Kent: The Garden of England

A capital filled with rich history and culture, London is where we'll meet for the start of our incredible journey. Tonight, we'll get to know one another over a delicious welcome dinner. Stay: Tower Suites by Blue Orchid (or similar) (D)

After breakfast, we'll set a course for our first historic stop: Chartwell House. Many of us will know the public face of Sir Winston Churchill, but a chance to see inside Chartwell will give us a glimpse into his private home. From the library to the sitting room and study, this red stone manor is a time capsule brimming with insights into 1930s family life. Next, we'll set our sights on the enchanting Hever Castle. We'll have the opportunity to wander through Anne Boleyn's childhood home and gaze upon the large collection of antique furniture, books and Tudor paintings housed here. Then, we'll move on to Canterbury – where we'll spend the evening at our leisure. Stay: Abode Hotel (or similar) (B)

Our day will begin with a locally guided visit to the magnificent Canterbury Cathedral. The oldest working church in England, this UNESCO World Heritage Site is home to medieval ruins, an oak-roofed Chapter House and a staggering gothic nave. Then: we'll move on to the picturesque Kent countryside – filled with quaint villages bursting with character. Tonight, we'll come together for a delicious included meal – sharing photos and stories of the day's adventures. Stay: Leeds Castle (or similar) (B/D)

This morning we'll take some time to explore Leeds Castle on a guided tour of the famous moat, the areas below stairs and the grand bedrooms (some of which were favoured by King Edward VIII and Wallis Simpson during their frequent stays). Then: onwards to the Shepherd Neame Brewery in Faversham, where we'll be treated to a tour – with the chance to sample some award-winning beers. We'll round off the day with a seaside stroll in the quaint town of Whitstable before returning to our idyllic accommodation for the evening. Stay: Leeds Castle (or similar) (B)

Next stop: historic Tenterden, a quintessentially English town overlooking the valley of the River Rother. After taking a wander around with our expert Tour Leader, we'll pull up a chair and get comfy at a local winery – where we'll clink glasses over an included wine tasting. Our final destination of the day will be the charming market town of Rye. Here, we'll spend the rest of the day at our leisure – with plenty of free time to visit the Rye Heritage Centre and explore the time-honoured town centre. Stay: The Mermaid Inn (or similar) (B)

Today we'll dedicate some time to exploring Rye's cobbled lanes and timber-clad houses, experiencing some of the magic that inspired writers and artists such as Henry James and Paul Nash. After tracing the shoreline and spotting those famous white cliffs, we'll arrive at Dover Castle: the gateway to the English coast.

This fortress boasts evocative interiors that tell centuries of historic tales, not to mention far-reaching views from the Great Tower and dark medieval tunnels with covert cannons every few paces. The afternoon will see us back in Rye, where some free time will allow for the chance to see more of the town before our farewell dinner. Stay: The Mermaid Inn (or similar) (B/D)

Our journey may be coming to a close, but we have one more stop before returning to London – the world-renowned Sissinghurst Castle and Gardens. Created by the poet and writer, Vita Sackville-West, this is one of the most famous gardens in England – featuring a particularly special collection of old garden roses. After enjoying some free time to stroll the colourful grounds, we'll make tracks back to London – where we'll say our goodbyes. (B)