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Wonders of Wessex

Highlights

Visiting several exceptional historic sites such as Salisbury Cathedral, Stonehenge, Wilton House and Wardour Castle

Beautiful English landscape of chalk downland and valleys in the Cranborne Chase and West Wiltshire Area of Outstanding Natural Beauty

A unique and engaging walk that follows quiet paths to link the highlights of this part of southern Wessex

Historic and picturesque settlements such as Shaftesbury with quaint thatched cottages

Reasonably gentle walking following ancient routes through timeless landscapes, along valleys and ridge tops on the Wiltshire / Dorset border

Holiday Profile : 5-7 nights, 4-6 days independent walking between guest houses. Option of extra nights in Salisbury at the start of your Wessex walking holiday

Dates : Everyday of the week subject to availability from 1 April to 31 October

At a Glance

A self-guided walking holiday exploring the beautiful Wessex countryside of southern England

Price

From € 743 per person

Every journey is tailor-made and can be personalised to your travel style, preferred accommodation and budget.

All highlights

Wonders of Wessex, Southern England

This self guided walking holiday in southern England explores the beautiful countryside of the Wiltshire / Dorset border in the heart of the ancient kingdom of Wessex. This historic and pre-historic landscape is made up of rolling chalk hills and secluded valleys and includes Cranborne Chase, a former medieval, royal hunting estate. Your walk starts in the historic city of Salisbury with its cathedral, a masterpiece of early English architecture, boasting the highest spire in the UK; and finishes at Shaftesbury, a Saxon hilltop town with stunning views, lovely historic cottages and of course, the stunningly beautiful street of Gold Hill. In between, your walking trail follows secluded valley meadows with babbling streams and idyllic villages, as well as following ancient Wessex routes on rolling chalk downland offering marvellous far-reaching views.

Each day you’ll have a variety of interesting sites and experiences, as your walking trail meanders through some of the finest landscapes in southern England in the Wiltshire and Dorset hills. The most famous site is without doubt, the prehistoric stones at Stonehenge, which is at the centre of the densest complex of Neolithic and Bronze Age monuments in England, including several hundred burial mounds. Your walking holiday also passes through rich wildlife areas such as ancient forests, which in Spring are carpeted in bluebells and protected chalk downs with orchids. You’ll also have the chance to visit the lovely house and grounds of Wilton House, the historic sites of Old Sarum and Wardour Castle, as well as several charming villages such as Ashmore and Tollard Royal

Accommodation & Meals

This independent walking holiday includes 5 – 7 nights B&B in a variety of small quality guest houses with ensuite accommodation. Mixture of inns or pubs, bed & breakfasts and small hotels. They are located in delightful historic properties, mainly in villages, but some in beautiful locations in the countryside. The B&B’s are generally 4 star AA rated. Lunches are picnic meals, often provided by your guest house. Evening meals are taken in local pubs and restaurants.

Navigation, Walking Notes & Maps

This walking holiday for the most part follows clear paths, tracks and minor roads. Some sections follow recognised long-distance walking trails which are clearly signposted, whilst others follow local trails which are less well signed and less frequently used. Although we have selected the best trails in any specific area, some can be muddy or unclear for short sections, so it is important to carefully follow the walking instructions. Our walking notes are very detailed and include intermediate distances for sections of the trail. They also include information about the sites which can be explored along the route. We supply one walking guide per person on this holiday.

At a Glance

Moderate

A moderate walking holiday with each day's walk averaging 17km or 10 miles with moderate ascents of about 120m at a time, with maximum daily ascent being 400m. The walk follows many different types of paths, tracks and small country lanes. Occasionally the walking trail is steep when ascending or descending the chalk escarpments, but in general the walking is gentle in nature. At some points you need to be vigilant with route finding and follow the walking notes closely because not all of the trails are well-signed. This walking holiday is graded moderate. You should have some experience of day walking and be in reasonable health. See more information about walking grades.

Itinerary

Day 1: Arrival in Salisbury

Welcome at your guest house in the beautiful cathedral city of Salisbury in Wiltshire. You may wish to arrive early in order to have more time to explore this lovely city and visit its amazing gothic cathedral which has the tallest spire in Britain. It also has beautiful cloisters and houses one of the remaining copies of the Magna Carter. Extra nights at Salisbury are possible at the start of your independent walking holiday.

Day 2: Salisbury - Amesbury

Today's walk starts by visiting the impressive earthworks and remains of Old Sarum. Located on a hill just outside of Salisbury, Old Sarum is the site of the ancient city of Salisbury before a new city was built on its present-day site in the 13th century. Afterwards, you'll follow the delightful and secluded Woodford Valley with its small quaint villages and manor houses and the clear waters of the river Avon flowing through it. You can stop off at one of the numerous inns en route for refreshment before making your way to the town of Amesbury and your lovely guest house.

5 night version of the walking holiday goes direct to Broad Chalk, whilst the 6-night version goes direct to Great Wishford

Overnight: Amesbury, Walk: 20km, +250m

Day 3: Amesbury - Great Wishford via Stonehenge

Today you'll have the chance to visit a collection of prehistoric sites which are unrivalled in Britain. Visit the world-famous Stonehenge with its enigmatic stones, as well as other sites such as Woodhenge close by and a plethora of other pre-historic mounds and earthworks. After walking across open downland you'll pass through the pretty village of Stapleford with its thatch cottages to reach the Wylye Valley.

Overnight: Great Wishford, Walk: 17-21km, +300m

Day 4: Great Wishford - Broad Chalk via Wilton

Your walking route starts by following a short section of the Monarch's Way (a long-distance trail which follows the route taken by Charles II after his defeat at the Battle of Worcester in 1651.) This path climbs onto a chalk down covered in an ancient forest at Grovely Wood; a great place to see carpets of bluebells in the Spring lighting up the forest floor. Your walking trail follows the edge of the chalk downs with great views of Salisbury Cathedral before descending to the pretty town of Wilton, the ancient capital of Wessex. You have the chance to visit the impressive Wilton House and its gardens, before crossing over the hills to reach the beautiful Ebble Valley in the Cranborne Chase - an ancient royal hunting estate.

Overnight: Broad Chalke, Walk: 17-22km, +300m - shorter option available

Day 5: Broad Chalke - Ludwell

The first half of today's walk follows the ancient ridge-top track (known as a drove) that linked Salisbury and Shaftesbury before modern roads. Beautiful views from the chalk escarpment across the Wessex countryside and numerous earthworks accompany your delightful walking trail. Afterwards, you'll descend from the chalk downland to reach the haunting ruins of old Wardour Castle, used in the film Robin Hood: Prince of Thieves. You'll then follow the Wessex Ridgeway trail through typical English Parkland with fine old trees and the secluded Nadder Valley to reach your accommodation at Ludwell. 16km, +300m

Overnight: Ludwell, Walk: 16km, +300m

Day 6: Ludwell - Farnham

Your walking trail climbs steadily onto the hills to reach Win Green, the highest point in this part of Wessex with stunning panoramic views which on clear days reach as far as the Isle of Wight in the English Channel and Glastonbury Tor. You'll follow a beautiful ridge top along an old Ox Drove before a gradual descent takes you to the pretty village of Tollard Royal hemmed in its valley bottom. Afterwards, you have the opportunity to visit Larmer Tree Gardens, before the short walk to your next guest house. 13-14km, +210m

Overnight: Farnham, Walk: 13-14km, +210m.

Day 7: Farnham - Shaftesbury

Your last day's walking takes you back up onto the hills via the pretty village of Ashmore. Lovely historic thatched cottages surround a large pond set on the chalk plateau. Your walking route will then take you to Melbury Beacon, a great local viewing point before heading to the historic hilltop town of Shaftesbury in Dorset. You'll enter the town by the famous Gold Hill with its steep cobbled street lined with thatched cottages. Explore this Saxon town, whose abbey was established by the daughter of Alfred the Great in 888. You'll be supplied with a walking route around the town to take in all of the best views from the escarpment surrounding Shaftesbury. 18km, +380m

Overnight: Shaftesbury, Walk: 18km, +380m.

Day 8: Departure from Shaftesbury

7-night holiday ends after breakfast.

Independent walking holiday from Salisbury to Shaftesbury through the beautiful landscapes of Dorset & Wiltshire in southern England

When to Travel

Our self-guided walking holiday in Wiltshire-Dorset is available from 1 April to the end of October. Rainfall in the south of England is below the UK average, with conditions generally drier on average in Salisbury than in Shaftesbury in the west. July has the lowest level of rainfall on average of any month, as well as the warmest temperatures. As some parts of the walk follow ridgetops and hills, you may be exposed to windy conditions, which may help to keep it fresher in warmer weather but may make it feel cold in poor weather. Here is more detail concerning the walking seasons.

Spring
The climate is generally mild in spring, especially from April onwards with a good number of sunny clear days, interspersed with cooler and wet weather. During April and May the average daytime temperatures are between 12°C and 17°C.

Summer
Most days in summer range from mild to warm with the possibility of some rare hotter days. There may be overcast and humid conditions in the summer and the risk of storms is highest in the summer. From June to August the average daytime temperatures are between 18°C and 22°C.

Autumn
The climate can vary from some pleasantly mild days particularly at the start of September to cooler days in October. Visitors can see some wonderful autumn colours in the gardens open to the public along the trail. From September to end of October the average daytime temperatures drop from 18°C to 14°C.

Extra Nights

Extra nights are possible at any of the stopovers during the holiday. If you wish to have more time to explore the historic city of Salisbury, then we would recommend an extra night so that you can meander the historic streets at your leisure, as well as having the time to walk around the meadows that surround the city. We would also recommend extra nights in Shaftesbury. William, the founder of High Point Holidays was born in Shaftesbury and grew up locally. He can recommend several walks or places to visit in the area.

Combining walking holidays

Our Wessex walking holiday can be combined with any of our walking holidays in southern England such as the Dorset Jurassic Coast, just an hour’s drive away.

Tailor-Made Trips

Here is a selection of tailor-made trips to inspire you when considering your next holiday in southern Britain.

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An Unforgettable Adventure Through the English Countryside

Imagine a 10-day English adventure packed with historic castles, charming villages, and a dose of that classic British charm. This trip has a bit of everything for everyone. Get ready for a down-to-earth exploration that’s all about enjoying England’s diverse landscapes and soaking in its unique culture. It’s going to be 10 days of awesome discoveries and shared experiences – the kind of trip that sticks with you long after you’ve unpacked your bags.