Jerez de la Frontera is a classically Andalusian city with lashings of old-school Spanish charm. Crumbling medieval walls hide tapas restaurants and classic tabancos (little working-class bars), which peddle crisp sherry from £1 a glass. Wander the streets and you will hear cheery locals using the word ‘ole’ as a day-to-day expression. It’s time to scribble ‘Jerez’ at the top of your city break list. Hotel YIT Casa Grande has two main selling points: its sprawling, sun-drenched roof terrace and its historic-centre location. It has an old-world British B&B feel, with homely rooms, a cosy ‘chill-out’ area and a small internal patio that’s perfect for breakfast. A charming family-run hotel, La Fonda Barranco prides itself on its excellent service – you can even send WhatsApp messages to the manager. Traditional rooms and a rooftop terrace overlooking the ancient Jerez cathedral add to the hotel’s allure. Just around the corner from the central market, Hotel Dona Blanca is a typically Andalusian three-star hotel that has been in the same family since 1992. Rooms are small but well-finished, some in minimalist style with neutral hues, while others have an English country home feel. Doubles from £46, visit hoteldonablanca.com. Hotel YIT Casa Grande has two main selling points: its sprawling, sun-drenched roof terrace and its historic-centre location. It has an old-world British B&B feel, with homely rooms, a cosy ‘chill-out’ area and a small internal patio that’s perfect for breakfast Like a lot of hotels in Jerez, Hotel Palacio Garvey is set in a 19th-century palace. Its rooms have high ceilings, and there’s an adorable communal patio. But there are only 16 rooms, so book quickly. Doubles from £68, visit hotelpalaciogarvey.com. Start your visit by going on a walking tour with Sherry Tour (freetour.com). It is tip-based, so bring cash – £8.50 to £17 pp is the average. English tours run from Plaza del Arenal, Jerez’s main square, and offer a glimpse into the city’s intriguing past – from its links to the Phoenicians, Arabs and English to its sherry-making heritage. It would be unthinkable to visit Jerez and not do a sherry-tasting tour – Jerez, after all, means sherry in Spanish. Try the one by Lustau (tastings from £16 pp, Monday to Saturday, lustau.es). Information on this tour is easy to digest, and you’ll get to taste six different types of sherry as you wander the shadowy, cool winery. Flamenco runs through the veins of natives here, many of whom claim it originated in Jerez (though Seville, Cordoba and Granada might have something to say about that). Visit Tabanco El Pasaje (tabancoelpasaje.com), a rustic little tabanco. Or try Damajuana (damajuanajerez.com), which hosts flamenco shows in an old palace courtyard. Act like a Jerezano by browsing the Mercado Central de Abastos, the city’s central market. Here, vendors swig cold sherry as locals haggle for meat, fish and vegetables. For an authentic experience, take the first right through the main door and buy yourself a bag of golf ball-sized olives and some jamon, then enjoy them over an ice-cold Cruzcampo beer. Visit Fundacion Real Escuela Andaluza del Arte Ecuestre (£18, realescuela.org) for a proper Jerez experience. Take your seat in the grand auditorium and watch as pristinely groomed horses do elegant can-can kicks to classical music under the expert steer of smartly attired riders. Then drift around the training areas and the Recreo de las Cadenas Palace with its exotic, technicoloured gardens. The Moors left beautiful architectural imprints on lots of Andalusian towns, including Granada (the Alhambra) and Seville (La Giralda), so it is hardly surprising that Jerez has its own ancient Arabic buildings. The most notable is the Alcazar (£4.50), an 11th or 12th-century Almohad fortress, which was heavily restored in the 17th and 18th centuries. Walk around the botanical gardens, see former noblemen’s baths and head up the octagonal watchtower to dine out on city views. This old-school Andalusian restaurant used to be a Jerez favourite (even Jude Law once visited). Its popularity has faded slightly, but it’s still a solid option for affordable, no-nonsense racions (big plates for sharing, from £5). Artichokes cooked in a dry sherry sauce (£9.30) are what Bar Juanito is known for – but they’re an acquired taste. Visit bar-juanito.com. Overlooking the popular Plaza Plateros, making it a worthy place to people-watch over a frosty sherry in the mid-afternoon, tapas and racions here are homecooked, cheap and full of flavour. Try the slow-cooked pig’s cheeks in sherry sauce (£2.70) and paprika squid with potatoes (£12.50 for a big plate). Want something else to go with your sherry? Head next door to delicatessen El Espartero and bring it back to the restaurant – it’s fine, they have an agreement. Address: Plaza Plateros, 3. A five-minute walk from Plaza del Arenal, El Trastero is a no-frills bar and there’s a chance you’ll have to eat tapas the real way – standing up. But the food is exceptional, and the prices are silly cheap. Order the fried shark or red tuna (both £3) and a small glass of Alhambra beer (£1.25). Visit eltrastero-bar.negocio.site. Meat-lovers will relish this open-plan restaurant with exposed brick walls. Try the sharing steak (£15), which comes with a grill to cook it yourself, or the fried pork with potatoes and flaming chorizo (£3). Portions are American in size – you’ve been warned. Address: Calle Remedios, 2. The Spanish love treating themselves to churros at the weekend. Buy yours at this stall, across from the market, then head to Cafe Plaza de Jerez to buy your dipping chocolate – and get stuck in.