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.

Santo Domingo, the capital of the Dominican Republic and a UNESCO world heritage site, is the oldest continuously inhabited European settlement in the Americas and one of the most populous cities in the Caribbean. The city is a mix of old world charm and modern Latin flair. Its medieval palaces and fortresses mix with nightlife and shopping to rival any modern city in the world. You'll find pristine beaches and hidden gems like a salsa/merengue club set inside a huge underground cave.

What makes Anguilla's beaches the best in the world? White, powdery sand that stretches for miles, pristine waters and the laid-back, welcoming attitude of the Anguillan people. Swim and sunbathe all day—and all year round—at romantic public beaches like the aptly-named Rendezvous Bay, then dance to calypso music at Anguilla's annual summer festival.

Amsterdam is truly a biker’s city, although pedaling along the labyrinthine streets can get a little chaotic. Stick to walking and you won’t be disappointed. The gentle canals make a perfect backdrop for exploring the Jordaan and Rembrandtplein square. Pop into the Red Light District if you must—if only so you can say you’ve been there. The Anne Frank House is one of the most moving experiences a traveller can have, and the Van Gogh Museum boasts a sensational collection of works.