Basking in its 300 days of sunshine, Lake Tahoe is a haven for outdoor fun in every season. Swimming, kayaking and windsurfing are popular in the summer months, while epic snowfall makes for spectacular skiing in winter. For those who prefer indoor fun, there's plenty of that in Tahoe, too. With 24-hour casinos and a flashy nightlife scene, the area has a tangible Vegas vibe. A sprinkle of bling, if you will. Not surprising, since Lake Tahoe straddles the border between California and Nevada.

Think picnics on gorgeous, uncrowded beaches, fabulous seafood restaurants, and great hotels overlooking beautiful Monterey Bay… Monterey is a great place for a romantic getaway. Nature buffs can explore the bay by kayak for a close-up look at sea lions, seals and otters.

It's still one of the most British cities in North America, but there's more to Victoria than tearooms, antique shops and galleries (though there are plenty of those). Driven by the younger generation, the city has sprouted a collection of cool shops, authentic coffee bars and unique restaurants. It also has more cycling routes than any other Canadian city, providing a great way to explore the picturesque location (and avoid an afternoon of antique shopping).

Hidden gems of Yucatan, such as Tulum, Akumal, Chetumal, Chichen Itza and Merida, offer an authentic taste of Mexico. Akumal and more Caribbean-style Chetumal, near the Belize border, deliver delectable white-sand beaches and great snorkelling. Merida, Chichen Itza and Tulum, with their ancient ruins, offer a passage into the Yucatan's native history. Nature lovers can jungle trek and swim in subterranean sinkholes filled with crystal-clear water. Bike around the ruins and hop between towns in colectivo vans.

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.

What makes Anguilla's beaches the best in the world? White, powdery sand that stretches for miles, pristine waters and the laid-back, welcoming attitude of the Anguillan people. Swim and sunbathe all day—and all year round—at romantic public beaches like the aptly-named Rendezvous Bay, then dance to calypso music at Anguilla's annual summer festival.