8 Best Sights in Rye, The Southeast

Immortalized in paintings, photographs, and films, Bodiam Castle (pronounced Boe-dee-um) rises out of the distance like a living piece of medieval legend. From the outside, it's one of Britain's most impressive castles, with turrets, battlements, a glassy moat (one of the very few still in use), and 2-foot-thick walls. However, once you cross the drawbridge to the interior there's little to see but ruins, albeit on an impressive scale. Built in 1385 to withstand a threatened French invasion, it was partly demolished during the English Civil War of 1642–46 and has been uninhabited ever since. Still, you can climb the intact towers to take in sweeping views of the surrounding vineyards and countryside, and kids will love running around the keep. The castle, 9 miles northwest of Rye, schedules family-focused activities during school holidays. For a unique way to approach Bodiam Castle, take a 45-minute river cruise through the pretty Sussex countryside. Boats leave from the riverbank in Newenden; find more information and sailing times at  www.bodiamboatingstation.co.uk.

This small town, a few miles southwest of Rye, perches prettily atop its own small hill amid rolling farmland, and has a number of interesting attractions. There's the splendid (though damaged) church at its heart, built in the 14th century with stone from Normandy. The stained glass windows are particularly captivating, with renowned Scottish artist Douglas Strachan (1875–1950) creating an almost three-dimensional effect with his bold illustrations. Outside the church lies a grave with a much-quoted epitaph. English-Irish comedian Spike Milligan (of The Goon Show fame), who was buried here in 2002, requested that the words "I told you I was ill" be added to his gravestone. The diocese refused, but compromised by writing it in Irish instead. Walk around the graveyard and see if you can spot the headstone with the words: "Dúirt mé leat go raibh mé breoite."

Under the town's narrow streets are at least 56 medieval cellars, with some accessible by an interesting—if rather long—guided tour (£12) on various dates from April to October. A short walk from the town center is Winchelsea Beach, an attractive stretch of shingle coastline.

After decades—centuries, even—as the butt of jokes, the English wine industry is now being taken more seriously, with English wines winning some prestigious international awards. Drop in at Chapel Down Winery, one of Britain's leading wine producers, to see for yourself. You can visit the wine shop and explore the herb gardens for free, or pay for a two-hour-long guided tour of the rest of the grounds with tasting—advanced booking is advisable in summer. Other themed tour experiences are available, too. The winery is 6½ miles north of Rye.

At the top of the hill at the center of Rye, this classic English village church is more than 900 years old and encompasses a number of architectural styles. The turret clock dates to 1561 and still keeps excellent time; its huge pendulum swings inside the church nave. Climb the tower for amazing views of the surrounding area.

Combining a large timber-frame hall with an inventive cottage garden on a grand scale, this place will get your green thumbs twitching. The house dates to 1464 (you can tour a few rooms) and was restored in 1910 by noted architect Edwin Lutyens, who also designed the garden. From these beginnings, the horticulturist and writer Christopher Lloyd (1921–2006), whose home this was, developed a series of creative, colorful "garden rooms" and a dazzling herbaceous Long Border; Fergus Garrett continues to develop this stunning garden. The house is 7 miles northwest of Rye.

There's something about Lamb House, an early-18th-century dwelling in the heart of Rye, that attracts writers. The novelist Henry James lived here from 1898 to 1916, while E. F. Benson, onetime mayor of Rye and author of the witty Mapp and Lucia novels (written in the 1920s and 1930s), was a later resident. The ground-floor rooms contain some of James's furniture and personal belongings.

This is one of the town's original cobbled streets, and perhaps its most quintessential view, which heads steeply from the top of the hill to the former harbor. Its name supposedly came from the night a drunken sailor swore he heard a mermaid call him down to the sea (back when Rye was still a seaside town). The houses here date from between the medieval and Georgian periods; a much-photographed pair have the delightfully fanciful names "The House with Two Front Doors" and "The House Opposite." Be careful on your feet—the cobbles are very uneven.

Down the hill past Church Square, Ypres Tower—pronounced "Wipers" by locals—was originally built as part of the town's fortifications (now all but disappeared) in 1249; it later served as a prison. A row of defensive cannons is fixed to the rampart overlooking the (disappointingly industrial) edge of Rye and several miles of flatland beyond. When they were installed, however, the canons pointed directly out to sea. Inside the tower is the Rye Castle Museum (RCM), which has displays on the city's history, from medieval floor tiles to 15th-century suits of armor, as well as an interesting exhibition on 1830s life as a female prisoner in the "women's tower."

A second (free to enter) outpost of the RCM at nearby 3 East Street has more exhibits, including examples of Rye pottery, for which the town was famous, and a fire engine that was built in 1745 and served the town for 120 years.