A baroque jewel in Italy’s southeastern heel, Lecce flourishes with the carved sandstone of its cathedrals and piazzas. Atmosphere and cuisine are the main attractions here, with rustic Apulian cuisine on offer at the countless wine bars and cafes spilling onto the city's cobblestone lanes.

One of Puglia’s most picturesque enclaves, Ostuni is known as the White City thanks to its plenitude of white-washed houses. A quick trip from the coast, the city is also celebrated for its labyrinthine streets, cathedral, and ancient defensive walls.

A Puglia port town that’s equal parts historic and functional, Monopoli makes a splash with medieval churches and castles jutting above the Adriatic. It’s also a painter’s dream, with bright blue fishing boats adding a pop of colour against whitewashed harbour walls.

It’s nicknamed the Eternal City for a reason. In Rome, you can drink from a street fountain fed by an ancient aqueduct. Or see the same profile on a statue in the Capitoline Museum and the guy making your cappuccino. (Which, of course, you know never to order after 11 am.) Rome is also a city of contrasts—what other place on earth could be home to both the Vatican and La Dolce Vita?

Once known for smog, traffic and tacky architecture, Athens is a city reformed thanks to fortunes brought by the 2004 Summer Olympics. Spotless parks and streets, an ultra-modern metro, new motorways, an accessible airport and all signs in perfect English make the city easily negotiable. Meriting more than a stopover en route to the islands, sophisticated Athens sites include many pillars of Western history, from the Acropolis to the Temple of Olympian Zeus, as well as treasures in the National Archaeological Museum.

Avignon charms visitors with its ancient streets, restored mediaeval ramparts and the immense Gothic architecture of the Palais des Papes (Palace of Popes—the papacy was based here in the 14th century). The annual Festival d'Avignon, a major arts festival, attracts hundreds of thousands of visitors for theatre, dance, film and street performances.

Lisbon, the capital city of Portugal, has become an increasingly popular place to visit in recent years, with a warm Mediterranean climate in spite of its place facing the Atlantic Ocean. Full of bleached white limestone buildings and intimate alleyways, Lisbon's mix of traditional architecture and contemporary culture makes it the perfect place for a family holiday. Things to do in Lisbon: As Portugal's capital, there is a lot to see and do in Lisbon. Even exploring the city centre will take a few days out of a family holiday as there is no real central district, although Praça do Comércio is a good central place to start, in Baxia, or Rossio, the city's main square which has a sort of Trafalgar Square feel to it. Or you might try climbing up the Cristo Rei, a huge statue of Christ with spectacular views across the whole city. The Castelo de São Jorge also offers great views and isn't quite such a steep climb. A short tram ride to the west of Lisbon will also bring you to Belem, where you can explore attractions like the Belem Tower and the Belem Cultural Centre, which features a fantastic art collection including works by Dali, Picasso, Warhol and Magritte. In downtown Lisbon, you'll also want to visit the Gulbenkian, which has to be Portugal's answer to the British Museum full of fascinating cultural artifacts and with some superb gardens in the grounds. It's possible to have a fascinating educational family holiday in Lisbon, and there are also plenty of great beaches to work on your tan.

Dubai is a destination that mixes modern culture with history, adventure with world-class shopping and entertainment. Catch a show at the Dubai Opera, see downtown from atop the Burj Khalifa and spend an afternoon along Dubai Creek exploring the gold, textile and spice souks. If you’re looking for thrills, you can float above the desert dunes in a hot air balloon, climb aboard a high-speed ride at IMG Worlds of Adventure or skydive over the Palm Jumeirah.

Montreal, c’est si bon! This French-speaking city is considered the cultural capital of Canada, and is a cosmopolitan celebration of Québécois style. A horse-drawn carriage ride around the cobblestone streets and grand buildings of Vieux-Montréal will give you a taste of European flavour. The Basilique Notre-Dame is a confection of stained glass, and the Plateau Mont-Royal district will delight you with its quaint boutiques and cafés. Dig in to a massive plate of poutine to fuel up for a tour of the epic Olympic Park.

The first time you go to New York, go ahead and be a sight-seer—everyone should visit the Statue of Liberty, the Met, Times Square, etc. But on a return trip, pick a neighbourhood and go deep. You’ll find hole-in-the-wall bars, great delis, quirky shops… exploring the non-touristy side of New York is an incredibly rewarding experience for a traveller.