Trails of Medieval Umbria
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.
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, 5 packed lunches & 6 dinners
- All in-destination transport
Trip Notes
Easy to download as a PDF, our trip notes provide detailed information for every holiday. Please click below to find the trip notes for your departure date.
Gallery
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.
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 - The Forest of St Francis
Distance: 7.5 miles (12km)
Ascent/Descent: + 1,070ft (326m)/- 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.
Option 2 - Mount Subasio
Distance: 8.9 miles (14.4km)
Ascent/Descent: 2,585ft (788m)/-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.
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/Descent: + 1,352ft (412m)/- 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)/- 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. There’s no dinner provided on this day so you could have a large lunch in Perugia or head to one of the many restaurants in Spello.
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 - Lower Route to Assisi
Distance: 7.5 miles (12km)
Ascent/Descent: + 735ft (224m)/- 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.
Option 2 - Higher Route to Assisi
Distance: 8.2 miles (13.2km)
Ascent/Descent: +2,165ft (660m)/-2,395ft (730m)
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.
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 Bridge of Towers
Distance: 4.5 miles (7.2km)
Ascent/Descent: + 682ft (208m)/ - 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.
Option 2 - Monteluco and the St Francis Way
Distance: 9.5 miles (15.3km)
Ascent/Descent: 1,332 ft (406m)/- 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.
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 - To Collepino and Back
Distance: 7.3 miles (11.8km)
Ascent/Descent: + 1,089ft (332m)/- 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.
Option 2 - Collepino and Foothills of Subasio
Distance: 8.2 miles (13.2km)
Ascent/Descent: + 1,565ft (477m)/- 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.
It’s the final day – we’ll depart for Rome Airport, which is about a three-hour drive away.
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.
Essential information
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
Guest reviews
All holidays are subject to availability. Supplements may apply.
Non-member fee: £30 per person.
If you choose land only, you will be responsible for making your own travel arrangements, including your flights and airport transfers at your destination. Any flights booked independently will also not be covered by our ATOL license.
Date (Start - End) | Itinerary | Double / Twin Room | Single Room | Notes / Offers | Trip Notes | Book | ||
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2025 | ||||||||
14 Jun - 21 Jun 2025 7 nights |
Itinerary Flight from London Heathrow Airport Single from £1,958 Double from £1,759 pp |
from £1,759 pp |
from £1,958 |
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02 Sep - 09 Sep 2025 7 nights |
Itinerary Flight from London Heathrow Airport Single from £1,978 £1,867 Double from £1,779 £1,668 pp |
from £1,779 £1,668 pp |
from £1,978 £1,867 |
Save £111 pp Birthday Offer |
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09 Sep - 16 Sep 2025 7 nights |
Itinerary Flight from London Heathrow Airport Single from £1,978 £1,867 Double from £1,779 £1,668 pp |
from £1,779 £1,668 pp |
from £1,978 £1,867 |
Save £111 pp Birthday Offer |
Trip Notes
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23 Sep - 30 Sep 2025 7 nights |
Itinerary Flight from London Heathrow Airport Single from £1,958 £1,847 Double from £1,759 £1,648 pp |
from £1,759 £1,648 pp |
from £1,958 £1,847 |
Save £111 pp Birthday Offer |
Trip Notes
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Book Now |
Date (Start - End) | Itinerary | Double / Twin Room | Single Room | Notes / Offers | Trip Notes | Book | ||
---|---|---|---|---|---|---|---|---|
2025 | ||||||||
14 Jun - 21 Jun 2025 7 nights |
Itinerary Single from £1,778 Double from £1,579 pp |
from £1,579 pp |
from £1,778 |
Trip Notes
|
Book Now | |||
02 Sep - 09 Sep 2025 7 nights |
Itinerary Single from £1,778 £1,667 Double from £1,579 £1,468 pp |
from £1,579 £1,468 pp |
from £1,778 £1,667 |
Save £111 pp Birthday Offer |
Trip Notes
|
Book Now | ||
09 Sep - 16 Sep 2025 7 nights |
Itinerary Single from £1,778 £1,667 Double from £1,579 £1,468 pp |
from £1,579 £1,468 pp |
from £1,778 £1,667 |
Save £111 pp Birthday Offer |
Trip Notes
|
Book Now | ||
23 Sep - 30 Sep 2025 7 nights |
Itinerary Single from £1,778 £1,667 Double from £1,579 £1,468 pp |
from £1,579 £1,468 pp |
from £1,778 £1,667 |
Save £111 pp Birthday Offer |
Trip Notes
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Book Now |
Important information
- With flights holidays: Price includes return flights to Perugia Umbria International Airport or Rome Fiumicino International Airport, hold baggage and airport transfers
- Independent travellers can join our airport transfers from Perugia Umbria International Airport or Rome International Fiumcino Airport - please contact us for prices
*If you prefer to make your own travel arrangements, please ensure you’ve selected a land-only option before proceeding to book.
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