Walking Holidays in Southern England

Picture a place of gentle hills and gorgeous stone villages. A place of honey coloured houses and luscious green meadows. A place of hedge lined country lanes. Picture this, and you have the Cotswolds. Our Cotswold Round is a circuit of some of the most picturesque towns and villages the Cotswolds has to offer. Their very names themselves an invitation to the inquisitive – Moreton-in-Marsh, Stow-on-the-Wold, Bourton-on-the-Water. Almost all of the round falls within the Cotswolds Area of Outstanding Natural Beauty. Covering over 2000 square kilometers, it’s the largest such protected area in England and Wales. Only Cheltenham lies outwith the boundary. On your journey you will walk through many nature reserves as well as Sites of Special Scientific Interest.

Cowslips carpet the grassland in spring and in summer look closely for the pyramidal orchid and bee orchid. Bluebell woods bring vibrant colour and sweet smelling lily of the valley fills air. The red kite and the skylark occupy the Cotswold sky. Rare butterflies flit from flower to flower and fortunate walkers may get to see a duke of burgundy or adonis blue. The ever present golden stone you’ll see is Oolitic limestone, formed sometime around 150-200 million years ago, when the Cotswolds were covered by a warm sea. Hundreds of Cotswold villages are built entirely of this stone. Consequently the Cotswolds have more protected or listed buildings than any other region. You may spot some Cotswold Lions, these shaggy sheep are bred in small numbers today, but were once the foundation of England’s wool trade with Europe. An industry amounting to almost 50% of the country’s economy. The magnificent churches you’ll see, many disproportionate in size to the villages they serve, were known as wool churches, constructed or enlarged by huge contributions from the wealthy wool merchants.

Accompanied by the sight of wildflowers and the sound of birdsong, this is a country walker’s dream. A mix of open meadow, track, woodland, river bank and country lane combine to make our 59 mile Cotswold Round a relaxing walk through what you’ll no doubt come to remember as quintessentially English countryside.

The Cotswold Way is a much-loved walk that stretches 102 miles from the medieval market town of Chipping Campden in the North Cotswolds to the historic City of Bath. Following the western edge of the Cotswold Hills, the trail journeys through gently rolling, sheep-grazed pastures, stunning beech woodland, and dreamy, honey-coloured villages built from the delightfully warm Cotswold stone.

You will cross ancient commons in an Area of Outstanding Natural Beauty, pass Neolithic burial barrows, beautiful stately homes, and historic battle sites. The path along the escarpment twists and turns, affording ever-changing views to the west towards the River Severn and the Malvern Hills.

Along the way, you’ll pass some of the Cotswolds’ most captivating historical sites. Sudeley Castle stands as a testament to the region’s royal past, while the ancient Belas Knap Long Barrow offers a direct connection to the Cotswolds’ Neolithic inhabitants. The Tyndale Monument, dedicated to the 16th-century scholar William Tyndale, commemorates his legacy and his role in making the Bible accessible to English speakers. Each of these sites, along with others scattered along the trail, ties the natural beauty of the area to centuries of human history and achievement.

The Cotswolds countryside is a haven for wildflowers, birds, and insects. In springtime, expect to see cowslips and hope to spot orchids. Carpets of bluebells colour the woodlands, sweet with the scent of lily of the valley. When walking through meadows, watch out for rare butterflies such as the Adonis Blue or the Duke of Burgundy, and high above you’ll spot the Skylark and the Red Kite.

If it all sounds like a scene from a picture postcard, then it’s because it is. Quite simply, it’s incredibly idyllic, it’s quintessentially English, and it’s an absolute delight to walk.

For those who love to stride out amid the fragrance of salty sea air and with the warmth of the sun on their face, the Isle of Wight Coastal Path is a dream come true.

Shaped like a diamond, the Isle of Wight really is a jewel in the English Channel, and our Coastal Path holidays are the perfect way to explore the island the Romans first named Vectis.

Our 72 mile circuit of the island begins in the seaport town of Cowes on the west bank of the River Medina. Cowes is home to the oldest and biggest sailing regatta in the world. From here we head south west to the historic town of Yarmouth, skirting Newtown National Nature Reserve as we go. Then it’s onwards to the village of Totland with its picturesque sandy beach, ahead of a breathtaking crossing of Headon Warren where you’ll catch your first glimpse of the iconic chalk stacks, The Needles, guarded by its lighthouse at the outer western end of the formation.

The grassy, whale backed ridge of Tennyson Down leads us east along the southern edge of the island, first past the chalk pebbled Freshwater Bay, then on to a collection of chines and home to one of the richest areas for dinosaur discovery in Europe. St Catherine’s Lighthouse marks the most southern point of the island and is one of the oldest lighthouse locations in Great Britain.

Shanklin, Sandown and Seaview continue the theme of sun, sea and sand. Ryde, home to the world’s oldest hovercraft operator, is now all that stands between you and the completion of your circuit.

The island has been home to Alfred Lord Tennyson, Charles Dickens, Charles Darwin and Queen Victoria. Also, thanks to Italian inventor Guglielmo Marconi, the birthplace of the radio. The Isle of Wight is also England’s largest island. Yet at high tide, becomes England’s smallest county!

Put simply, if you love the thought of walking round a beautiful and fascinating island, that enjoys more sunshine than some parts of Spain, then the Isle of Wight Coastal Path is most certainly the holiday for you.

The Peddars Way and the North Norfolk Coast Path combine to make a very accessible 93 mile walk, taking in the very best of the Norfolk countryside and coastline.

The Peddars Way is an ancient road dating back to the Bronze Age, which was later developed into a military route in Roman times and was later used by pilgrims during the 15th century. The 45 mile route is for the most part straight and relatively flat, following mostly green lanes and tracks, with some interesting archaeological sites along the way. Castle Acre priory and castle are worth a visit as well as the Bailey Gate, this dates back to 1200 and the road into the village still leads through the gate today.

The North Norfolk Coast Path follows the coastline for 45 miles from Hunstanton to Cromer, passing through Victorian seaside towns, charming fishing villages, beautiful beaches, and nature reserves with a wealth of birdlife. This easy-to-follow trail offers plenty to see, with fresh seafood stalls along the way enhancing its coastal charm. The Norfolk coast is perhaps a little less known than many parts of the northern coast and, as a result, remains quieter and more unspoilt, which only adds to its appeal.

These are by their very nature, one countryside and one coastline, two very differing landscapes, but what they share in common is that they are places of peace and tranquillity. Enjoy them as separate short breaks or combine them into one amazing adventure, either way you are guaranteed a truly memorable experience.

The South Downs Way starts at the ancient and historic city of Winchester and follows the northern crest of the chalk escarpment of the South Downs, all the way to the sea. Stretching for 100 miles through England’s newest National Park, to the seaside town of Eastbourne, this walking holiday offers a fabulous taste of this lovely rural area, with spectacular views, expansive fields, beautiful woodlands, picturesque villages and a good helping of history.

The South Downs Way is well marked and easy to follow. It is used by horse riders and cyclists, so is very accessible, with almost no stiles. It links many ancient and historic tracks, used by travellers and traders since the Stone Age. It is one of the easier National Trails, with few steep sections, apart from when the route drops down into river valleys, and for the descent to overnight stays in the pretty towns, villages and farms along the way.

Although seldom exceeding 250m (820ft), this walk gives a real sense of space and a feeling of being ‘on top of the world’. You’ll pass Iron Age hill forts, the spectacular chalk formations of The Devil’s Dyke and the Seven Sisters, as well as rolling countryside dotted with fields of grazing sheep, corn, and wildflowers. This journey offers a magnificent sense of solitude, centuries of history, and a cross-section of one of the most beautiful parts of southern England, with sweeping panoramas from Winchester’s historic streets to Eastbourne’s dramatic coastline.

The Thames Path National Trail follows the greatest river in England for 185 miles from its trickling source just outside Kemble in the rural Cotswolds to its vast presence at the Thames Barrier, just a few miles before it meets the sea.

The River, once vital to trade, helped grow England’s capital to the bustling city it is today. However, as railways and roads took over, this great trading route began to decline. In the 1930s, discussions began on how to revitalise the old Thames towpath, but it wasn’t until 1996 that the Thames Path officially became a National Trail. After years of work by groups such as the Ramblers Association and the River Thames Society, 16 miles of new towpath were added, completing the route.

Now, it’s a celebrated long-distance trail – well signposted and accessible, with only one brief incline beyond Goring Gap. Despite this small climb, the Thames Path remains suitable for walkers of all abilities, offering an easy, enjoyable experience overall.

As you walk, the river evolves from its gentle beginnings to its mighty flow through London. You’ll encounter tranquil water meadows, an abundance of wildlife and wildflowers, as well as quaint villages, historic market towns, and iconic locks. Watch herons poised at the water’s edge, and ducks and swans glide by. In lively towns like Marlow, Henley, and Eton, rowers and pleasure boats add to the river’s charm, while in the quieter rural stretches, a community of brightly painted canal boats moves at its own unhurried pace.

Add rest days along the way to explore local sights, from the famous spires of Oxford and the grandeur of Windsor Castle to the peaceful beauty of Kew Botanical Gardens.

The Ridgeway National Trail runs for 87 miles from Overton Hill near Avebury to Ivinghoe Beacon just north of Aldbury. The entire length of the trail lies within two Areas of Outstanding Natural Beauty – the North Wessex Downs and the Chiltern Hills, and passes through no fewer than five of the greenest counties in England – Wiltshire, Oxfordshire, Berkshire, Buckinghamshire and Hertfordshire. The trail also visits a number of National Nature Reserves, home to a vast array of birdlife, butterflies and wildflowers.

With a history dating back some 5,000 years, The Ridgeway is the oldest road in Britain, perhaps even in Europe. A way for prehistoric man to travel across the land on higher and naturally drier ground. For thousands of years it was a drove road, used for the transportation of livestock and goods. From their elevated position travellers would benefit from the relative safety of being able to see any dangers around them. Today, it’s a place of leisure, where walkers, cyclists and horse riders can exercise and enjoy the stunning scenery on offer.

The North Wessex Downs and the Chiltern Hills offer two quite differing landscapes and walking experiences, yet remain really quite complementary. From the World Heritage Site at Avebury, the trail travels north east along the chalk downs with the reward of fine views stretching into the distance and the pleasure of walking on broad, springy grassland. The Ridgeway drops down to cross the River Thames at Goring before climbing into the Chiltern Hills. This a more diverse landscape of open downland, chalk escarpment, farmland and woodland, utilising a variety of footpaths, bridleways and tracks.

The Ridgeway isn’t simply a long distance walking trail, it’s a historic monument too, dating back to the Neolithic Age. Some of the earliest archaeological remains to be found on the trail include Avebury Castle and the long barrows at Wayland’s Smithy and West Kennett. The Iron Age brought impressive Hill Forts with Barbury, Segsbury and Pulpit Hill among those visited on the trail. Grim’s Ditch likely dates from this period too. There are many chalk carvings on the downs, the most famous of these, the Uffington White Horse, dating back 3,000 years to the Bronze Age.

Step back in time and follow those who for five millennia have worshiped upon and walked The Ridgeway.