Welcome to the Big Smoke! England’s capital is a historical masterpiece – filled with pages of characters wearing bejewelled gowns, soot-smudged aprons and crisp suits. We can only imagine the breadth of its story as we greet each other in our hotel and get to know each other over a welcome dinner. Wonder what British staple will be on the menu this evening... 

After having our morning cup of tea, we’ll step onto our luxury minicoach for the first time. Chartwell House is our destination. You’ve probably heard of its owner, a certain Sir Winston Churchill, notably known for his famous address to British citizens, but what will you learn of his home habits? Peek at his library collection and eye his ‘Romeo Y Julieta’ cigar collection, imagining the swirls of smoke blanketing his study. Look out for Jock VII – the current resident ginger cat! Since the house opened to the public in 1966, the Churchill family requested ‘a marmalade cat named Jock... [would always be] in comfortable residence at Chartwell.’  

Our history lesson doesn’t stop there for the day. Next is Hever Castle, Anne Boleyn’s childhood home. Glide your fingers through pink and white rose petals in the garden. Gaze at the rippling lake. And venture inside to discover the Tudor treasures that lie within the castle walls. Two objects to find are Anne’s prayer books, complete with her inscriptions and signature! Brains filled with facts, we’ll continue our journey to Canterbury where we have the evening to discover what lies within the crooked cobblestone alleyways ourselves. 

A lofty ceiling with criss-crossed beams. An oak-roofed Chapter House. A staggering gothic nave. These are just three pieces that make England’s first cathedral a sight to behold. We’ll be joined by a local guide who’ll take us through Canterbury Cathedral, sharing tales of its journey through time since it was founded in 597 by St Augustine.  

Afterward, we’ll travel through the Kent countryside where the sun ripples through pale green leaves of ancient trees and villages hum with friendly locals who treat each other like family. And our final stop for the day? It’s our accommodation for the next two nights: Leeds Castle. Our Signature Moment of the tour, we’ll rest our eyes in uniquely designed en-suite rooms settled within the royal gardens. But first – a group dinner will be served in the Castle View Restaurant. Meaty homemade pies and garlicky chicken glazed in honey may be artfully placed on your plates, created by in-house chefs who proudly use seasonal local ingredients. 

Satisfied with your taste of Leeds Castle so far? This morning, we’ll delve deeper into its history with a local guide who knows all its secrets including witchcraft accusations, glamorous parties and royal affairs. As those secrets are spilled, we’ll wander around the moat, look inside grand bedrooms and explore the servant’s quarters.  

Time for a beer tasting! We’re heading to the medieval market town of Faversham to visit Shepherd Neame Brewery. It reigns as Britain’s oldest brewer with its doors opening in 1698 by young entrepreneur Richard Marsh. We’ll learn about the expertise that goes into beer brewing, followed by a visit to the Old Brewery which now stands as home to former delivery vehicles, past pub signs and a recreated coopers’ workshop. Then – let the tasting begin! Sample four ales freshly brewed earlier in the week, tasting the sweet and bitter hops between each clink of glass.  

A pint should always be followed by a slow amble, don’t you think? Our next stop of the day is the place for it! Pebble beaches with tiny oyster shacks lining the shore as fishing boats bob in the water, Whitstable will provide us with the fresh, salty air England’s known for.  

We’ll swap Maidstone for a place where centuries of England’s past blend together to paint a pretty picture: the small Kentish town of Tenterden. Together, we’ll wander its paved paths, taking in its Tudor buildings, local shops and hanging floral arrangements as our Tour Leader shares a story or two about this surprising pocket of England.   

It’s wine o’clock! Nestled between green fields is our next stop: a vineyard that creates sparkling English wine. We’ll be greeted by our host, owner Graham, who’ll take us through the grounds, sharing his personal story at every turn. You might be introduced to a sheep or two alongside the 10,000 vines! Finally, we’ll taste not one, not two, but four wines, and nibble at platters of cheeses and meats. Let’s toast – to the journey we’ve had and the days ahead. 

Burrowed in the medieval town of Rye lies the spot where the Hawkhurst Gang, local smugglers met under the guise of night in the 1730s and 40s. Tonight, we’ll slumber there – in an inn filled with secret hideaways, creaking floors and cellars that date back to 1156 – how do you feel about ghosts? 

After snoozing in our low-ceilinged, cosy accommodation we’ll begin the day with a walking tour of Rye. Our Tour Leader will take us through the zigzags of cobblestone streets, passing by independent ice cream parlours, moss-covered homes and Lamb House – home to authors Henry James and E.F. Benson. 

Eyes widened by the beauty of Rye, we’ll step onto our minicoach which will weave its way along the shoreline. See who in your small group spots those famous white cliffs first, before we arrive at Dover Castle. Wander its dark medieval tunnels and watch out for the covert cannons every few paces. Climb the Medieval Great Tower to discover the riches of Henry II’s court – asking the property steward any questions you wish. And look out to the waters from its enormous height, imagining English ships sailing home after years at sea. 

Back in Rye, you’ll have ample time to saunter at your own pace, getting lost in the maze of narrow passageways and picking up local souvenirs to take home. Tonight, we’ll gather for our final group dinner, swapping our favourite moments over hearty dishes and a clink of glasses. 

We have one last stop to make before our adventure through Kent ends. Sissinghurst Castle and Gardens takes the floral crown for its fame among English gardens. Clusters of rosebushes in a walled garden that once grew vegetables. Iris ‘Black Taffeta’ in deep shades of plum threaded between campanula and sweet rocket. And dainty foxglove and daisies planted together in another ode to the designer of this spectacular creation, poet and writer Vita Sackville-West. We’ll have time to leisurely stroll the grounds before our return to London where we part ways with a newfound love for the garden of England.