Ranked among the most picturesque streets in Britain, Mermaid Street is the kind of charming ramshackle scene you’d expect to see on a shortbread tin. After a scroll-stopping snap for your Instagram feed? This is your place. Draped in leaves, half-timbered Tudor buildings with names such as “The House with Two Front Doors” and “The House Opposite” tumble down a cobbled hill. Best visited in May when the wisteria is in full bloom.

Rye’s fascinating past is told through its historic architecture – along the streets you’ll spot a 15th-century prison door as well as 18th-century vaulted cellars, a relic from Rye’s heyday as the smuggling capital of England. The town’s medieval incarnation as Cinque Port, when it served to defend England against invasion from continental Europe, is best understood through a visit to Ypres Tower and Rye Castle Museum. We also recommend visiting the 12th-century St Mary’s Parish Church – the views from the tower are the main draw here. Gaze over the Rye’s rust-tiled rooftops to the rolling Sussex countryside and, on a clear day, the windswept shores of Winchelsea in the distance.

Rye’s captivating heritage isn’t all rooted in medieval times. Literary heavyweights Henry James, E. F. Benson and Rumer Godden have all lived in this handsome Georgian house. Now owned and run by the National Trust, it opens to visitors in summer. Once you’ve ogled its collections, head to its walled garden for a tea-and-cake pit-stop to gear up for heading back to the hubbub of central Rye. Artistically inclined? While you’re about town, make the literary pilgrimage (read: 25-minute drive) to the wild expanse of Dungeness, where Derek Jarman’s Prospect Cottage is backed by shingle shores strewn with skeletons of old ships.

Some 450 acres of salt marsh, beach and woodland make this nature reserve one of the UK’s most important wildlife conservation sites – don’t be surprised to find a few twitchers hanging about here. A web of paths take visitors through a patchwork of grazing marshes, freshwater gravel pits and reed beds. While you’re here, we’ll let you in on a local secret: Bosun’s Bite. This no-frills café in Rye Harbour serves a great fry up – best enjoyed with a steaming cuppa before a walk to the nearby dunes of Camber Sands.

Typically held over the August bank holiday, this five-day festival is among Rye’s headline summertime attractions, drawing big-name jazz and blues artists – Beverley Knight, Richard Thompson, Rumer – to perform in and around the ethereal St Mary’s Parish Church. Elsewhere on the Rye events calendar, you’ll find Rye Bay Scallop Week in February, the Rye Society of Artists Summer Exhibition in August and the popular Rye Arts Festival in September. Bonfire night and Christmas Festivals are particularly good too.

A scenic 15-minute drive north of Rye, this lush, award-winning wine estate (the official supplier to No.10 Downing Street) makes you realise why Kent is called the “Garden of England”. Tour the vineyards before lunch in its restaurant, The Swan. Stomach lined, treat yourself to a tasting session of its bounty of bevvies, including sparkling wines, gin, vodka and cider. Stocking up on a few bottles to take home is recommended.