Perched on the northern end of Sicily’s less-travelled western coast, Trapani has an old-world Mediterranean soul. Travellers come to see the traditional salt flats and tuna fisheries along its crescent-shaped bay, and to ride a ferry out to the nearby Aegadian Islands.

Mainstream tourists haven’t discovered San Vito lo Capo yet—so if you’re looking for a low-key, authentic Italian beach break, now’s the time to book your trip to this seaside Sicilian town. The weather is best in the summer months, but foodies might want to wait till September, when San Vito lo Capo hosts its annual Couscous Festival.

To the first-time visitor, Palermo is a city of ever-changing character. An abundance of dusty museums, Arabian domes and flourishes of baroque splendor jostle with boisterous markets, chaotic traffic and oppressive summer heat. The Sicilian hotspot is a noisy, polluted, often dangerous, but always fascinating city. Don't miss marvels of Arab-Norman architecture, such as 12th-century Palazzo dei Normanni or San Giovanni degli Eremiti. Ask your hotel to arrange cabs and negotiate fares before setting off.

Thanks to its volcanic history, the island of Ustica offers awesome opportunities for deep diving. Notable sites include Scoglio del Medico and Grotta dei Gamberi. Snorkelers can explore Grotta Azzurra, Grotta Verde, and Grotta delle Barche. There are plenty of dive centres that can offer guided trips to all of these watery hotspots. Once you dry off, check out the prehistoric ruins of a large village that dates to the Bronze Age. Houses in the main square are painted with colourful murals, giving the whole village an artsy vibe.

Though Agrigento is a modern city of about 60,000 on Sicily’s southwest coast, the majority of visitors come to experience the past just outside of town. At the Valley of the Temples (Valle dei Templi), citizens of the then-major Greek colony of Akragras began building seven Doric style holy monuments in the sixth century BC. The nearby Archaeological Museum helps put everything into context. Agrigento also has some fascinating sights in its old town, like the medieval Norman cathedral.

The oldest university in the world isn’t Oxford or the Sorbonne—it’s the University of Al-Karaouine, and you’ll find it in Fes el Bali. This walled city, a UNESCO World Heritage Site, will transport you back to mediaeval times. Visit the ancient maze-like quarters of the Medina to Fes el-Bali and the four imposing Gates of Fes, with their distinctive Moroccan tile work. You can walk, or, if you're brave, take a taxi—the daredevil drivers will have you hanging on for dear life.

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.

Ottawa is a compact, clean, cleverly planned centre of culture and politics. And it's an ideal choice for a weekend getaway. Start downtown at the architecturally stunning National Gallery of Canada, and don't miss the Canadian Nature Museum and the National Aviation Museum. Rideau Canal offers boating in the summer and ice-skating in the winter. Gatineau Park attracts cyclists and walkers, while Byward Market blends old and new Ottawa.

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.

We've heard Toronto described as "New York City run by the Swiss," and it's true—you can find world-class theatre, shopping and restaurants here, but the sidewalks are clean and the people are friendly. The best place to start is literally at the top—the CN Tower, the tallest freestanding structure in the Western Hemisphere.

Toronto's neighbour Mississauga has more than 480 parks and woodlands for you to explore. Stroll the Waterfront Trail, rent a boat at the marina or spend a day at the racetrack. It's also called Ontario's shopping capital, with everything from shopping centres and outlet malls to picturesque village-style shopping streets.