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.

A patchwork of vineyards and olive groves, dotted with whitewashed hill towns and sun-bronzed beaches—Italy’s southern heel has no shortage of photogenic landscapes. There are a few surprises, too, including the baroque city of Lecce and the Itria Valley, with its UNESCO-listed trulli houses.

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?

Founded by the Romans in 179 AD as Casta Regina (meaning Fortress by the River Regen), Regensburg is one of Germany's oldest towns. It was relatively spared from Allied bombings during World War II. Today, many flock to see the wonderfully intact old city and its many medieval structures. The 12th-century Stone Bridge was used by Crusaders en route to the Holy Land. The Regensburg Cathedral (or Dom St. Peter) is one of southern Germany's finest examples of Gothic architecture.

Everyone who visits Paris for the first time probably has the same punchlist of major attractions to hit: The Louvre, Notre Dame, The Eiffel Tower, etc. Just make sure you leave some time to wander the city’s grand boulevards and eat in as many cafes, bistros and brasseries as possible. And don’t forget the shopping—whether your tastes run to Louis Vuitton or Les Puces (the flea market), you can find it here.

From Shoreditch’s swaggering style to Camden’s punky vibe and chic Portobello Road, London is many worlds in one. The city’s energy means that no two days are the same. Explore royal or historic sites, tick off landmarks from your bucket list, eat and drink in exclusive Michelin-starred restaurants, enjoy a pint in a traditional pub, or get lost down winding cobbled streets and see what you stumble across – when it comes to London, the possibilities are endless.

Looking out over the city of St. John's, you may be reminded of a mini San Francisco (minus the cable cars). St. John's provides the ideal balance between nature and nightlife, from the East Coast Trail and its stunning scenery to the colourful entertainment district along George Street. Although it's the largest city in Newfoundland, the vibe is still very small-town. You'll feel welcome in the City of Legends!

Anne of Green Gables! There, we got that out of the way. Besides chasing the famous fictional heroine, you'll find Charlottetown's own history, culture and nightlife keep you more than busy. Enjoy outdoor activities from golfing to boardwalk strolls and biking by day, and theatre and performance arts by night.

travellers say Halifax is best seen on foot, so park the car and start walking. Immerse yourself in Halifax's rich history at the Maritime Museum of the Atlantic, and be sure to survey the city from the 18th-century Citadel National Historic Site. Then walk into any of Halifax's great bars and restaurants and catch some live music to round out your day.

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.