The English Wine Route - Hiking
Country
England
Region
London
Theme
Limited Edition
6
Days
5
Nights
Accommodation
4* / 5*
Vineyards, chalk cliffs and storybook villages in England’s sunniest corner.
Fresh air, fine wine and landscapes that seem to roll on forever – this is the South Downs. Together, we have shaped a journey that blends gentle walking with behind the scenes vineyard access, historic market towns and coastlines carved in chalk and salt. From woodland trails and award winning English sparkling wine to medieval streets and big sky coastal paths, each day flows ease. Consider this a walking holiday with a sommelier’s knowledge and a local guides planning.
Highlights
- Guided woodland walks linking vineyards and villages
- Private tours and tastings at pioneering English wine estates
- Coastal walking along the Seven Sisters and Cuckmere Haven
- Exploration of key market towns and villages – Lewes, Rye and Alfriston
- Carefully chosen spa hotels and characterful country inns
Handpicked Accommodation
The Star, Alfriston
A refined village inn at the heart of Alfriston, blending historic character with quietly confident design. Think crackling fires, polished wood and rooms that feel both classic and contemporary.
Why we chose it
Alfriston is one of the South Downs’ most charming villages, and The Star places you right at the region’s heart. From here, some of the area’s finest walks begin at the front door.
Ockenden Manor, Cuckfield
An Elizabethan manor house turned country spa hotel, set above the village of Cuckfield with views across rolling Sussex countryside. Inside, calm interiors and one of the region’s most inviting spa facilities are the highlights.
Why we chose it
Its location is ideal for vineyard hopping and woodland walking, and the spa offers the perfect retreat after an active day. Somewhere that encourages you to take things at slower pace.
Tillingham Winery, Tillingham
A working winery with striking modern rooms, set among the vines overlooking the rolling landscapes of East Sussex. Food and wine are very much at the centre of the experience.
Why we chose it
Sleeping amongst the vines brings the wine story full circle.
Itinerary
Day 1 – Woodland paths and a first sip of Sussex wine
Arrive at Haywards Heath station this morning and meet your guide, who is already thinking three steps ahead. A short transfer brings you to Ockenden Manor, where there is time to settle in and change before setting out on foot. The afternoon unfolds on a woodland hike through classic Sussex scenery, birdsong overhead and dappled light underfoot, leading you to Bolney Wine Estate. Here, a late lunch and tasting introduce the character and confidence of English wine. Return to the hotel for unhurried spa time, followed by dinner at the manor.
Day 2 – Across the Downs
After breakfast, we transfer to Artelium in Street for a guided tour and tasting that explores the estate’s artistic and sustainable approach to winemaking. From here, boots on again for a gentle two mile walk to Ridgeview Wine Estate. Lunch is taken amongst the vines, with wide views across the South Downs and a glass of something crisp. This afternoon, we visit the village of Ditchling and its acclaimed Museum of Arts and Crafts, a quiet celebration of design, movement and making. Return to Ockenden Manor for free time before dinner this evening in a welcoming local pub with easy conversation and good food.
Day 3 – Market Towns of Sussex
We head east this morning to Lewes, one of Sussex’s most characterful towns. Spend time exploring its medieval castle, strolling the cobbled high street and browsing independent antique shops. Lunch is taken in a cosy local coffee shop before we continue to Alfriston, set neatly in the Cuckmere Valley. This afternoon’s walk leads out to the Long Man of Wilmington, the mysterious chalk figure etched into the hillside. We finish with a pint of the Long Man’s eponymous beer at the brewery tap before checking in at The Star.
Day 4 – Fresh coastal air
An easygoing walk begins the day, tracing the meanders of Cuckmere Haven, a tidal estuary known for its birdlife and expansive views. As the path reaches the pebble beach, the scene opens wide and we turn towards the chalk cliffs of the Seven Sisters, bright and bold against the sea. After a hearty lunch, we take a short drive to Rathfinny Wine Estate for a tour and tasting that showcases one of England’s flagship sparkling wine producers. Return to Alfriston for a relaxed evening at your own pace.
Day 5 – Beachy Head Lighthouse and a fairwell feast
We head east today, pausing briefly at Beachy Head Lighthouse where land and sea meet in dramatic fashion. Onward to the historic town of Rye, where crooked houses and ancient streets tell tales of smugglers and sailors. Explore with your guide before enjoying a light lunch. This afternoon brings us to Tillingham Vineyards, where past, present and future of English wine come together. A guided tour leads into a generous farewell feast, paired naturally with wines from the surrounding vines.
Day 6 – Until next time
After a final night amongst the vines, we transfer you to Hastings station this morning and say farewell.
Itinerary Designer
This journey is about rhythm. Walk, taste, pause, repeat. Sussex rewards those who move through it slowly, and we have tuned every day to that pace.
Harvey
Featured Experience
Walking the Seven Sisters from Cuckmere Haven
Few walks in England can top this! Starting from the winding estuary of Cuckmere Haven and rising onto the chalk cliffs of the Seven Sisters.