Malaga, Pablo Picasso's birthplace and the gateway to the Costa del Sol, is a hectic, sometimes unruly city of 550,000. An impressive number of museums and monuments, including the 11th-century Alcazaba fort and Museu Picasso Malaga, provide plenty of diversions for those who opt not to spend all their time on the coast's famed beaches and in their accompanying bars. The old city bustles with taverns and bistros. The generous Paseo del Parque offers a delightful stroll past banana trees and fountains.

The pristine white beaches of Tarifa are just as majestic as the 800-year-old castle that stands proudly in this southern Spanish town. Windsurfing or kitesurfing is an absolute must, and the sea sparkles with the promise of bustling marine life—perfect for enthusiastic scuba divers. At night, Tarifa itself sparkles with bars, nightclubs and tapas bars galore.

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 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.

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.

If you’re into eating locally and supporting sustainable agriculture, go to Ashville—and eat, eat, eat. This town of less than 100,000 people has 17 farmers’ markets, and the local restaurant scene is all about taking advantage of the seasonal produce sold there. And don’t miss the area’s microbreweries.