Jerez de la Frontera or Segovia?

Here the gap is as wide as it gets. Jerez has no sand of its own, but the Costa de la Luz is close. Valdelagrana and El Puerto are a short trip, Cádiz with La Caleta is about half an hour by train, and the broad beaches of Sanlúcar and La Barrosa are within an hour. Expect Atlantic water and the odd windy Levante day rather than a calm Mediterranean.

Segovia sits on the Castilian plateau, far from any coast. Swimming there means a hotel or municipal pool, or a cold dip in a Guadarrama reservoir, so beach days have to happen somewhere else on the trip.

Both cities stick closely to their regional cooking, but Jerez has more depth. Sherry runs through everything, from bodega tastings to tabancos pouring fino from the barrel with chacina. The nearby coast adds fried fish and prawns to the berza stew and the oxtail cooked in sherry.

Segovia's food centres on the wood-fired oven, and cochinillo and lechazo are the reason to book lunch, with judiones from La Granja and ponche to finish. That makes for a memorable meal or two, but the choice narrows quickly beyond the roasts, and the asadores by the aqueduct fill with tour groups at midday.

The old centre of Jerez is a pleasant place to wander, with the Almohad Alcázar, the cathedral and the Gothic-Mudéjar parish churches. It also has two things found nowhere else: the cathedral-like sherry bodegas and the Royal Andalusian School of Equestrian Art. Beyond those, the list is modest.

Segovia's monuments are on another level. The Roman aqueduct alone is worth the journey. The walk from it up to the cathedral and the Alcázar at the tip of the ridge passes Romanesque churches with arcaded porches, the old Jewish quarter and the walls, all within the UNESCO-listed old town.

Neither is a clubbing city, but Jerez stays out later. Its tabancos, copa bars and terraces around Plaza del Arenal and Calle Larga keep going past midnight at weekends. During the Feria del Caballo in May the fairground parties until dawn for a week, and El Puerto is close for summer nights by the sea.

An evening in Segovia means a tapas crawl around Plaza Mayor, plus a few student bars at weekends, and the old town goes quiet early in winter. For a real late night, Madrid is the place to go.

Right around Jerez the country is gentle, rolling vineyards on white albariza soil, and the bigger landscapes take a drive. The gorges of Grazalema are over an hour east, Doñana is reached by boat from Sanlúcar, and the salt marshes on the Bay of Cádiz are good for birds. Jerez also has kitesurfing on the coast towards Tarifa and easy horse riding, but the summer heat limits hiking to spring and autumn.

Segovia has the mountains on its doorstep, which gives it the edge. The pine forests of Valsaín and the passes of Navacerrada and Cotos are within half an hour, with trails towards Peñalara and its glacial lakes. There is snow in winter, and an easy path runs along the Eresma valley right below the Alcázar.

Both make excellent bases, so the real question is which part of Spain you want to see. From Jerez it is the south: Seville about an hour away by train, ancient Cádiz half an hour away, and the sherry towns of El Puerto and Sanlúcar. With a car you can reach the white towns, from Arcos to Ronda.

From Segovia it is the Castilian heartland. The palace and gardens of La Granja are twenty minutes away, and Madrid and Valladolid are quick by high-speed train. Walled Ávila, the medieval villages of Pedraza and Sepúlveda, and El Escorial across the mountains are all within reach.

Jerez is the easier of the two with children. In summer there are wide beaches of gently shelving sand, the zoo and botanical garden is among the better ones in Spain, and the dancing horses at the equestrian school usually go down well. The flat centre is easy with a pushchair, though July and August are very hot.

Segovia has the best single treat for children: a turreted cliff-top castle with a tower to climb, plus the giant arches of the aqueduct. Beyond those there is little aimed at children, and the steep cobbles are hard going with small wheels, so a day or two is the right length.

In both cities you can walk to the sights and barely need transport. The centre of Jerez is flat, with the station close by and the airport a few minutes away by train. Segovia's sights line one narrow ridge of steep cobbles, and its high-speed station lies several kilometres out, a bus ride from town.

In both, a hired car makes the surrounding country much easier to reach: the white towns and Grazalema from Jerez, and Pedraza, Sepúlveda and the sierra trailheads from Segovia.

The best things to buy in Jerez come from its horse and sherry traditions. Long-standing craftsmen make saddlery, harness and leather riding boots, and the bodegas sell sherry and brandy at the source. Shops near the old quarters add flamenco dresses, shawls and guitars, while Calle Larga covers the everyday with Spanish chains and older family shops.

Segovia has less to take home. Calle Real is lined with souvenir stalls, and a few shops sell local ceramics, embroidery, boxed ponche and La Granja beans. For fashion or design, people head to Madrid.

Jerez makes a budget go a little further. Sherry and tapas in the tabancos cost little, bodega tours are inexpensive and almost everything is within walking distance. Rooms become scarce and dear during the Feria, the flamenco festival and the motorcycle race weekends.

Segovia is moderately priced too, with plenty of small family-run guesthouses and fair lunch menus in the newer town. The famous roasts are an expensive meal, though, and rooms in the old town cost more at weekends and in summer, when visitors arrive from Madrid. Midweek in winter it is cheap.

This is one of the sharpest differences between the two. Jerez is one of the birthplaces of flamenco. You can hear it close up in the peñas of Santiago and San Miguel and in informal tabanco sessions, or see more polished shows in the tablaos. The late-winter festival at the Teatro Villamarta draws major dancers and students from around the world.

Segovia's live arts come with its festivals: the Titirimundi puppet festival in spring, summer concerts in churches and palace gardens, and touring shows at the Teatro Juan Bravo. Between festivals, little is on.

An Arab-style bathhouse in the old town gives Jerez somewhere to soak, with warm pools and massage, and a few hotel spas add to it. The rest of its calm comes from the southern day itself: long lunches, a quiet afternoon and shaded patios. It is at its best in spring and autumn, when the heat eases.

Segovia has no baths, only a handful of hotel spas. What it offers instead is the hush after the day coaches leave, with evening walks along the walls and pine-scented air coming down from the sierra.