The largest island along Brazil's coast and, literally, a “beautiful island,” Ilhabela offers visitors almost 40 kilometres of pristine beaches and a tropical island's worth of hiking trails, waterfalls and even a nascent party scene. At 207 kilometres from the city of São Paulo, Ilhabela can get crowded, so try to get your beach time in during the work week.

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...

Perched on an island a mere 95 kilometers from the city of São Paulo, this bustling beach town seems a world away from the gargantuan urbanity of the state capital. Among its charms, Guarujá counts 23 separate, stunning beaches, all ripe for swimming, sunning and surfing. Families head to the beach at Enseada; singles, it's all about you at Pernambuco.

Although it's also the location of the Latin America's largest seaport, Santos isn't just a boring port town. The city of 420,000, just 75 kilometers from São Paulo, features a seven-kilometer stretch of beach divided into just as many social cliques as you'd find on Ipanema. A verdant promenade separates the beach from the seafront condos and hotels, along which families and friends walk, amble, bike, skate, rollerblade, throw frisbees, you name it. Less sandy points of interest include the Museu do Café Brasileiro (Brazilian Coffee Museum), the Aquário Municipal (City Aquarium), the Orquidário Municipal (City Orchid Garden) and the Neo-Gothic Santos Cathedral.

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?

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.

Cayo Coco, an island just north of mainland Cuba, has some of the world’s most gorgeous beaches—think superfine white sand and shallow, clear water. It’s popular with European travelers seeking a sunny escape at one of the island’s beach-side resorts. Snorkeling and diving are fantastic.

At the shore in Miami Beach, visitors can swim, surf and jet ski in the warm and crystal-clear Atlantic waters. You can also nap on the white sands, work on a tan or simply watch the beautiful people, especially at South Beach, a favourite of models and celebrities.

Myrtle Beach is a family-friendly beach destination—which means in addition to great beaches, there’s plenty to do when the kids are sick of making sand castles. Amusement parks, water sports and golf courses are nearby. And family-friendly dining and hotels abound.

The landscape that inspired Anne of Green Gables entices legions of lovers to Canada’s smallest province. Peaceful P.E.I. is a slow paced haven, full of distinctively Maritime delights. Red sandstone cliffs rise above gentle beaches. Lonely lighthouses dot rocky bluffs. Deserted trails beckon for romantic roaming.