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In my travels, I’ve found that some of the world’s most unique and intriguing destinations are located on a crossroads or along borders. Places with a history of touching or overlapping cultures tend to be especially complex and rich—think Croatia or the Alsace region of France. But the most exotic and fascinating example of a city at a crossroads is Istanbul. For centuries described as a heady meeting between East and West, Istanbul has served as the capital of three of the greatest empires in Western history and is on the legendary gateway between Europe and Asia. These days, the city is also on the thrilling edge of age-old tradition and high-tech modernity. In some ways, it’s the best of both worlds. On one hand, Istanbul is an impressive example of secular Islam (you might see more women in head scarves in Paris than in central Istanbul), and on the other, it’s a modern Western metropolis, urged on by the drive to join the EU.

Like Rome and Paris (but without as many tourist traps), you can turn almost any corner and be faced with a stunning landscape of the past. Turn another corner and you’re back in the lively present. Istanbul might be old—it was founded as Constantinople in 660 B.C.—but it has the youthful energy of a teenager, which may be why it’s often described as a city full of minarets and miniskirts. One minute you’ll hear the poetic call of the muezzin to prayer, and the next, lounge music from one of the city’s many terrace bars.

For a guide to the Turkish Riviera and suggestions on boat charters, click here.