Rye might have a tumultuous past of Gallic invasions, smuggling and blitz devastation, but its present has settled into a more sedate clinking of teacups, antique seeking and shopping for tasteful throws — the only disturbance being the ‘oyez, oyez, oyez’ bellowed by a town crier.
But don’t be lulled into thinking Rye and its surrounds are ‘sleepy’: nearby, vintners grow funky, biodynamic Pet Nats, Michelin stars are a’shooting, the long-established arts scene has a new guard, and an on-the-horizon members’ club is making South Saxons seem all-the-more cosmopolitan. So, come spend a charming 48 hours in Rye and beyond.
FRIDAY EVENING

The George Inn Rye
With its fortifications, cobbles and wonky mediaeval buildings, Rye has clung onto its historic prettiness as tenaciously as it has English rule (even if it was, at one point in the 13th century, part of France). As the totem of 1066 Country, set above the arcadian dais of Rye Harbour nature reserve and crowned with Ypres Castle, it’s an excellent first-impression-maker for East Sussex.
Even its train-station is Grade-II-listed. From there, lug your case up Market Road to the High Street, where past-and-present-straddling stay The George puts you at the centre of the citadel; a fine base before you explore Rye’s leafier outskirts, staying at wine estate Tillingham and coastal retreat The Gallivant. The hotel dates to 1719, and — while it’s been upgraded in the ensuing centuries — it still has Elizabethan beams, an original parliamentary clock and store where 18th-century guests would stash their wigs. Current owners Katie and Alex Clarke worked respectively in an art department for film and TV and as a hotel consultant — the ideal duo for modernising the hotel.
Book for the evening at The George Grill and you’ll get East Sussex on a plate: Rye Bay scallops and fish; Romney Marsh lamb; chicken with smoked tomato and cockles (a Brit surf ‘n’ turf); and chocolate mousse in tarragon cream. For a nightcap, the hotel’s Dragon Bar has local ales and inventive cocktails. Or edge halfway down steep, cobbled Conduit Hill for jazz and English sparklings at The Grapevine till 1am.
SATURDAY MORNING
If your head rings with fizziness and trumpet solos on waking, The George will sort you out with a breakfast toastie or full-English, washed down with mimosas. Georgian-era brunching spot the Whitehouse, a few doors down, has hashes galore (salmon, halloumi, mackerel…), served in elegant, panelled halls, and wellness shots to juice you up for the day.
Then, shake off the cobwebs — of Rye’s past, that is. Hike up Lion Street to St Mary’s Church, which is around 1,000 years old and home to the oldest working church-turret clock in the UK. Seek out Pre-Raphaelite artist Sir Edward Burne-Jones’ stained-glass window, then stroll through the graveyard, site of a still-discussed 18th-century murder.
Nearby, Ypres Castle’s 13th-century look-out has been a fort with a gun garden, prison and morgue, and now hosts a small museum. From the battlements, there’s a clear view of the salt marshes, harbour and North Downs. If you find tales of naval battles and prison rations a tad dry, whet your whistle next door at The Ypres Castle Inn next door, whose garden is the place to be in the summer.
After, go through the castle’s Gun Garden, swing back to West Street and to Lamb House, Rye’s literary locus. Writer Henry James moved here, seeking a ‘lowly refuge’ and finding an estimable one, and entertained an elite circle, from Virginia Woolf to H.G. Wells. Dressed in James-era finery, it’s a snapshot of fin de siècle life, and art exhibitions are hosted in its one-acre garden.
SATURDAY AFTERNOON

Mermaid Inn
Mermaid Street is Rye’s supermodel — it’s de rigueur to get a snap from the top. A wattle-and-daubed catwalk, one of the UK’s best-preserved mediaeval streets, it has some curios, including ‘The House Opposite’; named so smugglers would know to go to the 15th-century Mermaid Inn across the street.
This was the hangout of the Hawkhurst smuggling gang, who’d menacingly display their pistols on the bar tables. The hostelry’s past is writ in secret entrances; priest holes tucked into chimneys and heraldry-painted panels. Stop for a Mermaid Martini and other spirits may appear: grey ladies, mysterious orbs and ‘cold spots’ have been reported. But take 18th-century ghost stories with a pinch of tariffed salt — many were ruses to divert people from smuggler shenanigans.
For lunch, turn into picturesque road The Mint for bougie burgers at Hoof, or dine among farmers, writers and history buffs at The Standard Inn. Then brace yourself for the many tasteful objets you’ll want to buy: forgotten vinyl at The Other Record Shop; hand-forged candleholders and seagrass baskets at Rae; pinecone vases and sea-salt candles at Mundus; and recycled Elliker backpacks from Sailors. Find sustainable fashion in Through Your Wardrobe, which stocks pre-loved, known and niche labels; and Les Animaux, with its considered clothing edit, love of local artisans and mending workshops.
SATURDAY EVENING
From The George, stroll down East Cliff to the Landgate, a 14th-century defence against invaders. Along Tower Road, several eateries battle for your attention. Webbe’s at The Fish Café serves crab arancini and upmarket fish and chips (with a cookery school upstairs if you really want to dive in). No. 50 is more experimental, with dishes such as hake Kyiv with nduja, and lamb with black-garlic ketchup. Top off your night at the CAMRA-approved Waterworks Micropub and brewery, or head to The Old Bell, Rye’s most antique drinkery, dating back to the 14th century.
SUNDAY MORNING

Rye House Antiques
Rise, shine and rush to The Fig, the social darling of Rye, with coveted tables (book in advance) and laden waffles balanced out with veggie-forward options. Don’t linger, because there’s still time to squeeze in another homewares hunt. Designer-run Soap & Salvation (in the former Salvation Army chapel) has an impeccable curation of vintage wants. Rye House Antiques specialises in mid-century finds, and Puckhaber has weathered French fancies.
SUNDAY AFTERNOON
If it’s sunny, head to the alfresco seafood stand outside Rye’s Fishmarket. The industry may have waned with the tide, but the sea’s offering is still strong. Or head further afield: a 10-minute drive south of Rye is The Gallivant, a cosy roadside stop-off with a coastal look and a communal garden. Eatery Harry’s shows the upturn in French-British relations since the 11th-century — its ex-Bibendum chef serves up superbe tartares and terrines alongside a beefy Sunday roast. It’s across the road from Camber Sand dunes: soft, shifting scenery dotted with tufts of seagrass.
Drive east, past marshland, to the shingle spits of Dungeness. With its nuclear power station in the distance, it has a post-apocalyptic feel; but Prospect Cottage, where radical filmmaker Derek Jarman retreated after his AIDS diagnosis, is a sanctuary amid the desolation, where artists often take up residency, still with the glorious garden he nurtured.
Battle, a 30-minute drive from Rye, is home to the field where the Battle of Hastings was fought. After you’ve gazed on it, find a cosy corner at the Abbey Hotel for pints of local ale and a glass of Sussex fizz, and maybe an extremely generous ploughman’s platter to pick at.
SUNDAY EVENING

Tillingham
Tillingham (a 15-minute drive from Rye) is a wine estate with a bold approach to production of natural and biodynamic bottles. Its restaurant gives its Earth-kind best too — earning a Green Michelin Star in the process — with local-ingredient dishes such as goat’s cheese mousse with grilled peaches, or gnocchi in nasturtium pesto. Should you wish to tip 48 hours into 72 — or if you’ve over-imbibed the Pet Nat — there are stylish rooms to crash in.
NEED TO KNOW
Transport London Gatwick is the closest airport to Rye, a 90-minute drive away; trains from London St Pancras arrive at Rye via Ashford in just over an hour, making it an easy weekend-break getaway from London.
When to go Summer in Rye feels like the old days of invasion, as tourists spill in. Arrive in spring and it’ll be quieter, and you may spy newborn lambs in the surrounding marshes. The citadel is magic come the festive season, with open fires to huddle by, a lively festival and lights that make it look like a Christmas card.
What to buy Rye pottery is a craft carried on for centuries, straddling the line between style and whimsy, with colourful vases or figures from the Bayeux Tapestry. You can see them being made in the upstairs workshop at The Old Brewery, too.
Good to know Tillingham is but a drop in a barrelful of East Sussex vineyards — nominate a designated driver and take tasting tours at Chapel Down, Oastbrook, Oxney, Gusbourne, and more bijou sites like Sedlescombe.
Check out more of the county with our full collection of hotels in Rye and East Sussex



