We have improved our walking grade scale. Read more

Trails of Medieval Umbria

Europe Lates Offers Early Booking Offer

■ Location: Italy

■ Duration: 7 nights

■ Board Basis: Half Board

■ Travel Dates: Sep 2026, Jun-Sep 2027

■ Itineraries available: 1

■ Choice of Walking Grades: 5 & 7 details

■ Carbon Footprint: 653kg CO2 details

Non-members From

£1,929

pp

Inc flights

Members From

£1,879

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.
foto_Terrazza-3.jpg

Walking grades

From September 2026, we have expanded our walking grade scale from 6 to 10 points. While the holidays themselves have not changed (the routes, daily distances and ascent levels remain the same), our newly expanded 1-10 scale offers greater distinction between holidays and clearer grade descriptions, so you can choose a holiday that best suits you.

Moderate walking grade 5

Moderate walking grade 5

Some walking experience needed. Full day walks which may include some short but steep ascents and descents throughout the day, and varied terrain. Regular stops. Typically, 8-9 miles (13-15km) with around 1,300ft (400m) of ascent.
Moderate walking grade 7

Moderate walking grade 7

The most active moderate grade. Longer distances and short but steep ascents and descents possible throughout the day. Hill walking experience desirable. Typically, 11-12 miles (18-19km) with around 1,800ft (560m) of ascent.

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

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

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    [title] => Arrival Day
    [introduction] => 
    [description] => 

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

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

                      Array
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    [id] => 01kwy7qqvx4n4yxch6gj7ta2rv
    [title] => Assisi
    [introduction] => 
    [description] => 

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.

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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.

) [1] => Array ( [title] => Mount Subasio [content] =>

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. 

) ) ) )

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: 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.

Option 2 - 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. 

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    [id] => 01kwy7qqzdfh884qhd3kktjxn3
    [title] => Wine Country
    [introduction] => 
    [description] => 

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.

[S] => 3 [E] => 3 [B] => [L] => [D] => [content] => Array ( ) [shared] => Array ( [content] => Array ( [0] => Array ( [title] => Bevagna to Montefalco [content] =>

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.

) [1] => Array ( [title] => Bevagna Circular via Montefalco [content] =>

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.

 

) ) ) )

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.

 

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    [id] => 01kwy7qr2whk1wbevfxkwq1pcs
    [title] => Free Day
    [introduction] => 
    [description] => 

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.

[S] => 4 [E] => 4 [B] => [L] => [D] => [content] => Array ( ) [shared] => Array ( [content] => Array ( ) ) )

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.

                      Array
(
    [id] => 01kwy7qr5690p9jtmkacbqdy1m
    [title] => Assisi to Spello
    [introduction] => 
    [description] => 

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

[S] => 5 [E] => 5 [B] => [L] => [D] => [content] => Array ( ) [shared] => Array ( [content] => Array ( [0] => Array ( [title] => Higher Route to Assisi [content] =>

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.

) [1] => Array ( [title] => Lower Route to Assisi [content] =>

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.

) ) ) )

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: 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.

Option 2 - 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.

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    [id] => 01kwy7qr7e8093hk792a0d1vng
    [title] => Spoleto and Monteluco
    [introduction] => 
    [description] => 

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

[S] => 6 [E] => 6 [B] => [L] => [D] => [content] => Array ( ) [shared] => Array ( [content] => Array ( [0] => Array ( [title] => Monteluco and the Bridge of Towers [content] =>

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. 

) [1] => Array ( [title] => Monteluco and the St Francis Way [content] =>

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.

) ) ) )

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: 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. 

Option 2 - 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.

                      Array
(
    [id] => 01kwy7qr9xrxtzwa820mvwkyy4
    [title] => The Aqueduct Ring Walk
    [introduction] => 
    [description] => 

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.

[S] => 7 [E] => 7 [B] => [L] => [D] => [content] => Array ( ) [shared] => Array ( [content] => Array ( [0] => Array ( [title] => Collepino and Foothills of Subasio [content] =>

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.

) [1] => Array ( [title] => To Collepino and Back [content] =>

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.

) ) ) )

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: 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.

Option 2 - 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.

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    [id] => 01kwy7qrd7n8ftcxh24rjyr1hm
    [title] => Departure Day
    [introduction] => 
    [description] => 

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

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

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.

The BV Grand Hotel Assisi

The BV Grand Hotel Assisi is an elegant four-star hotel set on the slopes of Mount Subasio, enjoying panoramic views across Assisi and the beautiful Umbrian valley. Ideally located for exploring the region, the hotel combines modern comfort with the rich history, culture, and natural beauty.

The hotel offers 155 stylish guestrooms which feature Wi-Fi, minibar and digital safe. The hotel offers excellent leisure facilities including a spa* with heated indoor swimming pool, sauna, steam room, fitness area, and rooftop terrace. Dining is a highlight at the hotel's Giotto Restaurant, where traditional Umbrian cuisine and regional specialities are served alongside local wines.

There is a one-off charge of €8 per person for an amenity kit to access to the hotel pool which includes, towel, slippers and swim cap.

*Charges apply for spa services and are payable locally.

More Information

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.  

If you are booking on a land-only basis, you can join the group transfer at an additional cost. To do so, your arrival and departure times must be in line with the scheduled group flight timings. Guests travelling at different times will need to arrange their own transfers. Please contact us before booking to discuss the available options and costs.

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)  

  • Swimcap (compulsory in Itialian resorts)

  • 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)

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.

 

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

 

 

Travel insurance is a condition of booking. Therefore, if you have not already arranged insurance, it is imperative that you do so before you travel.

For more information about healthcare and its costs, please visit: https://www.nhs.uk/using-the-nhs/healthcare-abroad/

Drinking Water

Standards for drinking water vary widely around the world. In many destinations, tap water may not be safe to drink, brush your teeth with, or use for making ice. Where advised, you should drink only bottled or treated water and ensure that bottle seals are intact before use. If bottled water is unavailable, water should be boiled or filtered.

Staying well hydrated is particularly important in hot climates and during active holidays. Carry water with you and drink regularly. 

If you are unsure about local water safety, check official country-specific health advice before travel, or ask your accommodation or local guides for guidance once you arrive.

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.

Learn more

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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. Add HF Membership to your booking online. Read more about membership

2026

26 Sep - 3 Oct 2026

7 nights. Trip notes

2027

Early Booking Offer Save £50 Per Person

15 Jun - 22 Jun 2027

7 nights. Trip notes

Twin & double rooms

Non-members

£1,999 £1,949

£1,829 £1,779

pp

Members

£1,949 £1,899

£1,779 £1,729

pp
Single rooms

£1,999 £1,949

pp

£1,949 £1,899

pp

£1,829 £1,779

pp

£1,779 £1,729

pp

Early Booking Offer Save £50 Per Person

14 Sep - 21 Sep 2027

7 nights. Trip notes

Twin & double rooms

Non-members

£2,149 £2,099

£1,929 £1,879

pp

Members

£2,099 £2,049

£1,879 £1,829

pp
Single rooms

£2,149 £2,099

pp

£2,099 £2,049

pp

£1,929 £1,879

pp

£1,879 £1,829

pp

Early Booking Offer Save £50 Per Person

21 Sep - 28 Sep 2027

7 nights. Trip notes

Twin & double rooms

Non-members

£2,099 £2,049

£1,899 £1,849

pp

Members

£2,049 £1,999

£1,849 £1,799

pp
Single rooms

£2,099 £2,049

pp

£2,049 £1,999

pp

£1,899 £1,849

pp

£1,849 £1,799

pp
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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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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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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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