Southeast from London, through Kent and Sussex to England’s southern coast, the land is fertile and the climate mild. Scores of narrow country lanes twist and turn among the gentle slopes of the pleasant countryside, leading you from Chartwell, Churchill’s home, through castles, manors, and some of the most exquisitely beautiful gardens in England to Rye, a town full of history and rich in smugglers’ tales. Along the busy, crowded coast you come to Brighton, where seaside honky-tonk contrasts with the vivid spectacle of the onion domes of the Royal Pavilion, Arundel with its mighty fortress, and Portsmouth with its historic boats.

Recommended Pacing: Spend two nights in southeast England to enable you to accomplish the first part of this itinerary. Allow a day’s drive, with sightseeing, along the coast and into Winchester. Spend two nights in Winchester to give you a complete day for sightseeing.

Chartwell, your first sightseeing destination, lies 9 miles from exit 6 of the M25, through Westerham and onto country lanes. Chartwell was the home of Winston Churchill from 1924 until his death in 1965, when Lady Churchill gave the house and its contents to the nation. To visit this large home and Churchill’s studio, full of his mementos and paintings, is to have a glimpse into the family life of one of Britain’s most famous politicians.

Leave Chartwell to the left following the country road a short distance to Hever Castle, a small 13th-century moated castle that was at one time home to the Boleyn family. Anne Boleyn was Henry VIII’s second wife and Elizabeth I’s mother. At the turn of the last century vast amounts of money were poured into the castle’s restoration by William Waldorf Astor, an extremely wealthy American who forsook his native country and became a naturalized British citizen. Because the castle was far too small to provide accommodation for his family and friends, Mr Astor built an adjacent village of snug, Tudor-style cottages and joined it to the castle. While the village is not open to the public, the restored castle, its rooms full of antiques that span the last 800 years, and the parklike grounds are open to visitors.

Leave the castle heading left in the direction of Tunbridge Wells, turning left down a small country road to Chiddingstone, a National Trust village, whose short main street has several 16th- and 17th-century, half-timbered houses, a church, and a teashop. Park by the old houses and follow a footpath behind the cottages to the Chiding Stone, from which the village gets its name: nagging wives were brought here to be chided by the villagers.

Just beyond the village, branch left at the oast house for Penshurst Station and Penshurst Place, a 14th-century manor house with an Elizabethan front surrounded by magnificent parkland and gorgeous gardens. Here Sir Philip Sidney-poet, soldier, and statesman-was born and his descendant, Viscount de l’Isle, lives today. The enormous, 14th-century great hall with its stone floor and lofty, ornate, beamed ceiling contrasts by its austerity with the sumptuously furnished state rooms. There is also a fascinating collection of old toys. The gardens are a delight, full of hedges and walls that divide them into flower-filled alleyways and rooms-each garden with a very different character.

Tunbridge Wells lies about 7 miles to the south. In its heyday Royal Tunbridge Wells rivaled Bath as a spa town. The Regency meeting place, The Pantiles, a terraced walk with shops behind a colonnade, is still there as are the elegant Regency parades and houses designed by Decimus Burton. Central parking is well signposted to the rear of the Corn Exchange, which contains an exhibit, Day at the Wells, which traces the town’s growth from the time the spring water became fashionable for its curative powers to its popularity with wealthy Victorians.

Leave Tunbridge Wells on the A267 following signposts for Eastbourne till you are directed to the left through Bells Yew Green to cross the A21 (Hastings road) and enter Scotney Castle Gardens (NT), a gorgeous, romantic garden surrounding the moated ruins of a 14th-century castle.

Leave Scotney Castle Gardens to the left, taking the A21 (Hastings road) for a short distance to Flimwell where you turn left on the A268 to Hawkshurst and from here left on the A229 Maidstone road to Cranbrook. While it is not necessary to go through Cranbrook to get to Sissinghurst Gardens, it makes a very worthwhile detour because it is a delightful town whose High Street has many lovely, white-board houses and shops, a fine medieval church, and a huge, white-board windmill with enormous sails. On the other side of town you come to the A262 where you turn right for the short drive to Sissinghurst Castle Gardens.

Sissinghurst Castle (NT) was a jail for 3,000 French prisoners in the Seven Years’ War. Its ruined remains were bought by Vita Sackville-West and her husband, Harold Nicolson, in 1930 and together they created the most gorgeous gardens with areas divided off like rooms, each with a distinctly different, beautiful garden. They also rescued part of the derelict castle where you can climb the tower in which Vita wrote her books. At the entrance to the garden an old barn has been tastefully converted into a tearoom and shop.

Continue along the A262 to Biddenden and take the A28 through Tenterden with its broad High Street of tiled and weather-boarded houses to the A268 (Hawkshurst road) where you turn right for the short drive to the village of Sandhurst. Here you turn left onto country lanes to Bodiam Castle (NT), a small, picturesque, squat fortress with crenelated turrets surrounded by a wide moat and pastoral countryside. Richard II ordered the castle built as a defensive position to secure the upper reaches of the Rother against French raiders who had ravaged nearby towns, but an attack never came.

Turn left as you leave the castle, following a country lane to Staple Cross where you turn left on the B2165, which brings you into Rye, a fortified seaport that was often attacked by French raiders. However, the sea has long since retreated, leaving the town marooned 2 miles inland. Find the quaintest street in Rye, Mermaid Street, with its weatherboard and tile-hung houses and up one cobblestoned block you find yourself on the doorstep of The Mermaid Inn. Opened in 1420, The Mermaid Inn is a fascinating relic of the past. As late as Georgian days, smugglers frequented this strikingly timbered inn and used to sit drinking in the pub with their pistols on the table, unchallenged by the law. Near the Norman Church is the 13th-century Ypres Tower-formerly a castle and prison, it is now a museum of local history. Lamb House (NT) (on West Street near the church) was the home of American novelist Henry James from 1898 to 1916. To learn more about Rye’s fascinating history attend the sound and light show at the Rye Town Model.

Leave Rye on the A259, taking this fast road around Hastings and Bexhill to Eastbourne where you follow signs for the seafront of this old-fashioned holiday resort and continue on to the B2103, which brings you up and onto the vast chalk promontory, Beachy Head, rising above the town. It is a glorious, windswept place of soaring seagulls and springy turf, which ends abruptly as the earth drops away to giant chalk cliffs plummeting into the foaming sea. This is the starting point for the South Down’s Way, a popular walking path. Passing the Belle Tout Lighthouse, you come to Birling Gap, a beach once popular with smugglers but now favored by bathers. The most dramatic scenery, the Seven Sisters, giant, white, windswept cliffs, are an invigorating walk from the visitors’ center.

Your next destination is Alfriston, an adorable village on the South Downs Way which traces its origins back to Saxon times. Behind the main village street in a little cottage garden facing the village green sits the Clergy House (NT) with its deep thatched roof, the first building acquired by the National Trust, in 1896.

Either the fast A27 or the slower coastal road (A259) will bring you into Brighton, a onetime sleepy fishing town transformed into a fashionable resort at the beginning of the 19th century when the Prince Regent built the fanciful, extravagant Royal Pavilion with its onion domes and gaudy paintwork. Follow signs for the town center and park near the pavilion, an extravaganza of colorful, rather overpowering decor. Very near the Royal Pavilion are The Lanes, narrow streets of former fishermen’s cottages now filled with restaurants and antique and gift shops. The seafront is lined by an almost 3-mile-long promenade with the beach below and gardens and tall terraces above. Many of the once-fashionable townhouses are now boarding houses and small hotels but this does not detract from the old-fashioned seaside atmosphere of the town. Stretching out into the sea, the white, wooden Palace Pier harks back to an earlier age. At the end is a delightful, old-fashioned funfair with a helter-skelter and carousel horses along with other rides.

Leave Brighton along the seafront in the direction of Hove to join the A27 at Shoreham-by-Sea. This section of the A27 passes through suburb after suburb and is the least interesting part of this itinerary. On the outskirts of Arundel the massive keep and towers of Arundel Castle rise above the town. Built just after the Norman Conquest to protect this area from sea pirates and raiders, the castle contains a collection of armor, tapestries, and other interesting artifacts.

From Arundel take the A284 inland towards Pulborough and then follow signs through the narrow, winding old streets of Petworth, proffering several antique stores, to Petworth House (NT), an enormous, 17th-century house in a vast deer park with landscaping by Capability Brown. The house, completed by the 6th Duke of Somerset in 1696, retains the 13th-century chapel of an earlier mansion and houses a proud art collection, which includes a series of landscapes by Turner and also paintings by Holbein, Rembrandt, Van Dyck, Gainsborough, Titian, Rubens, and Reynolds.

Retrace your route the short distance into Petworth and take the A272 through Midhurst to reach the A286 (Chichester road). Midhurst has some fine old houses and attractive inns. Knockhundred Row leads from North Street to Red Lion Street and the old timbered market. Curfew is faithfully rung each evening at 8 pm in the parish church. Legend has it that a rider, lost in darkness, followed the sound of the church bells and found his way to the town. To show his gratitude he purchased a piece of land in Midhurst, now called Curfew Garden, which he presented to the town as a gift and made money available for the nightly ringing of the bells.

Across the South Downs the A286 brings you to the Weald and Downland Museum, an assortment of old, humble buildings such as farmhouses and barns brought to and restored on this site after their loss to demolition was inevitable. Inside several of the structures are displays showing the development of buildings through the ages.

Leaving the museum, take the A286 around Chichester to the A27 Portsmouth road, which leads you onto the M275 to the historic center of Portsmouth and your goal, the H.M.S. Victory and Mary Rose. The H.M.S. Victory, Nelson’s flagship at the Battle of Trafalgar in 1805, has been restored to show what life was like on board. Nearby, the Mary Rose, Henry VIII’s flagship, is housed in a humidified building that preserves its remains, which were raised from the seabed several years ago. The Naval Museum has a display of model ships, figureheads, and a panorama depicting the Battle of Trafalgar.

Retrace your steps up the M275 and onto the M27, which quickly brings you to the A33/M3 and Winchester where a magnificent Winchester Cathedral stands at the center of the city. Park in one of the car parks on the edge of town and walk into the pedestrian heart of the city, which was the capital of England in King Alfred’s reign during the 9th century and stayed so for 200 years. Construction of the 556-foot-long cathedral began in 1079 and finished in 1404. Treasures include a memorial window to Izaak Walton, a black marble font, seven chancery chapels for special masses, medieval wall paintings, stained glass, and tombs of ancient kings including King Canute. Close by is Winchester College, founded in 1382, one of the oldest public (i.e., private) schools in England. At the top of the High Street is a fascinating area that has formed an important part of the city’s defenses since Roman times. Here you find the 13th-century Great Hall, the only surviving part of Winchester Castle and home to the legendary Round Table which has hung on the wall here for 600 years. Military history buffs will enjoy the five Winchester Military Museums, which offer guided tours by arrangement.

Leaving Winchester, the M3 will quickly take you back to London.

* (NT) means that the property listed is under the care of the National Trust.

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