Antigua has hundreds of beaches, from the bustling Pigeon Point to the kitesurfing paradise of Jabberwock Beach. It's fun to mix it up—a day spent in a secluded cove, another spent people-watching at a tourist magnet. When you’re tired of sun and sand you can shoot ‘em up at Reservoir Range, where archery and air pistols are a fun way to work out any lingering pre-holiday stress. A tour of the Antigua Distillery is a spirited way to experience a true taste of the island.

Lively Antigua and Barbuda move to the music of steel drums. You can visit a different beach each day and not repeat yourself for a full year—and that's why tourists and celebrities alike flock to this sun-soaked Caribbean island. Take a day cruise, rent some diving gear or cruise up the beach on a Segway for a real adventure, island-style.

In St. John's, the capital city of Antigua, farmers markets, candy- colored architecture and the ruins of sugar plantations vie for attention with a kaleidoscope of coral reefs and sailing adventures. Salute the white baroque towers of St. John's Cathedral that dominate the skyline before joining the flocks of cruise passengers on a Heritage Quay shopping excursion. To experience the island's early cultures, visit the Museum of Antigua and Barbuda, housed in a 1750s colonial courthouse.

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?

Visit Aruba once and you'll instantly start planning your next visit. The island wins you over with gorgeous weather, serene beaches, exciting land and sea activities (ATVs in the outback, anyone?), and terrific nightlife, from restaurants to casinos and nightclubs. Don't miss the live music scene, featuring Aruba's own Tumba music.

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.

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.

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.

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.