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.

Travelers come to this small island north of mainland Cuba to bask in the sun, swim in sparkling blue water, and be pampered at an all-inclusive resort. To explore Cuban culture, you’ll need to go farther afield (this is a planned resort development; employees are bused in), but if you’re simply looking for a stress-free tropical break, Cayo Santa Maria might be perfect for you.

Cuba's top beach destination sits on a 13-mile-long peninsula with powder soft sands lapped by waters of the Kawama Channel. Resort hotels teem along the shore that U.S. celebrities and gangsters, including Capone, discovered in the 1920s. Clubs and bars provide mojitos and merriment, after long days baking on the beach, golfing, diving or deep sea fishing. Rent a scooter or hop aboard an open-air tourist train or bus to see more of this stunning spot. Caves, keys and virgin forest add to the area's allure.

Home to palm-lined beaches, tranquil coral reefs, and several top-tier hotels, it’s no wonder why Bavaro is one of the Dominican Republic’s most popular destinations. This resort hub combines convenience and Caribbean culture with an impressive range of activities across its expansive coastline.

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.

Refer to Vancouver Island as Victoria Island and risk a chorus of eye-rolls from the otherwise-friendly locals. Yes, Victoria is the main city on the island, but there are many distinct flavours to its logging and fishing settlements. Food and wine enthusiasts flock to the Comox Valley farm region, while the more outdoorsy types get their fix along the remote, forested beaches of North Vancouver Island. Visit the UNESCO Biosphere Reserve at Clayoquot Sound and you’ll return full of cocktail-party factoids.

The Algarve's sunny shores offer perfect escapes for all types, from those seeking the hot nightlife of flashy, energetic Lagos to those desiring secluded stays in rambling Sagres. Portugal's most southerly region offers historical attractions in former Moorish capital Silves and fascinating Tavira, great golf, fabulous beaches from Praia da Luz to Armacao de Pera, thermal springs at Caldas de Monchique, and miles of limestone caves and grottoes, cliffs and bays along its rugged coastline.