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This improbably perfect small medieval town was one of the Cinque Ports that supplied ships to the Navy in return for privileges from the king. Placed on a hill crowned by the partly Norman church, its partly cobbled streets are on an early medieval layout, and many houses date from the 16th and 17th centuries. Mermaid Street, with the timber-framed Old Mermaid Inn (a smugglers haunt in the 18th century), is particularly photogenic, while Landgate marks what was the only landward entrance when the sea came right up to the town (it's now a couple of miles out). The High Street has a remarkable array of buildings, including the Old Grammar School with its Dutch gables.
There are antique shops, book shops and craft shops for browsing and the heritage centre on Strand Quay is useful introduction to the town's history - from here you can rent a self-guided audio tour. For more local history it's worth seeking out the displays in the Rye Castle Museum and in the 13th-century Ypres Tower. Lamb House in West Street dates from 1723 and is owned by the NT (open a couple of afternoons a week); it commemorates two authors who lived here, Henry James and (later) E F Benson whose Mapp and Lucia stories are set in Rye.
The hamlet of Rye harbour is down by the coast; here the Inkerman Arms has good fresh fish, and the shingle expanse around the river estuary is a nature reserve with hides for watching shore birds. For bathing, the best sandy beach in the area (and arguably the finest in the South-East) is a bit further east at Camber Sands, with miles of safe, clean sands.
Drive west on the A259 to Winchelsea. On the way you will see the massive Tudor fort of Camber Castle on the left, which like Rye and Winchelsea was originally by the sea.