Lecce or Skopje?

This is the widest gap between the two cities. Lecce is a short drive from two seas. The Ionian side has fine, shallow sand at Porto Cesareo and Punta Prosciutto, the Adriatic has pale coves and sea stacks at Torre dell'Orso, and you can swim from June well into October.

Skopje has no beach at all. In summer, swimming means city pools. The reservoir at Matka is cold and better suited to a kayak, and Lake Ohrid needs a stay of its own rather than a day out.

Both cities cook their own regional food well and both lack range, but Lecce's table is the more distinctive. The day runs from pasticciotto and iced almond coffee at breakfast to ciceri e tria and orecchiette at dinner, with Negroamaro and Primitivo from the surrounding plain.

Skopje's food is heartier and simpler: tavche gravche, grilled meat with ajvar, and burek with yoghurt in the morning. The Tikves wines are a real discovery and the long tavern tables of Debar Maalo make dinner an event, but you can work through the whole local menu in a few days.

Lecce has the more rewarding townscape. Its Baroque centre, carved in honey-coloured stone, is almost intact, with Santa Croce, the enclosed Piazza del Duomo and a half-excavated Roman amphitheatre in the main square. The pleasure lies in walking the streets, not in the museums.

Skopje is more uneven but more surprising. Across the Stone Bridge from the statues and replica facades of Skopje 2014 lies the Ottoman Old Bazaar, with its caravanserais and mosques, and the story of the 1963 earthquake runs through the city's museums. It is interesting rather than beautiful, and two or three days covers it.

Neither city is worth travelling to for nights out, and both are sociable rather than loud. In Lecce the evening means the passeggiata, an aperitivo on the piazzas and small wine bars in the lanes. In summer, serious dancing moves out to the coast near Gallipoli.

Skopje's nights run on cafe-bars. The terraces of Debar Maalo move from coffee to rakija as the evening goes on, and weekends are far livelier than weeknights. Its few clubs and the summer parties near the City Park are in town, so getting there takes no drive.

Skopje is much better for walking and mountain air. Mount Vodno rises from the southern suburbs, and Matka Canyon, half an hour away, has kayaking and monasteries on the cliffs. The Sar mountains and Mavrovo add high ridges in summer and skiing in winter.

Lecce's outdoors is the sea and the shore. Inland is a flat plain of olive groves. Along the coast there are cliff paths and sea caves between Roca Vecchia and Otranto, wetlands at Le Cesine and Alimini, and good snorkelling, but no hills.

Lecce has more within easy reach. Otranto's cathedral mosaic, Gallipoli's island old town, the frescoes at Galatina and the stone towns of the Salento are all close. Ostuni and the trulli of Alberobello make longer days out to the north.

Skopje's outings are more spread out: the painted mosque in Tetovo, the Roman ruins at Stobi on the way to the Tikves wineries, the crater town of Kratovo, and Prizren across the border in Kosovo. Its best-known town, Ohrid, is too far for a day trip. In both cities a car makes things far easier.

Lecce is the easier choice with children. The old town is largely free of traffic, the piazzas fill with families in the evening, and the water around Porto Cesareo is shallow and sandy. Days are simple as long as you rest through the summer midday heat.

Skopje's cafes welcome children warmly, and the Vodno cable car and a boat ride at Matka make good outings. Busy roads, uneven pavements and the lack of any beach make longer stays tiring, though. Neither city has much built specifically for children.

Both are easy on foot and awkward beyond the centre. Lecce's centre is flat and partly pedestrian, with the station at its edge and fast trains to Bari. The local railways across the Salento are slow, though, so most visitors hire a car for the coast.

Skopje's sights all lie along a level walk beside the Vardar. There is no metro or tram and the buses are confusing for newcomers, but cheap taxis cover Vodno and Matka, so you only need a car for the mountains and the wine country.

Neither is a shopping destination, and the real difference is in the crafts. Lecce has papier-mâché saints from old-town workshops, small carvings in the local limestone and ceramics from Grottaglie, as well as olive oil and taralli.

Skopje's Old Bazaar sells silver filigree, copperware and embroidery, and Bit Pazar is a proper working market full of spices and cheese. For clothes, Skopje has malls with international chains, while Lecce has a few fashion shops on its main streets.

Skopje is the cheaper of the two by a wide margin, but the bigger difference is how much the calendar matters. In Lecce, the cost of a trip depends on when you go. August, when Italians fill the Salento, coincides with the warmest sea, so rooms and beach clubs charge the most then, and the car most visitors hire comes on top. Come in June or September and the same stay costs noticeably less, and the water is still warm enough to swim.

Skopje has no coast to bring in summer crowds, so it has no real peak, and you can pick your dates by the weather alone. The savings show in the small daily decisions: you can eat out every night without counting, take a cab to Vodno or Matka instead of renting a car, and visit most sights for little or nothing. Even the smarter places along the Vardar don't break a modest budget.

Both cities have a modest formal season and a stronger folk tradition. Lecce comes into its own in summer, when pizzica fills the village festivals and the Notte della Taranta in Melpignano draws a huge crowd in August.

Skopje's programme is steadier through the year. It has a national opera and ballet, the Philharmonic and a long-running autumn jazz festival, and starogradska songs are played in the taverns of Debar Maalo. In both cities, plays are mostly in the local language.

Lecce is the more restful base. The sulphur springs of Santa Cesarea Terme, in grottoes and pools above the sea, are under an hour away, and converted masserie on the plain offer quiet stays with spas.

Skopje's old hamams are now art galleries, not baths, and Katlanovska Banja is a thermal spa with a sanatorium feel rather than a place to be pampered. The city's real calm lies in long hours over coffee on shaded terraces.