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Wilderness Walking

Highlights of Southern England

Next Trip: 10th - 19th May 2024 Duration: 10 Days / 9 Nights

From £3,845 View Prices & Dates

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Trip created by Anna Brownlow
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Region: The Cotswolds;New Forest;South Downs;Dorset
Trip Type: Wilderness Walking
Accommodation: Luxury
Max Group Size: 8
Deposit From: £961.25 £961.25


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All you need to know about your trip, this essential document is a must for all adventures.

Download Itinerary

In the company of a highly knowledgeable guide, join us on a wonderful walking holiday that winds through the jewels of southern England.

Experience the charming nature of the Cotswolds. The region is cherished for its pastoral charm and romantic, rural villages of caramel-coloured stone. Hike in the New Forest, a national park where the ancient rights of common pasture are still upheld. Donkeys, cattle, sheep and ponies roam freely across the countryside. Later, spend time among the chalk hills of the South Downs. Atlantic breakers wash clean and clear on powdery sand, and seabirds take to the wing on a breeze bright with salt and sunshine.

Traversing landscapes rich in history, visit ancient stone circles, fascinating museums, and Gothic castles. Eat lunch in wholesome cafes and picnic among old stone walls and grassy meadows. As the sky turns inky and thick with stars, soak up the warm glow of English hospitality as you dine, drink and relax in boutique hotels. Each location is unique in location, charm and character.

Trip Highlights

  • Enjoy hiking with your knowledgeable guide in the pastoral beauty of the southern England.
  • Visit the famous Needles Chalk Stack on the charming Isle of Wight.
  • Stay in handpicked accommodation, enjoying locally-sourced, seasonal food.

Day by Day Itinerary

Day 1 – Welcome to the Cotswolds

Meet your Wilderness Guide at Windsor and Eton Riverside Station this morning. After being relieved of your luggage, join your lovely guide for a walking tour of Windsor. Afterwards, have lunch at a cosy cafe before travelling west into the Cotswolds, an Area of Outstanding Natural Beauty (AONB). Arrive in Burford, an incredibly picturesque town with a stunning high street that sweeps down to the River Windrush. After settling into your delightful accommodation, head out for a stroll through the pretty streets and stop to visit the sharp-spired historic church. Enjoy a delicious dinner this evening in the warm ambience of your characterful hotel. (L, D)

Day 2 – A Classic Cotswold Walk

After breakfast this morning, head out for a wonderful day of walking in the Cotswolds. Accompanied by your guide, meander your way through the idyllic countryside and past Chedworth Roman Villa – one of the grandest Roman villas in Britain. Tucked beneath old trees, explore the stunning mosaic floors, heating systems and bathhouse rooms. After lunch, continue to Bibury and walk over to Arlington Row, a charming row of cottages built in 1380 as a monastic wool store. Enjoy pottering around, popping into some artisanal shops full of local produce and having a coffee before returning to your hotel for dinner. (B, L, D)

Walk details: 7 km/4.5 miles | 250 m/820 ft ascent | approx. 3 hours

Day 3 – Stonehenge and the Cerne Abbas Giant

As the warm sunshine slides across the fields, enjoy a morning visit to Stonehenge – the largest stone circle in Britain. An iconic, prehistoric monument, its evocative and fascinating nature is undeniable. Enjoy walking around with your guide learning about what we know, and, interestingly, what we don’t know about one of the world’s most famous places. Afterwards, continue to the charming village of Cerne Abbas, heading out after lunch for a walk to see the village giant – a 180 ft chalk figure carved into the sloping hillside. This evening, a short, scenic drive will take you to Lulworth Cove and your relaxed seaside hotel. (B, L, D)

Walk details: 9 km/6.5 miles | 290 m/950 ft ascent | approx. 4 hours

Day 4 – Fossil Hunting and the Isle of Purbeck

Wake to the smell of the sea and, after breakfast, head straight out into the salt-flecked air for a short morning walk. Wind your way along the Jurassic coast as it reveals stunning views of a gorgeous sandy beach and the striking limestone arch of Durdle Door. Returning to your hotel, hop in with your guide and drive to Kimmeridge to enjoy another fantastic hike which further explores this spectacular part of the coastline. Enjoy a private fossil hunting experience this afternoon, discovering evidence of life that existed millions of years ago. Afterwards, with fossils in hand, travel back to Lulworth Cove and enjoy a free evening. (B, L)

Walk details: 9 km/6.5 miles | 230 m/750 ft ascent | approx. 4 hours

Day 5 – Hiking in the New Forest

Leaving the rhythmic noise of breaking waves behind this morning, travel into the beautiful bounds of the New Forest National Park. Join your guide for a lovely hike, strolling beneath the boughs of ancient English oaks, looking out for wildflowers and making your way to the Huff Duff – an octagonal brick building used as a direction-finding station during World War Two. Chat with your guide about the interesting history of the area and relish the breathtaking views from Ibsley Common. Meander your way back down through the pine woodlands and, after lunch, enjoy a stroll around Blackwater Arboretum, which is home to a fantastic collection of trees from around the world. (B, L, D)

Walk details: 7 km/4.5 miles | 105 m/330 ft ascent | approx. 3 hours

Day 6 – The Isle of Wight

Take the ferry from Lymington to the Isle of Wight this morning, an island known for its stunning coastal scenery, verdant fields and open chalk hills. On arrival, drive to Osborne House, the historic home of Queen Victoria and gain an intimate glimpse into royal life. Enjoy a relaxed cafe lunch in the sunshine, soaking up the holiday atmosphere and chatting with your fellow travellers. This afternoon, visit the famous Needles Chalk Stack: walking out to the striking limestone cliffs and taking a chairlift up the sides of Alum Bay. Later, sail back to the mainland and enjoy dinner at your charming hotel. (B, L, D)

Walk details: 4 km/2.5 miles | 150 m/500 ft ascent | approx. 2 hours

Day 7 – Fishbourne Palace and Arundel Castle

After a good night’s sleep, travel east into the South Downs National Park. Along the way, visit Fishbourne Palace, the largest Roman home in Britain. Enjoy wandering through the airy museum, observing the intricate mosaics and visiting the stunning, recreated gardens. Afterwards, join your guide on a trail that winds its way through a protected wetland area and finishes at the restored medieval castle of Arundel. Admire the castle’s gothic architecture, preserved interiors and rare collection of paintings. From Arundel, continue your journey east, arriving in Midhurst and checking into one of England’s oldest coaching inns. (B, L, D)

Walk details: 7.5 km/4.5 miles | 135 m/440 ft ascent | approx. 3 hours

Day 8 – Hiking in the South Downs

After breakfast in the light-filled conservatory, lace up your boots and sling on your packs for an engaging hike with your guide. An excellent way to explore the scenic beauty of the Downs, the walking trail provides breathtaking views of the surrounding hills and valleys. Along the way, pass through the 12th-century St Margaret’s Church and the ancient crossroads at Ditchling Beacon. Upon your return, enjoy lunch at a 1930s English tea room and then a short drive takes us to visit the Long Man of Wilmington on Windover Hill. Check into your hotel in Alfriston this evening, and enjoy time to relax before dinner. (B, L, D)

Walk details: 8 km/5 miles | 290 m/950 ft ascent | approx. 3-5 hours

Day 9 – The Seven Sisters and a Wine Tour

After fresh coffee, enjoy a cracking walk to the chalk cliffs of the Seven Sisters. From a pebbly beach where the sea breaks turquoise on the shore, join your guide on a stunning coastal walk. Soak up the spectacular views as you wind your way along a headland sprinkled with wildflowers, making your way to Beachy Head – Britain’s highest chalk cliff. After lunch, as the sea glitters in the sunshine, transfer to Rathfinny Wine Estate and enjoy a private tour and tasting. Perfectly located, this award-winning vineyard produces some of the finest English sparkling wines in the country. Feeling warm-cheeked and merry, return to Alfriston this evening and enjoy dinner. (B, L, D)

Walk details: 10 km/6 miles | 475 m/1,560 ft ascent | approx. 5 hours

Day 10 – Ashdown Forest and Depart

As the morning blackbird sings brightly from a perch up high, head out with your guide for a walk that ribbons its way through Ashdown Forest. Better known perhaps by its fictional name – Hundred Acre Wood, Ashdown Forest is where Winne the Pooh (the much-loved children’s book character created by English author A.A. Milne) and Christopher Robin (Milne’s son) grew up together. The woodland is a magical, peaceful place, best explored on foot. After your walk, enjoy a relaxed lunch in a nearby cafe, before transferring back to Windsor. Finish your trip at Windsor and Eton Riverside Station, wishing your guide and your lovely group goodbye and beginning your journey home. (B, L)

Walk details: 3.5 km/2 miles | 95 m/310 ft ascent | approx. 2 hours

Wilderness Walking
Highlights of Southern England

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Trip Dates & Prices

Trip Dates for 2024AvailabilityStatusPriceBook
10th May - 19th May 20248 place(s) leftUNCONFIRMED£3,845Book Now
2nd Aug - 11th Aug 20248 place(s) leftUNCONFIRMED£3,845Book Now
20th Sep - 29th Sep 20248 place(s) leftUNCONFIRMED£3,845Book Now

Trip Details

Accommodation Read More

On this trip, we stay in 5 luxurious hotels.

In the Cotswolds, we stay in The Lamb Inn in the historic market town of Burford for two nights, tucked away down a peaceful side street and full of character.

We spend two nights in Dorset in Lulworth Lodge, a relaxed coastal hotel, just a pebble’s skim from the famous Lulworth Cove.

In the New Forest, we stay a couple of nights in the Montagu Arms, an elegant country house in the picturesque village of Beaulieu.

We spend one night in The Spread Eagle in Midhurst, one of England’s oldest coaching inns, greeting guests since 1430, reputedly, including Queen Elizabeth I. The hotel has a swimming pool, so remember to bring your swimwear.

For the final two nights, we stay at The Star in Alfriston. Originally a religious hostel dating from 1345 and then a traditional coaching inn, it has been remodelled into a luxury boutique hotel, a fitting end to the holiday.

Single Rooms

There is no supplement charged to solo travellers. However, you will be required to share a room with another person of the same sex. If you request a double room for single occupancy, a supplement of £1,075 is charged.

Due to the nature of the accommodations we use, single supplements are limited and are allocated on a first-come, first-served basis.

Meals Read More

On this trip all meals are included from lunch on day 1 to lunch on day 10, except for dinner on day 4. Included dinners are three courses as standard.

Day 4 will be a free evening, your guide will recommend options for dinner that evening and will help you make any necessary reservations, and then they’ll take the evening off.

Inclusions Read More
  • 9 nights accommodation in welcoming luxurious hotels
  • All meals during the trip, from lunch on Day 1 to lunch on Day 10, except for dinner on Day 4. Meals included indicated as B=Breakfast, L=Lunch, D=Dinner.
  • The services of an experienced and knowledgeable guide/driver throughout
  • All transport throughout the trip, starting and finishing in Windsor.
  • Activities mentioned in the itinerary.
Trip Grading Read More

Green Graded 1-3

Green graded walking holidays are suitable for active travellers who are reasonably fit and enjoy moderate hikes. We walk at a comfortable pace and you can expect to be out for 5-6 hours a day. The terrain will be mostly good paths and hill trails but these can still be muddy and rough in places. Some hikes may involve an ascent up to a max of approx 1,500 feet / 450m. Distances will be typically 8-10km but there may be the odd slightly longer day. Daily hike details are available in the itinerary.

Travel Read More

You will be met by your Wilderness England Guide at Windsor and Eton Riverside Railway Station at 10:30am on Day 1 of your trip. Meet at the fixed seating by the railings which separate the platforms from the station concourse.

The trip will conclude at Windsor and Eton Riverside Railway Station at 4:00pm on the final day.

The station is served by regular direct trains from central London and is also close to London Heathrow Airport.

Photo Gallery

Make This Trip Private

Fancy this trip just for your group? Get together with family and friends spend quality time exploring wild places. A private trip allows you to benefit from all the features of the group departure, including hand-picked accommodation and expert local guides but with the advantage of the flexibility to tailor the days to your group. Make the trip more or less challenging depending on your experience or choose to add in some optional extras like castle or distillery visits depending on your interests. The price of a private trip will depend on the number of travellers in your group. Let us know your prefered departure date and we'll take care of the rest.

Speak to an Expert

Jane Gillies

Our friendly office team hail from across the world but share a passion for the outdoor and wild spaces of England. We are committed to providing you with the best customer service and are more than happy to chat through options and provide help and advice. Get in touch to find your perfect adventure.

Ask Jane a Question

Meet Your Guide

Difficulty Grades Explained

Green Graded Walking Holidays
Green graded walking holidays are suitable for active travellers who are reasonably fit and enjoy moderate hikes. We walk at a comfortable pace and you can expect to be out for 5-6 hours a day. The terrain will be mostly good paths and hill trails but these can still be muddy and rough in places. Some hikes may involve an ascent up to a max of approx 1,500 feet / 450m. Distances will be typically 8-10km but there may be the odd slightly longer day. Daily hike details are available in the itinerary.

Compare walking grades

Our holidays reviewed
in your own words

This trip was amazing, we got to see so much of the 5 countries in so little time. The sites and locations that were mapped out were perfect. A rest day in Dublin is the perfect city to explore and find good food. The guides were knowledgeable and thoughtful, and made the trip very easy, all we had to do was bike and show up to dinner! Absolutely awesome experience.

Daniel Patton
Road Cycling - The Five Countries
Reviewed on 29/08/2022

Rated 4.95 out of 5 based on 716 reviews

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