







Italy: Umbria
Average customer rating 5.0 / 5(4 verified reviews)
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.
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.
Our air-rail prices include standard flights, onward rail and station transfers.


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

Spoleto
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.

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

You stay at Albergo il Cacciatore

Spello
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.

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


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

You stay at Hotel Al Grappolo d’Oro

Torgiano
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.

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


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

You stay at Hotel Porta Nuova

Assisi
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.

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



Rome
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.
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