Historic and romantic, the medieval town of Monemvasia is situated on the island nicknamed the “Gibraltar of the East,” an enormous hunk of rock rising from the sea and creating a natural fortress for its inhabitants. Only a single causeway links Monemvasia with the mainland, and visitors must leave cars behind to explore the walled town carved into the cliffside. Ancient stone houses with terracotta rooftops look out over the crystal blue waters and mountains beyond. There are six museums and many churches, including Agia Sophia, among the oldest Byzantine churches in Greece.

Perhaps no port of call is better designed to welcome a luxury yacht than Monte Carlo, where some of the most splendid vessels in the world make their home. At this playground for the rich and famous, the only thing more spectacular than the yachts filling the harbor are the luxury cars driving the winding streets that host the annual Grand Prix. Verdant mountains ascend abruptly behind the lavish high-rises lining the bay, and perched on the cliff is the Palace of the Prince, where the Changing of the Guard attracts onlookers each morning at 11:55.

Numerous islands and hundreds of tiny cays form the nation of the Bahamas. Small at just 21 miles long and nearly seven miles wide, New Providence Island boasts numerous white sand beaches as well as the vibrant capital of Nassau. In the lively city center, the National Art Gallery and Junkanoo Museum showcase the fine art, unique traditions and colorful crafts of the local culture that melds African, English and West Indian influences.

Norman Island is vintage Caribbean paradise: small, privately owned, uninhabited except for wild goats, and accessible only by boat or helicopter. On Norman’s north shore is the sheltered bay known as the Bight, one of the greatest natural anchorages in the British Virgin Islands. At the bay’s entrance, sea caves are renowned for snorkeling. Just offshore, the rock formations known as the Indians are another premier snorkeling spot.

Gorgeous beaches, aquamarine waters, abundant sunshine and cooling trade winds have long been Aruba’s calling card. This Dutch island captivates with diverse outdoor options – world-class golfing, windsurfing, snorkeling and diving – the distinctly bent divi-divi trees and striking geological formations. The desert-like landscapes and rugged coastline of Arikok National Park are the focus of eco-explorations.