Enjoy an old-fashioned beach holiday, complete with a boardwalk, at one of Delaware's most popular resort towns. Long a traditional summer getaway for families, Rehoboth Beach is now also a favourite of gay and lesbian travellers. Serious golfers will want to test their skills at the Kings Creek Country Club, while Old Landing Golf Course offers great views of the local scenery. Along with enjoying the famous beach and strolling the boardwalk, there's also a nearby amusement park called Funland to check out.

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.

The Out Islands are synonymous with sport, from the depths of the Gulf Stream that yield big game fish to the coral reefs just off shore that are catnip to scuba divers. Sailing, kayaking and beach-combing add action to lazy days in the sun, while resident pink flamingos and rare Bahama parrots colour local hikes.

Any city that can be the butt of a Simpson's joke ("That's it! We're all going back to Winnipeg!") and simultaneously one of the most vibrant cultural centres in Canada is tops in our book. The city's history of isolation and self-sufficiency means that Winnipeggers are unpretentious and sincere (and fun-loving enough to name Homer an honourary citizen). Though the winters are long and cold, there are plenty of indoor activities to both keep you warm and stimulate your imagination.

Only 21 miles from RDM airport, Bend is a natural playground for families and adventure travellers. Hiking and fishing along the Deschutes river, mountain biking and skiing at Mt. Bachelor are among the favourite activities. Enjoy award-winning restaurants or one of the nearly 30 breweries and pubs. Sunny weather compliments the many world class festivals and concerts. Bend is a great spot for family-friendly fun as well, from the High Desert Museum to ski areas with no fees for children under 12.

What happens when a "gassy" Englishman rows into town feeling thirsty? A pub is born. And from that a city—in this case Vancouver. Though the pubs are plentiful, food and drink aren’t the only things to take in during your trip. In its 150 years, Vancouver has grown into a cosmopolitan city nestled in the great outdoors. Enjoy the snow-capped mountains, waterfront forests, cityside beaches, Olympic history and the world’s highest suspension bridge. Hipsters welcome. (Don’t worry, they don’t bite.)

Portuguese, French and Berber architecture frame the maze-like streets of Essaouira, a charming and vibrant port and resort town on the Atlantic Ocean. Nearby, couples and families stroll the beaches of Cape Sim and Sidi Kaouki, which also attract surfers of all types. Relaxation is easy to find here, as is a bus to Marrakech, for those looking for a daytrip.