The Okanagan Valley, in the interior of British Columbia, is a popular Canadian vacation destination known for skiing in the winter and watersports in the summer. The area's quaint towns and lush vineyards are connected by a network of clear blue lakes and rivers and surrounded by rolling, sun-dappled hills. Head to Kelowna for one of several wine festivals or to Penticton for the sugary summer Peach Festival. To the south is Osoyoos, home to an arid desert filled with rare plants and animals.

Nestled between the Okanagan Lake to the north and Skaha Lake to the south, Penticton is a vibrant Rocky Mountain city offering no shortage of things to do, from hiking or biking the Kettle Valley Trail to skiing Apex Mountain to climbing the Skaha Bluffs. For a more relaxed vacation, Penticton boasts 28 golf courses, including 7 championship courses, and is home to 88 wineries and plenty of fruit orchards. Join residents in celebrating the annual harvest at the wildly popular Peach Festival.

Although perhaps less flashy than its southern Okanagan neighbors Kelowna and Penticton, Vernon is a year round getaway offering an abundance of fun attractions from sunny beaches and golf courses in the summer to powdery ski slopes in the winter. The area's back country trails provide great exploration points, whether by bike, horseback riding, hiking, snowshoeing or snowmobiling. The pristine scenery of the Rockies surrounds the valley's plentiful vineyards.

Boasting rolling hills, two converging rivers, 82 parks, a sparkling lake and world class sporting facilities, Kamloops is a paradise for the active traveler. One of Canada's sunniest destinations, Kamloops enjoys on average over 2000 hours of sunshine a year and makes the perfect spot for a round of golf, a rugged bike ride through the hills or an exhilarating excursion to nearby downhill or cross country skiing facilities.

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.)

Toronto's neighbour Mississauga has more than 480 parks and woodlands for you to explore. Stroll the Waterfront Trail, rent a boat at the marina or spend a day at the racetrack. It's also called Ontario's shopping capital, with everything from shopping centres and outlet malls to picturesque village-style shopping streets.

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.

Known for its markets and its striking 19th-century limestone architecture, Kingston is a great base for exploring the Thousand Islands and the St. Lawrence River and its national park. Visit Wolfe Island on the free ferry, or hunt for antiques in nearby villages.

It’s not just for spring-breakers. Cancun, with its golden beaches and perfect climate, is the premiere coastal destination in Mexico. And while there is certainly a 365-day party available for college students, resorts cater well to families and to those seeking solitude. This Yucatan paradise is also the gateway to the ruins of Tulum and Chichén Itzá.

Stretching from the fishing village of Puerto Morelos to the biosphere reserve of Sian Ka'an, the Mayan Riviera offers an unforgettable Caribbean coastline experience. Divers and snorkelers will be dazzled by the wrecks of Xcaret and the Puerto Morelos reef. Use a zip line to descend into the sacred subterranean caverns of LabnaHa Eco Park, where you can snorkel an underground river under a canopy of stalactites. The nearby Tulum Monkey Sanctuary will put you in a playful mood.

Tulum is relaxation and romance with an ancient angle. Guests can enjoy modern takes on traditional Mayan massage and spa treatments, or sunbathe on gorgeous Yucatan beaches within site of well-preserved ancient ruins. A rare mix of beach, archeology and village, Tulum is a romantic getaway like no other.

Immortalized by Hemingway in “Islands in the Stream,” Cayo Guillermo is perched on Cuba’s north coast between the Bay of Dogs and the Atlantic. It is home to four all-inclusive resorts. Five miles of fine white sand and gorgeous, clear green waters, including the spectacular Playa Pilar, offer picture perfect sunning spots. Fantastic snorkeling and scuba diving opportunities beckon from more than six miles of coral reefs. Flamingos and many other birds live in its lagoons, forest and jungle.

U.S. citizens still need to jump through a few hoops to visit Cuba, but as visitors from around the world know, this island offers some amazing opportunities for cultural exchange. Havana is a mix of old-world architecture and of-the-moment culture. Head out of the capital city to the small town of Trinidad to see more Spanish colonial architecture. It’s a UNESCO World Heritage Site and a fantastic home base for a visit to the Valley of the Sugar Mills, a pocket of land that formerly served as the centre of Cuba’s sugar industry.

The Dominican Republic lies in the same waters as Cuba and Puerto Rico, taking up the eastern two-thirds of the island it shares with Haiti. Offering a lush interior with a mix of caves, Victorian gingerbread houses and the lore of pirates, plus 900 miles of coastline along its brim, island highlights include riding a cable car up Mount Isabel de Torres and basking on stunning Saona Island. Oh, and did we mention the D.R. is family-friendly, has just about perfect weather and is affordable?