Kent

Chartwell was the cherished family home of Sir Winston Churchill, nestled in the hills near Westerham, Kent. He bought the property in 1922, drawn by the stunning views over the Weald. For over forty years, until shortly before he died in 1965, it served as his private sanctuary where he could write, paint, host guests, and escape the pressures of public life. After friends saved the estate for the nation and gave it to the National Trust, it opened to visitors in 1966.

The house remains much as the Churchills left it, packed with the books, maps, and personal belongings that bring Winston's world to life. In the garden studio, you'll find his largest collection of paintings, showing a more creative side of the man. Outside, guests can explore the grounds that inspired him, including the lakes he dug, the walls he built himself, and Clementine's rose garden, all surrounded by the beauty of the Kentish countryside.

Perched atop the famous white cliffs overlooking Dover, this massive English Heritage fortress has stood watch over England's gateway to Europe for nearly two thousand years. Inside, you'll find a Saxon church and the ruins of a Roman lighthouse, one of the oldest buildings in the country. At the center sits the Great Tower, built by Henry II in the late 1100s as a bold symbol of royal power, protected by layers of defensive walls.

You can tour the Great Tower to see its interiors brought back to life as Henry II's court, or stroll along the ramparts for incredible views of the Channel. The castle's real hidden gem is underground: a system of secret wartime tunnels that acted as the command center for the 1940 Dunkirk evacuation and later as a hospital. From medieval royalty to World War II, Dover Castle provides a fascinating glimpse into several different eras of British history.

Nestled in the Kent countryside, Hever Castle is a stunning double-moated estate famous for being the childhood home of Anne Boleyn, Henry VIII's tragic second wife and the mother of Elizabeth I. While parts of the castle date back to the thirteenth century, the Boleyn family later turned the fortified gatehouse into a cozy Tudor manor. This is where Henry VIII courted Anne, linking the castle forever to the drama of the English Reformation.

In the early 1900s, American millionaire William Waldorf Astor purchased Hever and spent a fortune restoring the building and designing lavish gardens. Today, guests can wander through Tudor rooms filled with antiques, portraits, and tapestries, including prayer books once used by Anne Boleyn. The 125 acres of grounds are a draw in their own right, featuring rose and Italian gardens, two mazes, and a lake, making it a great place to visit any time of year.

The Kent and East Sussex Railway is a charming heritage line stretching about ten and a half miles from the historic town of Tenterden in Kent to Bodiam in East Sussex, right by its famous moated castle. Originally built as a rural light railway by the pioneering engineer Colonel Holman F. Stephens, the line was designed to be cost-effective and is now carefully maintained by a dedicated team of volunteers.

Most trips are hauled by steam, though heritage diesels occasionally run, taking passengers through the beautiful scenery of the Rother valley, which is often called some of the best medieval countryside in north-west Europe. In Tenterden, the Colonel Stephens Railway Museum honors the man behind Britain's rural lines with exhibits on all sixteen of his projects. The trip is a great pairing with a visit to Bodiam Castle, and the railway keeps things lively with a full calendar of events, including steam galas, 1940s weekends, and festive Santa specials.

Perched on two islands in a wide lake near Maidstone, Kent, Leeds Castle is so stunning it's often called the most beautiful castle in the world. With a history stretching back to the Normans, it served as a home for several medieval English queens, earning it the name 'the ladies' castle'. Henry VIII later turned it into a palace for Catherine of Aragon, and in the 1900s, Lady Baillie meticulously restored and furnished the interiors.

Surrounded by vast parkland, the castle features opulent rooms and plenty to do outside. You can get lost in the yew maze and its hidden grotto, stroll through vibrant gardens, watch the birds on the moat, or check out the quirky dog collar museum. Between the falconry displays, the kids' play area, and the lakeside paths, it's a great spot for families and history buffs.

Located in the Kentish countryside near Tonbridge, Penshurst Place is one of England's finest surviving examples of 14th-century domestic architecture. Built in 1341 for Sir John de Pulteney, a wealthy London merchant and former Lord Mayor, its centerpiece is the Barons Hall—one of the largest and best-preserved medieval halls in the country, featuring a stunning chestnut roof. The Sidney family has called the estate home since 1552 and still owns it today.

Guests can wander through medieval state rooms filled with tapestries, portraits, and armor that chronicle the Sidney legacy, including that of the poet Sir Philip Sidney. Just as impressive are the eleven acres of walled Elizabethan gardens, where a mile of clipped yew hedges creates a series of outdoor "rooms" that bloom throughout the seasons. With its parkland, toy museum, nature trail, and adventure playground, Penshurst makes for a fantastic day out.

Tucked away in the wooded Weald of Kent near Tunbridge Wells, Scotney Castle is a National Trust site famous for being one of England's most romantic gardens. The center of the estate is a moated medieval ruin with sections dating back to the 1300s. In the 1830s, the owner Edward Hussey III built a new manor on the hill above, working with architect Anthony Salvin and designer William Sawrey Gilpin to intentionally turn the old castle into a picturesque centerpiece for the grounds.

The resulting gardens are stunning, especially when viewed from the Bastion, where the ruin is framed by trees and seasonal blossoms. Visitors can explore the quarry garden, the heather-thatched ice house, and the boathouse, or wander through the Victorian mansion, which remains much as it was for the family. To top it off, there are estate and woodland walks spanning over 780 acres.

Spanning eighty acres on Kent's River Medway, the Historic Dockyard Chatham sits on the site of a Royal Navy yard that spent four centuries building and repairing warships. For generations, shipwrights worked here, launching legendary vessels including Nelson's flagship, HMS Victory. Following the yard's closure in 1984, its impressive collection of Georgian and Victorian buildings, workshops, and slips were saved to create a maritime museum detailing the history of British naval power.

Visitors can explore three historic ships: the Victorian sloop HMS Gannet, the WWII destroyer HMS Cavalier, and the Cold War submarine HMS Ocelot, which was the final vessel built at the site. A standout feature is the quarter-mile Victorian Ropery, which still produces rope using traditional techniques on one of the UK's last working ropewalks. With its galleries, RNLI lifeboat collection, children's playground, and period streets often seen in movies and TV shows, it makes for a fascinating day out.

Located on the Kent coast near Deal, Walmer Castle was part of a series of artillery forts built by Henry VIII around 1539 to protect England from invasion. While its low, rounded bastions were originally meant for heavy cannons, the fortress eventually evolved into a cozy country home. Since the 1700s, it has been the official residence of the Lord Warden of the Cinque Ports, a prestigious role held by many notable figures.

The castle is most famous for its connection to the Duke of Wellington, who lived here for over twenty years and passed away on the grounds in 1852; guests can still see the chair he died in and a pair of his iconic boots. Now managed by English Heritage, Walmer is surrounded by over eight acres of stunning gardens, featuring flowering borders, a walled kitchen garden, woodland trails, and sculpted yew hedges that make it a wonderful place to wander.

The White Cliffs of Dover are some of England's most famous landmarks, where towering white chalk walls rise over the English Channel at the closest point to mainland Europe. For centuries, they have welcomed travelers arriving by sea and stood as a symbol of home and protection. Their legacy was cemented by wartime songs and their vital role in World War II, when the cliffs and port formed the front line facing occupied France.

Managed partly by the National Trust, the clifftops are perfect for brisk walks across grassy fields overlooking busy shipping lanes, where you can often spot ferries and the French coast on a clear day. A trail leads to the Victorian South Foreland Lighthouse, while hidden below are the tunnels of the Fan Bay Deep Shelter, a former wartime battery open for guided tours. Local wildflowers, butterflies, and seabirds only add to the beauty of this striking coastline.