• Kent
  • Sussex

From historic Canterbury to quaint Chiddingstone, explore castles, houses and charming villages

Personalised journeys from start to finish

Every trip helps support Conservation

Every detail taken care of

  • Personalised journeys from start to finish

  • Every trip helps support Conservation

  • Every detail taken care of

Suggested places to visit

What's included

  • Luxury accommodation throughout
  • Private transfers
  • Full support from your Travel Concierge before, during and after your trip
  • An expert local guide
  • Exclusive access to the Squerryes estate
Use this itinerary to inspire your bespoke journey

At a glance

Enter the dreamlike world of rural England and travel through the beautiful counties of Kent and Sussex as you experience life on country estates through the ages.

Begin your journey in Kent, the Garden of England. There is a concentration of beautiful castles nestled among the hills of this most picturesque of counties, from the Tudor pile of Hever Castle to the medieval Penshurst Place.

Travel further east to Canterbury and learn about this history of this centre of pilgrimage. Not far from the city is Provender, a charming manor house typical of the Kent style of architecture.

Prime Minister Winston Churchill was also a resident of Kent and after a visit to his former home, you’ll be welcomed onto a private estate and gain an insight into rural life in the 21st century. Nearby Goodwood is a thriving, modern estate and is best experienced by air, on an exhilarating flying experience.

You’ll the spend three days exploring Sussex. From here you’ll visit nearby Petworth which contains one of the most magnificent collection of paintings in any country house setting, as well as Hampshire, Jane Austen’s home turf. There is no better way to understand the life and times of this great author than by visiting her old haunts and the locations that inspired her novels. You’ll also enjoy a day discovering the vibrant city of Portsmouth, whose history goes back to the kings of France via the Mayflower and the D Day Landings.


Example trip itinerary

Days 1-5


Flights & transfers


Airside meet and greet at London Heathrow airport


Private transfer to your hotel in Kent

Accommodation in Kent

Five days exploring Kent Five days exploring Kent

With its lush countryside, manicured gardens and historic buildings, it’s no wonder this area is known as the Garden of England. Wander down picturesque, tree-lined lanes, explore old castles and charming villages.

Hever Castle Hever Castle

Hever Castle was the childhood home of Anne Boleyn and this picturesque castle contains many antiques and a collection of Tudor paintings. In the Edwardian period the castle was purchased by the American Astor family who brought it up to date and added the elegant Italian Garden.

* Visit the Tudor village of Chiddingstone * Visit the Tudor village of Chiddingstone

Tudor history comes alive at Chiddingstone village. This tiny village is a real time capsule and the half-timbered buildings lining the one and only street are one of the best preserved examples of their kind remaining today. The village is not a museum though and a church, primary school, cafe, pub and grocery store support a thriving local community.

Penshurst Place Penshurst Place

Penshurst Place is a romantic mediaeval pile with one of the best gardens in Kent. The house contains a fine collection of antiques collected by the Sidney family who have lived at Penshurst since the 16th century. The Elizabethan walled gardens cover 11 acres and have been divided into a series of rooms with displays that provide interest throughout the seasons.

Canterbury Cathedral Canterbury Cathedral

The venerable city of Canterbury is an ancient centre of pilgrimage and its cathedral is a focal point for the Anglican Church led by the Archbishop of Canterbury. Founded in 597, the cathedral was completely rebuilt between 1070 and 1077. The east end was greatly enlarged at the beginning of the 12th century and largely rebuilt in the Gothic style following a fire in 1174. It is one of the oldest and most famous Christian structures in England.

* Provender House * Provender House

Nestled in the Kent countryside not far from Canterbury is the intriguing Provender. This quaint country house is a beautiful example of Kent architecture and on a private tour you’ll learn about its connections with Jane Austen and the subsequent history of the house and how it was recently renovated from a near-derelict state.

Chartwell Chartwell

Visit Chartwell, the country home of Britain’s most famous Prime Minister, Winston Churchill. Chartwell was very much a family home and contains many personal objects which recount the history and lives of the Churchill family. The house was also a sanctuary for Sir Winston and today his studio contains the largest single collection of his paintings.

Wine estate Sussex
* Squerryes Country Estate * Squerryes Country Estate

The county of Kent is known as the Garden of England and is situated just to the south east of London. At Squerryes country estate, you’ll be welcomed by the owner and his family and enjoy the opportunity to learn about how an English country estate is managed in the 21st century. The house and grounds are usually closed to the public, but you’ll visit the elegant reception rooms with their wonderful collection of paintings, including many family portraits, and drive across the estate to view the vineyards where some of the best English sparkling wine is produced. You’ll have a chance to sample some of this wine at a private tasting hosted by the estate’s wine expert.

* Petworth House tour * Petworth House tour

Petworth House is a sprawling 18th century mansion now in the care of the National Trust. It contains one of the best collections of artwork in a country house setting in England, with priceless works by Titian, Bosch, Claude, Ruisdael, Teniers, Van Dyck, Lely, Kneller, Reynolds, Gainsborough, Blake and, most famously of all, landscape paintings by J. M. W. Turner, who was friends with the owner at the time and came to stay at Petworth and paint on numerous occasions.

* Fly over Goodwood Estate * Fly over Goodwood Estate

Visit the Duke of Richmond’s country seat at Goodwood. You’ll have time to visit the house and gardens with your guide but the best way of discovering the estate and the geography of the south coast is up in the air. Goodwood has its own private airstrip from which you’ll depart on an exhilarating flying experience.

Flights & transfers


Private transfer to your hotel in Sussex

Days 5-8


Accommodation in Sussex

Three days exploring Sussex Three days exploring Sussex

With a fascinating history, there’s plenty for Jane Austen enthusiasts to soak up over the next few days. Whether visiting coastal towns or stately homes with impressive art collections, a visit to Sussex is memorable.

* Discover Jane Austen’s Hampshire * Discover Jane Austen’s Hampshire

Many places lay claim to connections with Jane Austen, but there is no better way of understanding the life and times of the author than visiting her home ground in the county of Hampshire. You’ll spend the day with a specialist guide who will conduct you on a carefully crafted tour of some of the most important places featuring in Austen’s life and novels. From her father’s church at Steventon to her former home in Chawton, your visit will impart a new understanding of her work and influences.

Portsmouth Port
Day in Portsmouth Day in Portsmouth

Portsmouth packs a historical punch with a story that goes back to the kings of France via the Mayflower and the D-Day Landings. Its literary connections encompass Charles Dickens, Arthur Conan Doyle and Jane Austen and the last legally valid dual ever held in England took place in the city. Visit the Spinnaker Tower for panoramic views over Portsmouth and the Solent and discover naval history at the world-class Portsmouth Historic Dockyard.

Flights & transfers


Private transfer to your chosen London airport


Airside departure assistance

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Classic Country House Tour in Kent and Sussex

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