Trails of Medieval Umbria

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7 nights accommodation

Availability Sep 2026

One itinerary available

Half Board

Grades 2 & 4 details

653kg CO2 details

Non-members From

£1,779

pp

Inc flights

Members From

£1,729

pp

Inc flights

For group booking of 10 or more please click here
Nicknamed the “green heart of Italy” for good reason, Umbria rewards with stunning landscapes, deep green valleys, cloud-shrouded mountains, and plentiful Roman and Etruscan towns that set the scene for some incredible walks. Highlights include our hotel location in Assisi within easy access of the Basilica of St Francis sampling wine in Montefalco, and admiring the Bridge of Towers - a colossal structure measuring over 236 metres long and some 80 metres high.

Accommodation

A range of handpicked hotels...
Surrounded by eye-pleasing views of the countryside and yet just 900m from the historic centre of Assisi, the Hotel La Terraza is an ideal base for exploring Umbria. Rooms are simple yet comfortable and come with all mod cons including Wi-Fi and air conditioning. As for facilities, the hotel boasts an outdoor swimming pool, a spacious restaurant serving local food and wine, and a full spa - perfect for indulging in post-walk relaxation or a treatment.
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What You’ll Love

  • Discovering Assisi, birthplace of St Francis
  • Getting a taste for Umbrian wine in Montefalco
  • Walking through vineyards, olive groves, and woodlands
  • Climbing to the treeline of Mount Subasio, known as the holy mountain
  • Admiring the Bridge of Towers, a feat of engineering
  • Staying at a traditional, family run hotel just minutes from the centre of Assisi

What's Included

  • Return flights from London Heathrow, including baggage and transfers
  • A choice of 2 guided walks per day with local leaders (on walking days)
  • HF Holidays Tour Manager
  • 7 nights' accommodation in Assisi
  • 7 breakfasts & 7 dinners (2026)
  • All in-destination transport

Reviews


Itinerary

All our carefully-curated itineraries are designed by our experts. While we make every effort to adhere to the described itinerary, we may take alternative routes or adapt the running order for weather and/or operational reasons.

Itinerary

Transfer to your hotel. Welcome drink and meeting followed by dinner.

Our first full day is an introduction to the postcard-pretty town of Assisi. We’ll follow in the footsteps of St Francis and explore the footpaths of Mount Subasio - Italy's so-called holy mountain.

Option 1 - Mount Subasio

Distance: 8.9 miles (14.4km)

Ascent: 2,585ft (788m)

Descent: 157ft (48m)

Today's harder walk takes us into the foothills of Monte Subasio, known as the holy mountain. The scenery changes as you go from town to forest to meadows, full of flowers in spring. After taking in the views from the treeline, we descend on a different path back into the town. 

Option 2 - The Forest of St Francis

Distance: 7.5 miles (12km)

Ascent: 1,070ft (326m)

Descent: 1,083ft (330m)

Leaving the hotel, we'll head into the town of Assisi and then the woods of St Francis, following the ancient rocky path at the foot of impressive Basilica of St Francis.

Starting in the walled medieval town of Bevagna, we'll set off through the vineyards to Umbria's wine capital, Montefalco - most famous for its Sagrantino red wine.

Option 1 - Bevagna to Montefalco

Distance: 5 miles (8km)

Ascent: 1,352ft (412m)

Descent: 157ft (48m)

Take some time to explore Bevagna before following a series of tracks through olive groves and criss-crossing the vineyards for views of the valley. We’ll climb into the medieval walled town of Montefalco, where you'll get time to explore this beautiful town known as the balcony of Umbria, and of course the chance to buy and taste its famous wines.

Option 2 - Bevagna Circular via Montefalco

Distance: 11 miles (17.6km)

Ascent: 1,352ft (412m)

Descent: 1,358ft (414m)

After discovering Bevagna, we’ll climb out of town to follow a ridge passing through vineyards, tiny hamlets, and pretty chapels whilst taking in the views. Rest up in Montefalco, where you can sample a glass of local wine at one of the cafes before setting off on a lower trail through the vineyards back to Bevagna.

 

Each week there is a free day when no guided walks are offered. This is an ideal opportunity to relax around the hotel, walk independently, or visit local places of interest. Options include:

Spello

You could easily spend the day enjoying Spello. Explore its warren of medieval streets and visit the church of Santa Maria Maggiore to admire frescoes painted by Pinturicchio, Umbria’s most famous artist.

Perugia

Alternatively, take the train to the region’s capital, Perugia, and head up to the hilltop viewpoint - on a clear day you can see Lake Trasimeno. Explore the subterranean Etruscan temple and wander the traffic-free streets to Piazza V Novembre with its gothic cathedral and impressive fountain.

This morning our walks depart directly from the hotel and follow the St Francis Way on Monte Subasio to the town of Spello.

Option 1 - Higher Route to Assisi

Distance: 8.2 miles (13.2km)

Ascent: 2,165ft (660m)

Descent: 2,790ft (850m)

This is our hardest option of the week but certainly worth the effort. As you climb the foothills of Monte Subasio the views over the Umbra Valley are jaw-dropping. We'll pass by the ornate Abbey of San Benedetto before dropping down into Spello.

Option 2 - Lower Route to Assisi

Distance: 7.5 miles (12km)

Ascent: 735ft (224m)

Descent: 1,329ft (403m)

Leaving Assisi, we stick to the lower trail of the St Francis Way along Monte Subasio where there are fantastic views over the Umbra Valley. Making our way through vineyards and olive groves to Spello, we’ll eventually pass behind Villa Fidelia – a grand Baroque manor complete with exotic gardens and expansive grounds.

The ancient hillside town of Spoleto is our destination today and a chance to explore this lovely town with two different walking options.

Option 1 - Monteluco and the St Francis Way

Distance: 9.5 miles (15.3km)

Ascent: 1,332 ft (406m)

Descent: 1, 175ft (358m)

Heading south out of Spoleto, we pick up the old railway line running between Spoleto and Norcia and climb steeply through the Sacred Wood of Monteluco, following the St Francis Way to Monteluco and Le Aie. We’ll walk through dense forests overlooking glittering rivers before making our descent back into Spoleto.

Option 2 - Monteluco and the Bridge of Towers

Distance: 4.5 miles (7.2km)

Ascent: 682ft (208m)

Descent: 732ft (223m)

Our route follows the Via dei Condetti of Monteluco with lovely views of the town of Spoleto. There is free time afterwards to enjoy the cathedral , Roman amphitheatre, archaeological museum, the castle, art museum, and admire the Bridge of Towers. 

We visit the hilltop town of Spello today with its narrow winding alleys and ancient sandstone houses. We’ll pass the impressive Porta Montanara to climb above Spello into the olive groves for views of Monte Subasio and the Vale of Spoleto.

Option 1 - Collepino and Foothills of Subasio

Distance: 8.2 miles (13.2km)

Ascent: 1,565ft (477m)

Descent: 1,660ft (506m)

Following the same route as option one to the village of Collepino, you then climb to circle Monte Pietrolungo passing through olive orchards, before taking the Olive Trail back into Spello.

Option 2 - To Collepino and Back

Distance: 7.3 miles (11.8km) 

Ascent: 1,089ft (332m)

Descent: 1,181ft (360m) 

After passing the Porta Montanara, we follow the ancient aqueduct trailthat fed water to the town. Admire the views across the valley as you walk through olive-laden fields and onto the pretty village of Collepino. From here you head downhill following a section of the Olive Trail to Spello.

It’s the final day – we’ll depart for Rome Airport, which is about a three-hour drive away. 

Daily Walk Options

Grade 2

Easier Walks

Good paths but walks are a bit longer. Some walks, particularly in mountain areas, may have sections over rough or steeper terrain.

Grade 4

Medium Walks

Long distances in remote countryside and on rough terrain. You can expect some sustained ascents and descents; there may be occasional sections of scree and steep ground.

Accommodation

Hotel La Terrazza

Surrounded by eye-pleasing views of the countryside and yet just 900m from the historic centre of Assisi, the Hotel La Terraza is an ideal base for exploring Umbria. Rooms are simple yet comfortable and come with all mod cons including Wi-Fi and air conditioning. As for facilities, the hotel boasts an outdoor swimming pool, a spacious restaurant serving local food and wine, and a full spa - perfect for indulging in post-walk relaxation or a treatment.

Sogno di Davide Country House - 13th June 2026 only

Sogno di Davide Country House is an elegant countryside retreat less than a mile from Assisi's historic centre, offering a blend of wellness, nature, and refined comfort. This boutique escape features a panoramic spa, an infinity pool overlooking Umbria, and thoughtfully designed rooms equipped with modern comforts like free Wi‑Fi, minibar, kettle, safe, flat‑screen TV, and air conditioning.

More Information

Vaccinations & health information EU NEW 2026

Before booking, you should check with your doctor to see whether any health precautions are needed for your trip. Health advice and requirements can change, so we recommend doing this in good time before travel.

As a general rule, travellers should ensure they are up to date with routine UK vaccinations and boosters, including, for example, MMR and diphtheria, tetanus and polio. Some countries may require you to have specific vaccinations such as Malaria, Rabies and Yellow Fever. Please check with your GP if you are unsure.

Please note that the use or possession of some common prescription or over-the-counter medicines is restricted or banned in certain countries. If you will be carrying medication, you should check with the relevant embassy or consulate before travelling. As an extra precaution, we recommend keeping medication in its original packaging, carrying a copy of your prescription, and, where possible, asking your pharmacist to provide the medication name in the language of the country you are visiting.

For further country-specific health advice, visit www.fitfortravel.nhs.uk or www.traveldoctor.co.uk. If you are travelling from outside the UK, please consult your own doctor and check local entry requirements.

 

Passport & Visa information - SHARED FOR ALL EU NEW 2026

This information is for those travelling with a full ‘British Citizen’ passport; for all other nationalities or passport holders, please check with your local consulate for advice.

Passport Requirements

This information applies to travellers holding a full British Citizen passport. Entry requirements vary by destination and can change at short notice. For most EU and worldwide destinations, passports must be valid for the entire duration of your stay. Some countries also require a minimum period of validity remaining on your passport (often up to 6 months beyond your return date), even if you are not staying that long.
We strongly recommend ensuring your passport has at least six months’ validity remaining at the time of travel to avoid any issues.

If you hold a different type of British passport or a passport issued by another country, you must check the requirements with the relevant embassy, consulate, or official government website.

Visa Requirements

Visa rules depend on your nationality, destination, length of stay, and purpose of travel, and they can change frequently. It is your responsibility to check whether you require a visa before travelling.
British passport holders should check the latest entry, passport validity and visa requirements for their destination on the UK government’s Foreign, Commonwealth & Development Office (FCDO) website:
https://www.gov.uk/foreign-travel-advice

 

 

Packing list - Overseas Guided Walking

It's best to be prepared for all weather conditions. To make it easier, here is a list of items you should consider packing.   

Essentials  

  • Walking boots 
  • Waterproof jacket 
  • Waterproof trousers 
  • Insulated jacket/top 
  • Walking clothing  
  • Walking socks (plus spares)  
  • Sunhat 
  • Gloves/mitts and warm hat
  • Water bottle (minimum 2 litre capacity)  
  • Headtorch 
  • High-factor sunscreen (minimum SPF 30)  
  • Sunglasses with a dark lens 
  • Rucksack (15-30 litres)  
  • Mobile phone 
  • Personal first aid kit (containing your medication, blister plasters, etc.) 
  • Passport 
  • Visa (if applicable) 
  • Copy of your travel insurance policy 
  • UK Global Health Insurance Card (formerly known as EHIC

Recommended

  • Collapsible walking poles 
  • Swimwear and travel towel
  • Snacks
  • Dry bags
  • Rubbish bags
  • Insect repellent

Optional extras

  • Camera 
  • Sit mat
  • Flask for hot drinks 
  • Durable lunch box
  • Gaiters 
  • GPS device (excluding Bhutan, Georgia and India)

With flights EU & WW

Book your holiday ‘with flights’ and you can choose to depart from a range of UK airports* to your destination. For latest flight times and prices please call us on 0203-974-8865 or email reservations@hfholidays.co.uk  

If you choose to book your flights with us, we automatically include return transfers between the destination airport and hotel.  

Without flights EU

Alternatively, tailor your journey to suit you by booking your holiday ‘without flights’ and you’ll have the freedom to book your own flights from your local airport.   

*Subject to availability 

Carbon Footprint - 653kg CO2

We see it as our responsibility to minimise our emissions, not just for this year but every year to come. Our work with sustainability experts, ecollective, has enabled us to measure our carbon footprint and create a strategy to reduce the carbon intensity of our product by 5% each year. Our ambition is to be net zero by 2040 – earlier if we can.

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Reviews

Code: UBM07-LCL09

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Dates & availability

Trails of Medieval Umbria

Members save an additional £50 on this booking and get a range of other exclusive benefits. You can join during booking process. Read more about membership

2026

5 Sep - 12 Sep 2026

7 nights. Trip notes

Call to Enquire

19 Sep - 26 Sep 2026

7 nights. Trip notes

Call to Enquire

Save £150 Per Person

26 Sep - 3 Oct 2026

7 nights. Trip notes

Twin & double rooms

Non-members

£1,929 £1,779

£1,749 £1,599

pp

Members

£1,879 £1,729

£1,699 £1,549

pp
Single rooms

£2,214 £2,064

pp

£2,164 £2,014

pp

£2,034 £1,884

pp

£1,984 £1,834

pp
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Trusted British co-operative

We are proud to be Britain’s only walking holiday co-operative. Led by almost 40,000 members, offering hundreds of holidays across the UK and overseas, with all surplus being reinvested back into our Society.

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Flexible choice of guided walks

Experienced volunteer HF Leaders guide every walk at our UK country houses, offering up to three daily options. Making it easy to find a holiday to suit your ability, and with the flexibility to switch grades each walking day.

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Book early with confidence

Become an HF Member to benefit from our Price Pledge. Secure your first choice of holiday early, and if the cost drops after you book, we will automatically refund the difference (exc. travel agent & group bookings).

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Book with confidence

If the flights we have organised are cancelled or changed, we’ll do everything we can to find alternative transport, with minimal disruption to your holiday

If we cancel your holiday, we honour all refund requests 

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Travel with confidence

We know that peace of mind is priceless, so we’ll always go above and beyond to meet – and exceed – expectations

If the flights we have organised are cancelled or changed, we’ll do everything we can to find alternative transport, with minimal disruption to your holiday

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HF Holidays

A British heritage brand with 111 years of experience

Offering a choice of over 260 itineraries in nearly 40 countries

Run as a co-operative with 40,000-plus members

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