GRAPPOLO DORO, TORGIANO (3 STAR)
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Hotel Al Grappolo d’Oro

Torgiano

  • Air conditioning
  • American Express
  • Bank
  • Hairdryers
  • Market
  • Mastercard
  • Minibar
  • Shops
  • Swimming pool
  • Television

Situated in the centre of the medieval town of Torgiano is Al Grappolo d’Oro (The Golden Bunch of Grapes), a recently restored 19th century residence. The hotel has 15 rooms, each individually decorated in a modern style with warm colours and furnished to a high standard, offering a cosy stay. The art filled reception/lounge area gives the hotel character from the start but features such as the pool in the garden to the rear and the downstairs bar make it a lovely place to relax.

Day 5 · 36km/22.4miAt Torgiano - loop ride to Deruta

At Torgiano - loop ride to Deruta

Lots of options today. Visit the wine and olive oil museum – with tastings – in Torgiano’s centro storico, cycle a circular route to the local ceramics capital of Deruta, or take a taxi to Perugia, capital of Umbria and famous for one of Italy’s finest art collections.

Elevation

At Torgiano - loop ride to Deruta elevation profile

Day 6 · 34km/21.1miTorgiano to Assisi 34km/21mi

Torgiano to Assisi 34km/21mi

Cycle to the sleepy village of Brufa, with its quirky contemporary sculptures perched high on the hilltop, then continue through vineyards, olive groves and wheat fields, before a final climb up to majestic Assisi.

Elevation

Torgiano to Assisi 34km/21mi elevation profile

You stay at Hotel Porta Nuova

Exterior of the Hotel Porta Nuova

Hotel Porta Nuova

Assisi

  • Air conditioning
  • American Express
  • ATM
  • Bank
  • Hairdryers
  • Mastercard
  • Minibar
  • Shops
  • Television
  • Visa cards

Located a stone’s throw from Porta Nuova – one of the main medieval gates into Assisi’s Old Town – the family run Hotel Porta Nuova comes with a contemporary design and modern, well appointed bedrooms. There is a lounge and panoramic terrace on the first floor, where you can relax with a drink whilst admiring the rolling, verdant Umbrian hills.

Day 7 · 13km/8.1mi or 29km/18.0miAt Assisi - loop ride to Sta Maria degli Angeli or Collepino

At Assisi - loop ride to Sta Maria degli Angeli or Collepino

There’s so much to explore in Assisi with its beautiful Piazza del Comune, the 13th century Giotto frescoes and of course, the UNESCO recognised basilica. It’s a short ride (elevation profile below) to Sta Maria degli Angeli to visit its impressive 16th century basilica, or walk up through woods to the Eremo delle Carceri – St Francis’ hermitage – on the flanks of Monte Subasio. Die hard cyclists can take the challenging climb along the Via degli Ulivi to the hilltop, pink hued village of Collepino, for superb views over the entire valley.

Elevation

At Assisi - loop ride to Sta Maria degli Angeli or Collepino elevation profile

Day 8 · —Leave Assisi

Leave Assisi

Extending your holiday

Exterior of the Hotel Canada Roma

Hotel Canada Roma

Rome

  • Air conditioning
  • American Express
  • ATM
  • Bank
  • Hairdryers
  • Market
  • Mastercard
  • Safe
  • Shops
  • Tea & coffee

The 3 star Hotel Canada Roma is centrally located near the main railway station, making it an excellent base from which to explore Rome. Each room is ensuite and has been lovingly decorated in an elegant Italian style complete with vintage furniture. Rooms come with tea and coffee maker as well as air conditioning and safe.

This well appointed hotel also boasts a bar for pre dinner drinks and nibbles, as well as an external courtyard where you can savour a drink under the stars.

What our travellers say

The cycle routes were carefully and thoughtfully arranged to provide a beautiful day cycling every day of the holiday. Thank you.

Mr Bamford

Well organised, good contact during holiday(train strike in Italy) but the cycling app was excellent and liberating

A Valued Customer

Helpful agents, good hotels, well planned routes & a good guidance app.

Mrs Matthews

The navigation app for biking was excellent. Headwater was prompt and friendly in their responses with all trip planning.

A Valued Customer
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Positive impact

Carbon score for this trip

11.0

Kg CO₂e

per person, per night

Relative to other Headwater trips

We measure emissions from the parts of the holiday we organise — including accommodation, in-trip transport, meals and activities — and express them as CO₂e per person, per night. Our label doesn’t include your travel to and from the start of the trip. As a Certified B Corp, Headwater is committed to reducing this figure and to positively impacting local communities, the local environment and our staff. Learn more

From£1,219per person