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.

Get to Matera quickly, because it’s still relatively undiscovered by foreign tourists. In town, visit the Domenico Ridola National Museum. Matera’s real claim to fame, though, and the reason it’s a UNESCO World Heritage Site, is the extensive series of cave dwellings ("i sassi") southeast of town, first inhabited by Benedictine and Basilian monks. You’ll see individual cells, chapels, and even some churches, many adorned with Byzantine decorations and frescoes.

Gaze out at the azure Adriatic Sea from the sunny beaches of Otranto, in Italy's Puglia region. This historic port town attracts locals and tourists to its 10km of beaches and diving rocks. In town, the cathedral features large-scale mosaics dating back to the 12th century. If you love snorkeling and beautiful seaside views, it's worth making the short journey south to Porto Badisco.

From the heights of the Bay of Fundy tides to the sandy beaches and warm waters of the Acadian coast, New Brunswick is home to spectacular natural wonders and first-class attractions. The Canadian province is also renowned for its outdoor adventures, natural and recreational parks, pristine rivers, lively cities, picturesque towns and vibrant culture. Add a dash of Acadian joie de vivre and its people’s legendary friendliness and you have the makings of a truly unique Maritime experience.

Quebec City may be the only fortified city north of Mexico, but it welcomes visitors with open arms. Explore the Citadel, where you might catch Canadian troops staging a military ceremony. As for food, you could splurge on afternoon tea at the Chateau Frontenac, or do as the locals do and snack on poutine—french fries with gravy and cheese curds.

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.

We won't lie: Niagara Falls is uber-touristy. There are wax museums and a Ripley's Believe It or Not Museum, and if it's a fast-food chain, you can probably find it here. But even the most jaded hipster shouldn't pass up a chance to visit this town, because the Falls themselves are spectacular.

Collingwood is more than just a neighbour of Blue Mountain Ski resort. This town on Nottawasaga Bay has its own delights to discover, from historic homes to parks and trails, a marine heritage museum, and its own annual Elvis Festival.