An exclusive resort town long recognised for attracting royalty, Estoril lies less than 20 miles west of Lisbon and is probably best known for its casino. One of Europe’s largest, it was the inspiration for the first of Ian Fleming’s James Bond books, "Casino Royale." Estoril’s mild winters and warm sunny summers make it a perfect beach town, with one of the nicest, Praia do Tamariz, lying right next to the casino. So famous has Estoril become that the local coast is now called Costa do Estoril.

A coastal town just 20 miles west of Lisbon, Cascais was once a small fishing village, but its idyllic scenery attracted the attention of artists, writers and expelled European nobility in the 20th century. Today, it still attracts high society, but all society comes in force to enjoy the gorgeous beaches and adventure options like sailing and surfing. The Conde de Castro Guimarães Museum, a former palace, is now open to the public and displays an impressive collection of art and artifacts.

When 13th-century Portuguese Queen Isabel passed through Obidos and marveled at its beauty, her husband King Denis I simply gave it to her. For centuries after, the kings of Portugal followed suit, presenting the picturesque little town to their queens as a wedding gift. With its white buildings shining as brightly now as then, the walled city of Obidos is very popular with tourists, its hillside location offering amazing views of the Estremadura area. The medieval castle is a main attraction.

Nazare, named after the Biblical “Nazareth” in the 4th century, is Portugal’s most famous fishing village, now becoming important as well in the world of big wave, tow-in surfing. The tallest wave ever recorded being surfed – by a Hawaiian big-wave surfer – was off Nazare.

Time seems to stand still in Evora, a well-preserved medieval town that features protective walls, a 13th-century cathedral, several palaces,and a 1st-century Roman temple. No surprise that the town center is a UNESCO World Heritage Site. Even though it’s kind of creepy, don’t miss the Chapel of Bones, where the remains of nuns and monks are arranged in a haunting mosaic.

Stroll Las Ramblas and enjoy Barcelona's unique blend of Catalan culture, distinctive architecture, lively nightlife and trendy, stylish hotels. You'll find Europe's best-preserved Gothic Quarter here, as well as amazing architectural works by Gaudi. La Sagrada Familia, considered Gaudi's masterpiece, is still under construction (your entrance fee helps to fund the project). Feel like a picnic? Look no further than the rambunctious La Boqueria market, where you can stock up on local delicacies.

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.

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.

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.

If you’re a history buff and a die-hard foodie, Chicago’s your kind of town. Take an architectural-history walking tour, then dine at Alinea (the most celebrated molecular-gastronomy restaurant in the U.S.). And don’t miss the Museum of Science and Industry, the biggest science museum in the Western Hemisphere.

Whether you're into sport, sunshine or salsa, Miami sizzles all year round with exciting entertainment venues and attractions, world-class hotels and restaurants, great beaches and a nightlife that never sleeps. While South Beach, with its hip nightclubs and pastel-hued buildings, gets all the press, other sections of Miami are just as hot and offer culture, recreation and more. Spend the day soaking in the sights and sounds of Little Havana or soaking up the rays at Haulover Beach Park. Explore the Art Deco District or take the children to the zoo. At the end of the day, chill out at one of the area's bars and nightclubs. In Miami at night, the day is just beginning.

With live music to be heard all across town, 24/7, 365 days a year, Music City lives up to its name. From honky-tonk bands jamming at Tootsie’s Orchid Lounge to songwriters in the round at the Bluebird Cafe and country music legends rocking the Grand Ole Opry, you never know who you might see. The creative spirit from Nashville's music landscape flows into the area's myriad art galleries, up-and-coming fashion scene, historic landmarks and chef-driven restaurants.