South East England | Castles, Countryside and Historic Towns

Discovering South East England

👤 Written by Handpicked Stays 🗓️ 20th August 2026, last updated 12th September 2026

Stretching around London and reaching from the historic cathedral city of Canterbury to the university streets of Oxford, South East England combines beautiful countryside, fascinating history, grand estates and some of England's most characterful towns.

For this guide, we're exploring Kent, Surrey, Berkshire, Buckinghamshire and Oxfordshire. These five counties offer an extraordinary variety of experiences, from medieval cities and royal castles to chalk hills, ancient woodlands, country gardens and vineyards.

The South East is also a region where town and countryside are unusually close together. You can spend a morning exploring a historic city, an afternoon walking through protected countryside and an evening enjoying dinner in a village pub or country town.

Whether you're planning a weekend escape, a longer road trip or a collection of day trips from London, South East England offers plenty of opportunities to discover somewhere new.

Kent – Castles, Coast and the Garden of England

Kent is often known as the Garden of England, and it is easy to see why. Orchards, vineyards, rolling countryside and historic towns fill the landscape, while castles, cathedral cities and a dramatic coastline provide plenty of reasons to explore.

Canterbury is one of the county's essential destinations. Its medieval streets and magnificent Canterbury Cathedral form the centrepiece of a city with more than a thousand years of history. The cathedral, St Augustine's Abbey and St Martin's Church together form a UNESCO World Heritage Site.

Kent is also famous for its castles. Leeds Castle rises from a moat surrounded by extensive parkland and gardens, while Hever Castle is a romantic medieval castle associated with Anne Boleyn, whose childhood home it became. Further east, Dover Castle has played an important role in England's coastal defences for centuries and occupies a dramatic position above the English Channel.

The county's seaside towns offer a different side of Kent. Whitstable is famous for its oysters, harbour and shingle beach, while Margate combines a traditional seaside setting with contemporary art and culture. Along the coast, the White Cliffs of Dover provide one of England's most recognisable landscapes.

Beyond the major attractions, Kent is filled with attractive villages, historic houses, orchards and vineyards. The countryside around Sevenoaks and the High Weald is particularly rewarding, with places such as Knole and Chartwell adding further layers of history.

Kent is therefore a county where history, landscape and the coast come together. It is equally suited to a cultural city break, a countryside weekend or a longer journey through southern England.

Surrey – Hills, Gardens and Country Escapes

Surrey is one of the greenest counties surrounding London, with extensive countryside, historic market towns and the protected landscapes of the Surrey Hills National Landscape.

The Surrey Hills stretch across a substantial part of the county, providing some of the South East's most attractive walking country. Box Hill, Leith Hill and Newlands Corner are among the best-known viewpoints, while the surrounding villages and woodland paths make the area ideal for slower exploration.

Guildford is one of Surrey's principal towns and has a long history, with the remains of Guildford Castle overlooking the town centre. Nearby Dorking provides a gateway to the Surrey Hills and the county's growing wine scene.

Surrey is particularly strong when it comes to gardens and historic estates. RHS Garden Wisley is one of the Royal Horticultural Society's flagship gardens, while Painshill is an outstanding example of an eighteenth-century landscape garden, complete with lake, grotto and architectural follies.

The county has also become an important destination for English wine. Around the Surrey Hills, vineyards such as Denbies Wine Estate offer visitors the opportunity to discover the growing English wine industry while enjoying views across the surrounding countryside.

Surrey's appeal lies partly in its accessibility. Within a relatively short distance of London, it is possible to exchange busy streets for woodland, rolling hills, country estates and quiet villages.

Berkshire – Royal Heritage and the River Thames

Berkshire combines royal history, riverside landscapes and attractive towns, making it one of the most accessible countryside destinations from London.

The county's most famous destination is undoubtedly Windsor. Dominated by Windsor Castle, one of the world's oldest and largest inhabited castles, the town has a strong royal connection and a wealth of historic streets, shops, restaurants and riverside walks.

Across the River Thames, Eton provides another historic setting, best known for Eton College and its attractive streets. The Thames itself creates opportunities for walking, boating and cycling, while the surrounding countryside provides a quieter contrast to the busy royal town.

Further west, Newbury offers a different side of Berkshire. The market town sits on the River Kennet and provides a useful base for exploring the surrounding countryside and nearby North Wessex Downs.

Berkshire also has a strong collection of historic houses and gardens. Basildon Park, surrounded by parkland near the Thames, is one of the county's notable country estates, while the wider area contains numerous villages, historic churches and rural landscapes.

For visitors interested in history, walking or simply escaping the city, Berkshire offers an appealing combination of royal heritage, river scenery and open countryside.

Buckinghamshire – Chiltern Hills and Hidden History

Buckinghamshire is a county of rolling countryside, wooded hills, historic estates and fascinating stories. Much of its landscape is shaped by the Chilterns National Landscape, which provides an extensive network of walking routes, villages and viewpoints.

Marlow is one of the county's most attractive riverside towns. Set beside the Thames, it combines Georgian buildings, independent shops, restaurants and a picturesque suspension bridge, while walks along the river and into the Chiltern Hills provide plenty of opportunities to enjoy the countryside.

For history enthusiasts, Bletchley Park is one of Buckinghamshire's most significant attractions. Once the wartime home of Britain's codebreaking efforts, it now tells the story of the people, technology and intelligence work that took place there during the Second World War.

Waddesdon Manor offers another very different experience. The impressive nineteenth-century manor house is surrounded by gardens and a large estate, creating a remarkable setting for exploring architecture, art and landscape.

Hughenden, near High Wycombe, was the country home of Victorian Prime Minister Benjamin Disraeli and is now a National Trust property. Together with the surrounding Chiltern countryside, it provides another opportunity to combine history with walking and outdoor exploration.

Buckinghamshire is particularly enjoyable for visitors who like to combine attractive countryside with substantial historic attractions. The Chilterns, Thames Valley and historic estates create plenty of possibilities for a relaxed weekend away.

Oxfordshire – Oxford, the Cotswolds and the Thames

Oxfordshire brings together one of England's most famous cities with beautiful countryside, historic market towns and some of the country's most impressive country estates.

At its heart is Oxford, a city whose university colleges, historic buildings and winding streets have shaped its identity for centuries. Visitors can explore the colleges, museums and libraries, walk beside the River Cherwell or Thames, or simply spend time discovering the city's historic centre.

Just north of Oxford, Blenheim Palace provides one of the county's great highlights. The UNESCO World Heritage Site is a masterpiece of Baroque architecture and the birthplace of Sir Winston Churchill, surrounded by extensive parkland and formal gardens.

West Oxfordshire reaches into the Cotswolds, where towns and villages such as Burford, Chipping Norton and Woodstock offer a more rural experience. The landscape here is characterised by rolling hills, stone-built villages and country lanes.

Along the River Thames, Henley-on-Thames is famous for its riverside setting and annual Royal Regatta, while Wallingford and Abingdon-on-Thames offer further opportunities to explore historic riverside towns.

Oxfordshire is therefore a county that works particularly well for a varied itinerary. You can combine the museums and architecture of Oxford with country-house visits, Cotswold villages and peaceful walks beside the Thames.

Historic Towns and Villages in the South East

One of the great pleasures of travelling through South East England is discovering the towns and villages between the major attractions.

In Kent, Canterbury provides centuries of history, while Whitstable, Sandwich and the villages around the High Weald offer very different experiences. Historic buildings, independent shops and traditional pubs make these places particularly enjoyable to explore on foot.

Surrey has its own collection of market towns and villages, including Dorking, Godalming and Farnham. Their proximity to the Surrey Hills makes it easy to combine a town visit with a walk through the countryside.

In Buckinghamshire, Marlow and Beaconsfield provide attractive town centres, while villages throughout the Chilterns offer quiet lanes, traditional buildings and countryside walks.

Oxfordshire has an especially rich collection of historic towns, from Burford and Woodstock to Henley-on-Thames, Wallingford and Abingdon-on-Thames. Berkshire similarly offers places such as Windsor, Eton and Newbury.

Rather than simply travelling between the headline attractions, allow time to stop in these smaller places. Often the combination of an independent café, historic street, local shop and nearby walking route is what makes a South East England journey memorable.

Castles, Country Houses and Gardens

Few parts of England offer such a concentration of castles, historic houses and landscaped gardens as the South East.

Kent alone provides an extraordinary collection, from Leeds Castle and Hever Castle to Dover Castle and the historic properties around Sevenoaks. Each offers a different glimpse into England's past, whether through royal history, medieval architecture or grand country estates.

In Surrey, gardens such as RHS Garden Wisley and Painshill demonstrate how landscape design became an important part of the country-house tradition. The county also has historic properties and gardens scattered throughout its countryside.

Berkshire and Buckinghamshire continue the theme with places such as Windsor Castle, Basildon Park, Waddesdon Manor and Hughenden.

Oxfordshire offers perhaps the most spectacular example in Blenheim Palace, where Baroque architecture, formal gardens and extensive landscaped parkland combine to create one of England's most impressive historic estates.

These places are more than individual attractions. Together they reveal how generations of royalty, politicians, landowners and designers have shaped the landscapes of South East England.

Walking, Cycling and the Great Outdoors

South East England is much more than historic houses and towns. Its protected landscapes and extensive countryside provide excellent opportunities for walking, cycling and outdoor adventures.

The Surrey Hills National Landscape is one of the region's most accessible walking destinations, with routes around Box Hill, Leith Hill and Newlands Corner offering woodland, open downland and wide-ranging views.

The Chilterns National Landscape provides another extensive area for outdoor exploration. Its chalk hills, beech woodlands, villages and footpaths are particularly rewarding in spring and autumn, while the Thames Valley adds opportunities for riverside walks and cycling.

Kent offers a mixture of countryside and coastal walking, from the North Downs and High Weald to the White Cliffs of Dover. The county's vineyards and orchards also create attractive rural landscapes for exploring at a slower pace.

Oxfordshire and Berkshire provide numerous routes through river valleys, farmland and historic landscapes. The Thames is a particularly useful thread for walkers and cyclists, connecting towns and villages while providing a peaceful alternative to the region's busier roads.

You do not need to plan a demanding hike to enjoy the South East. A short walk through woodland, a riverside stroll or a few miles along a country lane can provide an entirely different perspective on the region.

Food, Wine and Local Flavours

The South East has a strong food and drink culture, with local produce ranging from Kentish fruit and English wine to traditional country-pub food and ingredients from the surrounding farms.

Kent is particularly well known for its orchards, vineyards and local produce. The county is one of England's leading wine-producing areas, while towns such as Whitstable have long associations with seafood and oysters.

Surrey has developed a reputation for English wine, particularly around the Surrey Hills. Vineyards such as Denbies provide opportunities to learn more about the production of English sparkling and still wines while enjoying the surrounding countryside.

In the Chilterns, local produce, traditional pubs and independent food producers are an important part of the countryside experience. Market towns such as Marlow and villages throughout Buckinghamshire provide plenty of opportunities to stop for lunch or an evening meal.

Oxfordshire also has a strong food and drink identity, from traditional pubs and farm shops to local breweries and vineyards. The county's market towns and villages are ideal places to sample regional produce without having to look far from the main attractions.

Across the South East, food is closely connected to the landscape. Orchards, vineyards, farms and rivers all contribute to the character of the region, making local food and drink a natural part of exploring it.

Why Visit South East England?

Perhaps the greatest appeal of South East England is the combination of accessibility and variety. Within a relatively compact area, you can explore ancient cities, royal castles, medieval villages, rolling chalk hills and grand country estates.

You can spend a day discovering the history of Canterbury, walk through the Surrey Hills the next day, explore the wartime history of Bletchley Park and then finish the weekend beside the River Thames in Windsor or Henley.

There is also considerable variety within the landscapes themselves. Kent combines countryside and coastline, Surrey offers wooded hills and vineyards, Berkshire brings royal and riverside heritage, Buckinghamshire combines the Chilterns with remarkable historic estates, and Oxfordshire brings together Oxford, the Thames and the Cotswolds.

The region is particularly appealing for short breaks because so many destinations are within easy reach of London and each other. Yet once you leave the main roads and explore the smaller towns and countryside, it can feel surprisingly peaceful.

For history, architecture, food, walking, gardens or simply a change of scenery, South East England offers an impressive range of experiences.

Planning Your South East England Adventure

South East England works particularly well as a collection of shorter journeys. Rather than trying to see everything in one trip, you could choose a county or small group of destinations and explore them at a more relaxed pace.

A Kent itinerary could combine Canterbury, Whitstable and the county's historic castles, while a Surrey break might focus on the Surrey Hills, gardens and vineyards. Berkshire works well for a Thames and royal heritage escape, while Buckinghamshire combines the Chilterns with Bletchley Park, Waddesdon and attractive market towns.

In Oxfordshire, you can build a trip around Oxford before travelling into the surrounding countryside, visiting Blenheim Palace, exploring Cotswold villages or following the Thames towards Henley and Wallingford.

Public transport can make some destinations particularly accessible from London, while having a car gives you greater freedom to explore the smaller villages, estates and rural landscapes.

Whichever approach you choose, allow time for the places between the headline attractions. A country walk, a village pub, an independent shop or an unexpected view across the countryside can become one of the highlights of the trip.

Plan Your South East Escape Today

South East England offers a remarkable combination of history, countryside and culture. From the cathedral streets of Canterbury and the castles of Kent to the Surrey Hills, the royal heritage of Berkshire, the Chiltern countryside of Buckinghamshire and the historic city of Oxford, there is an extraordinary variety to discover.

The region is close enough to London for easy day trips, yet varied enough to reward longer stays. You can explore grand country houses and ancient monuments, walk through protected landscapes, discover riverside towns or simply slow down in one of the many villages scattered across the countryside.

Whether you are planning a weekend break, a road trip or a series of shorter escapes, South East England provides plenty of opportunities to explore somewhere new.

And if you want to continue your journey through southern England, our guides to the South Coast and South West England offer two very different ways to explore the landscapes beyond the South East.

From historic cities and royal castles to quiet country lanes and beautiful gardens, South East England is a region that rewards curiosity – and there is always another town, estate or stretch of countryside waiting to be discovered.