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.

Home to Windsor Castle, the second residence of Queen Elizabeth II, Windsor is a popular day-trip destination from London. Those who tarry in the riverside town fill their time wandering the cobbled streets, popping in and out of the luxe boutiques, restaurants, and tea shops that tumble down toward the Thames River.

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.

Lying in south central Turkey, the moonscaped region of Cappadocia, southeast of Ankara, is most famous for unique geological features called fairy chimneys. The large, cone-like formations were created over time by erosion of the relatively soft volcanic ash around them. Past cultures have dug into them to create dwellings, castles (like Uchisar) and even entire underground cities like Kaymakli and Derinkuyu, used as hiding places by early Christians. Nearby Kayseri is the gateway to the area.

Cape Ann, just 30 miles from Boston Logan Airport, includes four communities: Gloucester, Rockport, Essex and Manchester-by-the-Sea. The picturesque area that spans the coastline was founded by Pilgrims in 1623 who named it after England's Queen Anne. Today, it's home to fishermen and artists, merchants and writers.

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 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.