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HomeWinchester to Eastbourne Cycle (2 Days)

Winchester to Eastbourne Cycle (2 Days)

6 days
106 miles / 171 km


(Booking code SDW6)

This is ideal for anyone very short on time and looking for a real challenge. You’ll need to be fit as you’ll be averaging around 17 miles per day, with 4 long days (one of them very long!)

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Day one

Arrive in Winchester

Check in to your accommodation then explore this beautiful, historic city.

Day two

Winchester to East Meon – 17 miles / 27 kms


• 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.
• Meon Springs – beautiful spot where you can get refreshments and fill up your water bottles.

Day three

East Meon to Cocking – 18 miles / 29 kms


• Butser Hill – highest point on the South Downs Way at 270 metres.
• Queen Elizabeth Country Park – large area of beautiful mixed woodland.
• The picturesque village of Buriton ( half hour (in total) detour from the way).
• Harting Down – fantastic views across the Weald, it’s possible to see the North Downs on a clear day.

Day four

Cocking to Steyning – 23 miles / 37 kms


• 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 glimpse of the sea to the south and sweeping 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.

Day five

Steyning to Lewes – 19 miles / 30 kms


• 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.

Day six

Steyning to Lewes – 19 miles / 30 kms


• Ditchling Beacon – heading east from here, there are fantastic views inland across the weald and towards ashdown forest.
• Lewes – this pretty county town is steeped in history• Monk’s House, Rodmell – this was the home of Virginia Woolf, now owned by the National Trust and open to the public.
• Iford Hill – great views inland towards Mount Caburn to the north and the sea to the south.
• The picture postcard village of Alfriston.

Day seven

Alfriston – Eastbourne – 12 miles / 19 kms


• 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!

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£595 per person for 6 nights.

£640 per person for 7 nights (overnighting in Eastbourne at the end of your walk).

These prices are based on two people sharing a room, single supplement of £30/night applies.

This walk is available to book any time between 25 March – 13 October 19.

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 a selection of some of the handpicked B&Bs, hotels and country inns we use – feel free to check them out on Tripadvisor, we do!


Giffard House Hotel, Winchester – a friendly, family hotel that offers luxury accommodation

3 Worthy Lane, Winchester

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

Cocking B&B, South Downs Way

Moonlight Cottage & The Malthouse, Cocking – first class B&B accommodation in a characterful farmhouse and charming flint and brick cottage

Guillards Oak, Midhurst

The Swan Inn, Midhurst

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

Amberley B&B

The Thatched House, Amberley – situated in arguably the most picturesque village along the route, you’re assured a very warm welcome from Guy and Mary in their beautiful, characterful home (which despite the name is not thatched!)

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

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

Upper Beeding B&B

Downs View, Upper Beeding – an outstanding, family run B&B offering extremely spacious and comfortable accommodation


Murrells B&B, Lewes

South Downs Way hotel

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

The Star Inn, Alfriston – steeped in history and full of character, the Star Inn is a 13th Century Inn in the centre of Alfriston with a very good standard of accommodation

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

Optional Add-ons

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, South Downs Way walking holidays

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:

Luxury hotel Amberley

Amberley Castle, Amberley

Luxury hotel Alfriston

Wingrove House, Alfriston

Why book with us?

We love what we do!

We are passionate about the South Downs and are only too happy to share our knowledge and expertise to help you get the very most from your trip. Every walk we offer is one we have enjoyed ourselves!

South Downs Way experts

Our years of experience of working in, as well as walking and cycling throughout the South Downs National Park give us a level of expertise that’s hard to beat!

Perfect planning

We believe that attention to detail is the key to arranging the perfect walking holiday, so we take great care in planning your holiday to ensure everything runs like clockwork.

Flexibility and choice

Our friendly and flexible approach means that we can offer a genuinely tailor made service, and help you find the holiday that is perfect for you.

Handpicked accommodation

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!

Personalised service

We take great pride in ensuring that every single one of our customers receives outstanding service, specifically tailored to their needs. You’ll deal with the same person from your first enquiry until the end of your holiday, ensuring continuity and great service!

24/7 support

For your peace of mind, we provide you with a mobile number to contact us on should you need support outside office hours.

Responsible tourism

The natural beauty of the South Downs National Park is central to all our walking holidays, so we feel it’s important to play our part in protecting this beautiful area. We have a whole page on our website dedicated to responsible tourism and are also members of the South Downs Society, an independent charity dedicated to protecting the National Park for the enjoyment of future generations.

What’s included?

Handpicked accommodation

We only use a select range of accommodation providers which we personally visit and regularly review to ensure high standards.

En suite or private bathrooms

All rooms we book come with an en suite or private bathroom.


Breakfast is included in the price of your booking.

Reliable luggage transfer service

We work with South Downs Bag Transfers who will collect your bags each day after 0900 and drop off no later than 1600.

24/7 support during your holiday

For your peace of mind, we provide out of office hours support.

Guide book and map

We provide you with a Trailblazer guide book and a handy sized OS map booklet covering the whole route (one of each per booking).

Personalised trip notes

Our personalised trip notes include all our favourite lunch stops, points of interest along the route, directions to/from your accommodation and a guide to each town or village you stay in, including pub and restaurant recommendations.

Luggage labels

We will provide luggage labels to attach to your bags at the start of your trip.

Booking Form

Please complete the form below to book your holiday and we will respond to you within 48 hours.