Located on the Strait of Gibraltar where Africa meets Europe, Tangier has long held strategic importance. Ruled through the centuries by waves of conquerors including Romans, Vandals, Byzantines, Arabs and Portuguese, the city is more than two and a half millennia old, making it one of North Africa's most ancient. The medina, kasbah, bazaars and souks are among the country's most vibrant, and the beaches are excellent. In the last century, Tangier became a hot spot for the international jet set.

Unlike many of its coastal neighbours, cultural tradition remains strong in Estepona. With more than 12 miles (20 kilometres) of palm-fringed coastline and a historic old town famously decorated with bright blooms, this harbour town is undoubtedly one of the prettiest on Spain’s Costa del Sol.

The Costa del Sol juxtaposes gorgeous Mediterranean old towns and inland national parks with developed beach resorts. Famed for being the birthplace of Picasso, Malaga serves as a gateway to family-favourite stops such as Benidorm and Fuengirola.

In the chic, sun-drenched Costa del Sol town of Marbella, hints of its former Moorish occupation mingle with modern-day resort amenities. Bask on the sands of famous La Fontanilla beach or ricochet among the area's family-oriented water, wildlife and theme parks. Experience the Andalusian charm of the historic quarter, filled with whitewashed buildings, remnants of a ninth-century Arab fortress and fragrant orange trees. End a relaxing day with a dish of the cold almond soup ajoblanco and some of the region's excellent dessert wine.

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.

More than 60 idyllic islands, including Jost Van Dyke, Tortola, Anegada and Virgin Gorda, make up the BVI. Turquoise waters offer thrilling diving, fishing, sailing and swimming. Tortola is the largest island in the volcanic chain and has beautiful beaches and coves, forts, ruins and warm, welcoming people. Virgin Gorda boasts yacht clubs, chic resorts and secluded sands. Coconut palms shade beaches on tiny Jost van Dyke. Sailing is a popular way to travel between islands. Ferries are the other option.

The Turks and Caicos offer the best of the Caribbean - in Atlantic waters. Hop between the islands by ferry or explore an island on a hired bike or scooter. One of the world's longest coral reefs, 230 miles of white sandy beaches, crystal-clear waters and an abundance of dive spots lure visitors to the Turks and Caicos' eight major islands, just east of the Bahamas. Bird sanctuary French Cay, underwater Columbus Landfall National Park and Caicos Conch Farm are among the major attractions of these legendarily friendly isles.

Lively nightclubs pulsing with Caribbean beats drive the nightlife scene of Cabarate, a breathtaking beach town. Not even the stubbornly two-left-footed can keep their toes from tapping when the sun goes down on Cabarete, which brims with culture and energy. Beachfront bars cum discotheques are the perfect spot to shake what your Mami gave you.

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.

Jamaica’s most energetic city, Montego Bay is both a raucous spring-break party town and a destination for those seeking a more low-key adventure. Known equally for its duty-free shopping, clear-water snorkeling, diverse nightlife and natural beauty, Montego Bay makes for a perfect Jamaican weekend getaway.

Just north of Cancun, this seaside resort community is a far cry from the spring-break crowd. Bordered on one side by the Mexican Caribbean and the other by a wetlands wildlife preserve, the vibe in Playa Mujeres is one of laid-back luxury in a natural, untouched landscape. Unlike many other such tranquil places, Playa Mujeres is not a pain to get to. It's an easy ride from Cancun airport.