The past runs deep in Cadiz, where cobbled medieval streets spill out into whitewashed Spanish plazas and Roman ruins. As one of Europe’s oldest cities, it has the feel of an urban island, marked almost entirely by beaches and ultramarine harbours dotted with fishing boats.

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.

There are beaches for everyone on Paros—families, partiers, watersports enthusiasts, honeymooners. Anyone can find their perfect stretch of golden sand. The same breeze that rustles orange and pomegranate trees will power your kitesurfing or windsurfing session. In the capital city of Parikia, make sure to pay your respects at the Byzantine “church of 100 doors” (Panagia Ekatontapillani) and visit the seaside ruins of a medieval castle built from the marble remains of an ancient temple.

What makes Anguilla's beaches the best in the world? White, powdery sand that stretches for miles, pristine waters and the laid-back, welcoming attitude of the Anguillan people. Swim and sunbathe all day—and all year round—at romantic public beaches like the aptly-named Rendezvous Bay, then dance to calypso music at Anguilla's annual summer festival.

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?

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.

Guardalavaca, a coastal paradise on Cuba's northern shore, promises an array of adventures for tourists of all stripes.  You can tranquilly explore the countryside on horseback, take a speedboat across the Bahia de Naranjo to the Dolphinarium, or spend a full day on the Beautiful Bariay Jeep Tour, which includes a trip to a local village where you'll visit a doctor's house, a school, and a ration shop. 

Set in rugged, mountainous territory in the east, Cuba's fourth largest city is known as the City of Parks. Columbus called the area the most beautiful land eyes have ever seen and much of the surrounding area hasn't changed. Officially called San Isidro de Holguin, the city's elegant plazas, scatter of colonial buildings and few museums make for a pleasant daytrip. More wonders lie offshore. Swim with dolphins in Bahia de Naranjo Nature Park. Dive to sites off Playa Esmeralda and Guardalavaca.

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.