On the southern tip of Spain and approximately 305 mi/490 km southwest of Madrid, the port city of Cadiz (pronounced CA-deeth) has been active since 1100 BC. During the days of the Roman Empire, its dancers were famous throughout the Mediterranean region. In the 18th century, Cadiz monopolized trade between Spain and America, and wealth was poured into its crowded-but-impressive town houses and gold-domed cathedral.

Today you can enjoy its two beaches, fortifications, seafront avenues and the salty air of its maritime history. The city is also a departure point for ferry boats to the Canary Islands. Cadiz has the liveliest Carnival celebration in mainland Spain. We suggest a maximum of one night.

A bit down the road, on the southernmost tip of the Iberian Peninsula, is Tarifa, the windsurfing capital of Europe. Winds blow virtually every day of the year—trees have difficulty growing, but thousands of windsurfers love it. Tarifa is also an easy jumping-off point to Morocco. High-speed ferries make the round-trip to Tangier daily (try to reserve tickets ahead of time).

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