Named for a local swamp fish, Paraty sits on Brazil's southeastern coast, 125 miles south of Rio, with the Bocaino Mountains at its back. The small colonial town's center is a national historic monument with well-preserved buildings on its pedestrian-only streets. Take a boat trip out into the bay to the flotillas of islands and coves nearby. Explore sugarcane plantations and hike or take a train through Atlantica Forest. Keep an eye out for the monkeys that roam the cobblestone streets.

Situated on the breathtaking Litoral Norte (north shore) of São Paulo state and straddling the Tropic of Capricorn, the town of Ubatuba is a beachcombers' and surfers' paradise. In fact, the city of 78,000 (225 kilometers northeast of the state capital) is known as the Surf Capital of São Paulo, as well as being a major sailing center. Visitors and locals have more than 100 beaches to choose from, so you've got no reason to go home without tan lines. Well, unless...

German-inspired architecture adds a quirky Alpine twist to this resort, where high-altitude pine forests offer a wonderfully cool escape from the lowland heat. Add emerald-green peaks as a backdrop, and Campos do Jordao becomes a tropical mountain stunner.

Among the best golf destinations in the world, Punta Cana is the very picture of leisure. Several of the courses have been designed by professional golfers, making for the perfect sort of kicked-back challenge that you want on a golfing vacation. The beaches here are simply perfect: calm, warm waters that gently lap at stretches of fine white sand. Thrill yourself with a zip-line adventure, clap along with traditional Dominican music at a cultural performance, or explore the magical lagoons of the Indigenous Eyes Ecological Park.

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.

From the Magic Kingdom to magical spa treatments, Orlando sparkles with the promise of adventure. Spend a day exploring the world-famous Disney theme parks or screaming your head off on a Universal Studios roller coaster. For a less adrenaline-pumping afternoon, enjoy the quiet natural beauty of the Harry P. Leu Gardens or enjoy a seaweed scrub at a luxury day spa. Savor fresh and local ingredients at one of Orlando’s James Beard-nominated restaurants.

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.