Grab a holdall for 48 hours in Rother that includes wine, jazz, ghosts, castles, Art Deco art galleries and coastal walks.

The Rother District of East Sussex has 37 km of coast, a dozen historic towns and villages such as Rye, Winchelsea, Bexhill and Battle, ancient castles, art galleries and vineyards. It stretches from Camber Sands in the east, up to Wadhurst near Tunbridge Wells and down to Pevensey Bay (but it does not include Hastings).

Friday afternoon arrival
Start your 48 hours in Rye and spend late Friday afternoon exploring this small but hopelessly picturesque Medieval town with its cobbled streets and heady views. Arrive before 4 pm and you can climb up the church tower (St Mary’s Church right in the centre at Church Square) to get panoramic views of the town and visit the town’s ancient city gate. And make sure you take a stroll down Mermaid Street before sunset – it’s one of the most photographed streets in Britain.

Friday evening
There are lots places to eat in Rye but if it’s atmosphere and history you’re after then try The George (which is a 16th century coaching inn in the High Street), The Mermaid Inn (which dates back to the 11th and 14th century and comes with ghosts, hidden passageways and tales of smugglers) or The Old Bell, which has an 80 year old wisteria and was built in 1390 (you’ll find it in the Mint at the other end of the High Street to The George).

Once filled with a sense of Rye’s charm, history and dinner, make your way along to The Grapevine in Conduit Hill (off the High Street), Rye’s Champagne and Jazz bar and the place to go for an evening of jazz and cocktails! Or, if you’re an ale aficionado, head to the Rye Waterworks Micropub which you’ll find in an old water pump house.

Saturday morning
Having got your bearings last night, it’s time to explore this ancient Cinque Port and the surrounding area in a little more depth. Lamb House is not far from the church and is a National Trust property and the Ypres Tower is a museum. Both are worth a visit before you head out of town to Rye Harbour.

There is a discovery centre here but you might just want to enjoy a cobweb blasting walk from the Martello Tower past the famous black and red fishermen’s hut along to the sea front to build up an appetite for lunch. And for this, try the Globe in the Marsh. It’s eclectic and you can try local produce like Rye Bay scallops or Hastings 1066 Gin.

Saturday afternoon
After lunch, head inland toward Battle, and the site of the famous Battle of Hasting in 1066 when William the Conqueror defeated King Harold as part of the Norman invasion. The main place to visit here is Battle Abbey and the battlefield. This will take a couple of hours and then there is just time to explore some of the shops up the High Street. There is a tap room, an antique emporium and antique jewellery shop as well as a deli and wine shop selling lots of local produce.

Saturday night
For Saturday night, check availability at Oastbook Vineyard near Robertsbridge. They host a Summer Party in June and fine wine and dining evenings. You can also stay there if you don’t want to drive.

Sunday morning
For the last part of your 48 hours in Rother, you have a decision to make. You can head to the coast for some culture at the Art Deco style De La Warr Pavilion in Bexhill, where they have an ongoing programme of exhibitions, concerts and events. If you do, make time for a walk along the Colonnade and then have lunch at the Sackville Bistro. If you go inside the building here, there’s lots of information about Bexhill’s motor racing past!

Alternatively, from Battle head to Bodiam Castle, a 14th century, moated National Trust castle that stands in ruins but is well worth exploring. In summer, you can also take a boat ride back to Rye from Bodiam Boating Station. Or simply head to one of the local vineyards like Carr Taylor or Oxney Organic Estate for a vineyard tour and tasting, and of course, to stock up with some vintage souvenirs to take home.

Places to stay in Rye
There are quite a few fabulously quirky places you might want to stay in Rye. There is Rye Windmill on the outskirts of the town, or of course, the famous Mermaid Inn. Alternatively, try Jeake’s House – a 17th century hotel also in Mermaid Street. 10 miles from Rye, you’ll find Railway Retreats at Northiam where you can stay in a customised train carriage.

Places to stay in Battle
You could stay right on the edge of the battlefield and within walking distance of the Abbey at South Lodge – a two-bedroom holiday cottage. Or try Powdermills Country House Hotel. It’s about a mile from Battle centre and has acres of gardens, park and woodland.

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