Southwest of Seville, Jerez is a well-heeled place. It’s the home of the Royal Andalusian School of Equestrian Art and its famous dancing horses; if you’re on a budget or can’t be there for a formal performance, it’s worth dropping in to catch a morning training session. The other major reason to visit Jerez is to sample its most famous product—sherry. You can do this at a number of bodegas associated with the world’s best-known brands, including Bodegas Tio Pepe, The House of Sandeman, Jerez, and Pedro Domecq. They’ll soon have you knowing your amontillado from your oloroso. There’s also an Alcázar, dating back to the time of the Almohads, which features a small mosque, now the chapel of Santa María Real.

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.

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.

Originally founded as a Roman city and now home to three UNESCO World Heritage Sites, Seville is bursting with antique charm. The Alcazar palace complex is a stunning collage of architectural styles, and the Cathedral will impress you with its beauty and its status as the burial site of Christopher Columbus. The Metropol Parasol is the world’s largest wooden structure, a massive mix of grids and swirls that contains a market and a terrace observatory.

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.

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.

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?

There are no two identical Bahamas holidays. With options as diverse as its 700 islands, the Bahamas may seem schizophrenic: is it a family destination, a place for lovers to sneak away, a gambling mecca, a cruise-afficianado’s chief port of call or a shopper’s world market? The answer is, yes. It’s that, too.

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.

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 is a melting pot of African, Asian, European and Middle Eastern cultures. You'll experience this diversity in its strong crafts tradition, performing arts and distinctive dining options, like ackee and saltfish with roast breadfruit. Take your holiday to new heights at famed cliff jumping spot, Negril Cliffs. Jamaica offers long beaches, protected coves, rugged mountains, waterfalls, caves and sunshine and chances to play in the surf, ride horses and swim with dolphins. Jump in!

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.