Is this the ultimate city break? Winchester has it all: from ancient history to space exploration, plus cafes, cocktails, culture and countryside… But with so much to do, choices are going to have to be made

Morning

Decisions, decisions. Winchester is a TARDIS. Where are you going to go - past or future?

For history nerds a visit to Winchester Cathedral is obvious. Guided tours include the soaring 15th century stone screen, 12th century wall paintings, richly coloured stained-glass windows by pre-Raphaelite artist Edward Burne-Jones and the largest surviving spread of Medieval decorated floors inside any building in England. There are tours down to the crypt, with its contemplative sculpture by Antony Gormley, and up the tower for dizzying views over the rooftops.

Cross the Cathedral’s inner close, past Cheyney Court with its instagrammable jettied timbered gables, under Priory Gate and Kingsgate – one of two remaining Medieval city gates. This one has a small church over it, St Swithun-upon-Kingsgate, aka St Cuthbert’s in Anthony Trollope’s novel The Warden. Turning left into College Street there is another literary connection - the house where Hampshire’s best-known author, Jane Austen, died. Further along is the entrance to Winchester College where occasional tours explore the College’s medieval heart including its 14th century Gothic Chapel which makes an appearance in the film of Les Misérables.

Other places worthy of pondering times past include: the 12th century ruins of Wolvesey Castle, once one of the greatest Medieval buildings in England; City Museum which includes a unique record of Winchester – a scale model of the city in 1870; and Westgate Museum, the second surviving Medieval gateway, this one with fine painted ceiling made for the visit by Mary Tudor and Philip of Spain on their marriage in Winchester Cathedral in 1554. There’s also the Great Hall; this fine 13th century aisled hall is all that remains of Winchester Castle and is home to what is said to be the Round Table of Arthurian legend. At the other end of the city centre, the National Trust is undertaking a major conversation project at Winchester City Mill, the country’s oldest working watermill. Work is due to be completed late September with new visitor facilities installed over winter including a café with produce made from the Mill’s own ground flour. Meanwhile milling demonstrations continue Wednesday, Saturday and Sunday.

Budding space engineers will prefer exploring the shiny space age dome and pyramid of Winchester Science Centre & Planetarium on the city’s outskirts. This leading science and discovery centre has the largest standalone planetarium cinema in the UK and a new attraction Explorer:Space, officially launched in July by NASA Astronaut Michael Foale. It’s an immersive space experience designed to wow families by taking them on an epic adventure through the universe with exhibits encompassing coding to robots, atmospheric pressure to space flight. Meanwhile the 360° fulldome planetarium offers an exciting programme with films, such as Faster than Light, a new film narrated by Sean Bean, and presenter-led shows where the planetarium is used as a flight stimulator.

Coffee Break and Lunch

Café culture in Winchester is thriving with plenty of great places to relax over coffee and cake. Among them are: Café Monde and Coffee Lab, both in The Square with outside seating (the original Coffee Labs can still be found nearby on Great Minster Street and St Thomas Street); Rawberry for healthy juices and veggie bites; Chococo for totally indulgent Chocolate Afternoon Tea; Corner House with eclectic drawing room style; and Bridge Street Patisserie, Winchester’s oldest coffee shop. I’m also hearing good things about Copper Joes among the military museums in Peninsula Square.

Afternoon

Shopping or scenery? Countryside is so close to the city centre you may manage both. St Giles Hill provides the opportunity to work off lunch and enjoy views across King Alfred’s statue and Cathedral. There are also riverside walks along the River Itchen and through the water meadows - thought to have inspired Keats to write his ode To Autumn.

However, shoppers are in for a treat. Tucked among impressive names on the High Street (spot Space NK and The White Company) is the occasional independent such as Jeremy France Jewellers with on-site workshop for bespoke commissions as well as covetable pieces like Fope’s contemporary mesh chains. Otherwise Idiosyncratic indies are found on the side streets. Eclectic Hound on The Square and The Mantique on Parchment Street are both sartorial troves for original menswear. Explore Jewry Street for John Lewis of Hungerford, the original painted kitchen company, handcrafting bedroom and kitchen furniture including traditional stools in shades of pink and yellow. You’ll also find Consortium with cool vintage furniture and wearable fashion from Mint Tea Boutique (on the first floor). Meanwhile Southgate Street has become really interesting with the recent arrival of Sass & Edge fashion boutique, Cartridge Fine Art - a glam mash up of the flamboyant, the striking and the iconic, check out images from Terry O’Neill’s archives recreated as diamond dust silkscreens (one client is Claudia Schiffer), and Blubambu selling in vogue eco homestyle including chairs from recycled oil drums, handblown glass from Bali and reclaimed teak reinvented as unique crafted furniture.

Evening

Choose from a cinema converted from an old army chapel with armchairs, plenty of leg room and bar, or Theatre Royal, the only surviving cine-variety theatre in the country.

But eating and drinking is probably Winchester’s big draw. This foodie hot spot has attracted top names. Brasserie Blanc is celebrating its tenth anniversary in the city, Rick Stein opened his first restaurant outside Cornwall here, around the same time Hugh Fearnley Whittingstall opened River Cottage Canteen in restored Abbey Mill. They have recently been joined by The Ivy.

But Winchester’s independent eateries are superb. There’s Michelin-starred and distinctively different Black Rat, Good Food Guide-recommended Chesil Rectory, also celebrating ten years this summer and combining refined comfort food with vintage chandeliers in this 15th century Medieval building. Plus, there’s Kyoto Kitchen for contemporary Japanese and Three Joes for tasty sourdough pizzas - just opened on Great Minster Street. For pre or post-dinner drinks, try seductively dark Cabinet Rooms (opposite the Theatre) serving seriously good cocktails, The Green Man (opposite the Cinema) for great wines by the glass (good nosh, too), and Incognito, a drinking den channelling Phileas Fogg in the basement of St John’s House.

Sleeping

Take your pick from two cool and comfy B&Bs: Hannah’s, stylish home from home hidden off Parchment Street, and characterful and quirky The Black Hole on Wharf Hill. Two charming pubs with rooms include The Old Vine, an 18th century inn overlooking the Cathedral with luxurious suites and The Wykeham Arms, voted Town Pub of the Year 2018 by The Good Pub Guide. Not forgetting the original Hotel de Vin, a boutique hotel in an elegant 18th century townhouse with bistro, courtyard garden and cossetting rooms.

My Winchester - Gary Whiter, Cabinet Rooms

“Marcus Roe and I founded Cabinet Rooms back in 2014 as a blog about food and drink. We love living in Winchester and have great fun exploring the area and its produce, and the main purpose of Cabinet Rooms was to share that experience. It wasn’t long before we started running small events. These have grown over the years into a programme of cultural events (our Secret Underground Film Society has over 300 members!) and we are now responsible for five festivals in the area.

“Winchester Cocktail Week starts the city’s annual festival programme every February and there’s an abundance of events and activities throughout the year leading up to the Cathedral’s Christmas Market. We shall also be running our own — albeit alternative — Ginchester Christmas Market at the Great Hall on Saturday 1 December 2018; a fantastic opportunity to sample and buy local, craft spirits in time for the party season.

“The city also has a fantastic coffee scene, driven by coffee heroes who love what they do and serve up exceptional cups of coffee! Look past the coffee chains around the High Street, there’s a host of independent coffee shops.”

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