Begin and end your journey where Old World meets New, in historic San Juan, littered with more than 400 restored Spanish colonial buildings. As you continue on this bewitching Caribbean cruise through the Virgin Islands, no two days are alike. One day, you’re shopping chic French boutiques for the latest fashions from Paris. On another, snorkeling a secluded cove known only to lucky yachtsmen – like you. Skip more common and commercial ports in favor of less-visited destinations like Montserrat.

Set a course for hidden harbors and the delights of off the beaten path Greece during a seven-day cruise to Hellenistic islands and a moonlight dinner concert in the Turkish ruins of Ephesus. Explore the colorful interior of the Cathedral of St. George atop Syros, a stately, hillside landmark founded in the 1200s and continually restored after devastating battles. Listen as a moonlight concert reverberates across the ancient Celsus Library walls during your candlelight dinner in Ephesus.

Discover a different side of the Mediterranean this winter, one where you’ll find plenty of elbow room at popular attractions and get to rub elbows with the locals during their most congenial time of year. This itinerary offers a perfect combination of small towns and large, major attractions and new discoveries, all when locals are most relaxed.