This 8-day Winchester to Eastbourne South Downs Way walk is the perfect choice if you’d like a little more time to explore places of interest en route, as well as the towns and villages you are staying in. There is one long day but generally, this itinerary will allow you to enjoy your surroundings and the stunning scenery along the route. This holiday is suitable for anyone with a decent level of fitness.
Check in to your accommodation then explore this beautiful, historic city.
• The cathedral city of Winchester.
• Beacon Hill – it’s a nature reserve and commands outstanding views of the surrounding countryside.
• Old Winchester hill – great views and there is a fine Iron Age hill-fort site at the top.
• Old Winchester hill – great views and there is a fine Iron Age hill-fort site at the top.
• Butser Hill – the highest point on the South Downs Way at 270 metres.
• Queen Elizabeth Country Park – large area of beautiful mixed woodland.
• Harting Down – fantastic views across the Weald, it’s possible to see the North Downs on a clear day.
• Heyshott Down – great views inland.
• Bignor Roman Villa – dating back to 3rd Century AD, with amazingly preserved mosaic floors. It’s 1.5 miles from the South Downs Way and just off the old Roman road Stane Street.
• Bignor Hill – fantastic views right along the Downs.
• Amberley Working Museum – excellent museum of local history, just off the way.
• Amberley village – one of the prettiest villages in the South Downs, just off the way.
• First views of the sea to the south.
• Views of Amberley Brooks nature reserve after climbing out of Houghton Bridge and Amberley.
• Chanctonbury Ring – said to be haunted, it’s the site of an Iron Age hill-fort dating back to the 6th Century BC. Fantastic views out to sea and along the downs.
• Bramber Castle – the remains of a Norman castle on the banks of the River Adur
• River Adur – views south towards the stunning hillside Abbey at Lancing College.
• Fulking Hill – spectacular 360 degree views.
• Devils’s Dyke – legend has it that the Devil dug the valley to drown the parishioners of the Weald..
• Jack & Jill Windmills – famous local landmarks that can be seen from miles around.
• Ditchling Beacon – heading east from here, there are fantastic views inland across the weald and towards the Ashdown forest.
• Lewes – this pretty county town is steeped in history
• Great views inland to the north and the sea to the south, particularly from Firle Beacon.
• The picture postcard village of Alfriston.
• Cuckmere Valley – where the river Cuckmere meanders it’s way to the sea
• Seven Sisters – iconic, glorious coastal scenery, arguably the highlight of the whole South Downs Way
• Beachy Head – spectacular chalk cliff jutting into the English channel with fine views west across the Seven Sisters and east over Eastbourne and beyond.
The spectacular Seven Sisters make a fitting finale to the South Downs Way. You can then either depart Eastbourne in the afternoon or stay over and depart the following day, giving you a chance to explore this elegant seaside resort or just put your feet up!
£830 per person for 8 nights.
£880 per person for 9 nights (overnighting in Eastbourne at the end of your walk).
These prices are based on two people sharing, single supplement of £40/night applies. This walk is available to book any time between 24 May – 31 October 21.
We understand that good quality accommodation is the key component to a successful walking holiday and often the difference between a good holiday and a great one! So rest assured, after a long day’s walking you can expect a very warm welcome. We don’t like leaving anything to chance, so we personally visit all our accommodation providers, as well as constantly monitoring customer feedback and online reviews. We know all our B&B owners very well and we only work with nice people! Here’s just a small selection of some of the handpicked B&Bs, hotels and country inns we use – feel free to check them out on Tripadvisor, we do!
Magdalen House, Winchester – situated close to the city centre and very handy for the start of the trail, Magdalen House is a friendly, welcoming B&B and a great base to explore Winchester from.
Black Hole B&B, Winchester – this quirky, characterful B&B is highly rated and promises a unique experience. It’s also perfectly situated being close to the start of the trail as well as the city centre.
The Long House, East Meon – situated in a peaceful, rural location, the Long House is a barn and stable conversion offering very comfortable accommodation
The Village Inn, Buriton – situated in a peaceful location in the picturesque village of Buriton, the Village Inn is a privately owned pub and hotel offering very comfortable accommodation.
Moonlight Cottage & The Malthouse, Cocking – first class B&B accommodation in a characterful farmhouse and charming flint and brick cottage
Guillards Oak, Midhurst – Conveniently situated in a quiet location yet close to the town centre, Guillards Oak is a welcoming B&B offering comfortable accommodation.
Arun Valley B&B, Houghton Farm, Houghton – a working farm with two good pubs nearby, Houghton Farm is a welcoming B&B with very comfortable accommodation
Two Farm Cottages, Amberley – located in the picture perfect village of Amberley and with fantastic views of the Downs, Two Farms Cottages is a very welcoming, high quality B&B
The Sportsman, Amberley – the Sportsman offers comfortable accommodation, very good food and drink and stunning views across Amberley Wildbrooks
Arden House, Arundel – situated in a quiet yet central part of historic Arundel, Arden House is a welcoming guesthouse with an excellent standard of accommodation
Hill View, Steyning – set in the picturesque village of Steyning, Hill View provides comfortable accommodation in a peaceful setting
Downs View, Upper Beeding – an outstanding, family run B&B offering extremely spacious and comfortable accommodation
Murrells B&B, Lewes – tucked away in a tranquil spot yet just 5 minutes from the centre of Lewes, Murrells is an excellent, friendly and welcoming B&B.
Deans Place Hotel, Alfriston – set on the banks of the Cuckmere River, Deans Place is an excellent hotel offering very comfortable accommodation and excellent amenities
Riverdale House, Alfriston – enjoying a peaceful setting with wonderful views, Riverdale House offers very comfortable accommodation
Southcroft Guesthouse, Eastbourne – conveniently located near the end of the South Downs Way, Southcroft Guesthouse provides a warm welcome and excellent accommodation
If you have the time to spare, we’d really recommend taking a day off during your walk. This not only gives your legs and feet a rest, but also gives you the opportunity to explore the local area, and there is plenty to see and do!
The historic town of Arundel, with its magnificent castle and cathedral, is well worth a visit, as is the historic county town of Lewes. Or you could just take a leisurely stroll around the beautiful village of Amberley, or just put your feet up for the day!
Arundel Castle
If you’d like to celebrate a special occasion while you’re away, or if you just fancy treating yourself for a night or two, we can arrange upgrades to some of the very best accommodation the South Downs has to offer. Here are just a couple of examples of some truly memorable places to stay:
Amberley Castle, Amberley
Wingrove House, Alfriston
Check in to your accommodation then explore this beautiful, historic city.
• The cathedral city of Winchester.
• Beacon Hill – it’s a nature reserve and commands outstanding views of the surrounding countryside.
• Old Winchester hill – great views and there is a fine Iron Age hill-fort site at the top.
• Old Winchester hill – great views and there is a fine Iron Age hill-fort site at the top.
• Butser Hill – the highest point on the South Downs Way at 270 metres.
• Queen Elizabeth Country Park – large area of beautiful mixed woodland.
• Harting Down – fantastic views across the Weald, it’s possible to see the North Downs on a clear day.
• Heyshott Down – great views inland.
• Bignor Roman Villa – dating back to 3rd Century AD, with amazingly preserved mosaic floors. It’s 1.5 miles from the South Downs Way and just off the old Roman road Stane Street.
• Bignor Hill – fantastic views right along the Downs.
• Amberley Working Museum – excellent museum of local history, just off the way.
• Amberley village – one of the prettiest villages in the South Downs, just off the way.
• First views of the sea to the south.
• Views of Amberley Brooks nature reserve after climbing out of Houghton Bridge and Amberley.
• Chanctonbury Ring – said to be haunted, it’s the site of an Iron Age hill-fort dating back to the 6th Century BC. Fantastic views out to sea and along the downs.
• Bramber Castle – the remains of a Norman castle on the banks of the River Adur
• River Adur – views south towards the stunning hillside Abbey at Lancing College.
• Fulking Hill – spectacular 360 degree views.
• Devils’s Dyke – legend has it that the Devil dug the valley to drown the parishioners of the Weald..
• Jack & Jill Windmills – famous local landmarks that can be seen from miles around.
• Ditchling Beacon – heading east from here, there are fantastic views inland across the weald and towards the Ashdown forest.
• Lewes – this pretty county town is steeped in history
• Great views inland to the north and the sea to the south, particularly from Firle Beacon.
• The picture postcard village of Alfriston.
• Cuckmere Valley – where the river Cuckmere meanders it’s way to the sea
• Seven Sisters – iconic, glorious coastal scenery, arguably the highlight of the whole South Downs Way
• Beachy Head – spectacular chalk cliff jutting into the English channel with fine views west across the Seven Sisters and east over Eastbourne and beyond.
The spectacular Seven Sisters make a fitting finale to the South Downs Way. You can then either depart Eastbourne in the afternoon or stay over and depart the following day, giving you a chance to explore this elegant seaside resort or just put your feet up!
£830 per person for 8 nights.
£880 per person for 9 nights (overnighting in Eastbourne at the end of your walk).
These prices are based on two people sharing, single supplement of £40/night applies. This walk is available to book any time between 24 May – 31 October 21.
We understand that good quality accommodation is the key component to a successful walking holiday and often the difference between a good holiday and a great one! So rest assured, after a long day’s walking you can expect a very warm welcome. We don’t like leaving anything to chance, so we personally visit all our accommodation providers, as well as constantly monitoring customer feedback and online reviews. We know all our B&B owners very well and we only work with nice people! Here’s just a small selection of some of the handpicked B&Bs, hotels and country inns we use – feel free to check them out on Tripadvisor, we do!
Magdalen House, Winchester – situated close to the city centre and very handy for the start of the trail, Magdalen House is a friendly, welcoming B&B and a great base to explore Winchester from.
Black Hole B&B, Winchester – this quirky, characterful B&B is highly rated and promises a unique experience. It’s also perfectly situated being close to the start of the trail as well as the city centre.
The Long House, East Meon – situated in a peaceful, rural location, the Long House is a barn and stable conversion offering very comfortable accommodation
The Village Inn, Buriton – situated in a peaceful location in the picturesque village of Buriton, the Village Inn is a privately owned pub and hotel offering very comfortable accommodation.
Moonlight Cottage & The Malthouse, Cocking – first class B&B accommodation in a characterful farmhouse and charming flint and brick cottage
Guillards Oak, Midhurst – Conveniently situated in a quiet location yet close to the town centre, Guillards Oak is a welcoming B&B offering comfortable accommodation.
Arun Valley B&B, Houghton Farm, Houghton – a working farm with two good pubs nearby, Houghton Farm is a welcoming B&B with very comfortable accommodation
Two Farm Cottages, Amberley – located in the picture perfect village of Amberley and with fantastic views of the Downs, Two Farms Cottages is a very welcoming, high quality B&B
The Sportsman, Amberley – the Sportsman offers comfortable accommodation, very good food and drink and stunning views across Amberley Wildbrooks
Arden House, Arundel – situated in a quiet yet central part of historic Arundel, Arden House is a welcoming guesthouse with an excellent standard of accommodation
Hill View, Steyning – set in the picturesque village of Steyning, Hill View provides comfortable accommodation in a peaceful setting
Downs View, Upper Beeding – an outstanding, family run B&B offering extremely spacious and comfortable accommodation
Murrells B&B, Lewes – tucked away in a tranquil spot yet just 5 minutes from the centre of Lewes, Murrells is an excellent, friendly and welcoming B&B.
Deans Place Hotel, Alfriston – set on the banks of the Cuckmere River, Deans Place is an excellent hotel offering very comfortable accommodation and excellent amenities
Riverdale House, Alfriston – enjoying a peaceful setting with wonderful views, Riverdale House offers very comfortable accommodation
Southcroft Guesthouse, Eastbourne – conveniently located near the end of the South Downs Way, Southcroft Guesthouse provides a warm welcome and excellent accommodation
If you have the time to spare, we’d really recommend taking a day off during your walk. This not only gives your legs and feet a rest, but also gives you the opportunity to explore the local area, and there is plenty to see and do!
The historic town of Arundel, with its magnificent castle and cathedral, is well worth a visit, as is the historic county town of Lewes. Or you could just take a leisurely stroll around the beautiful village of Amberley, or just put your feet up for the day!
Arundel Castle
If you’d like to celebrate a special occasion while you’re away, or if you just fancy treating yourself for a night or two, we can arrange upgrades to some of the very best accommodation the South Downs has to offer. Here are just a couple of examples of some truly memorable places to stay:
Amberley Castle, Amberley
Wingrove House, Alfriston
