St. Thomas, Sophisticated

A former cruise director revisits the tiny, charming paradise he adored...only to find even more to love.

- STEVE LELAND

St.Thomas had a deep-rooted seafaring heritage long before I plied its waters.

As a cruise director for many years, I visited the small, quaint island every Tuesday. Twenty-five years later, it has matured into destination adulthood, but in spite of its modernization, the island retains its playful appeal. Its protected harbor, once a haven for swashbucklers and trading ships from around the world, is now a playground for chic globetrotters and private yachts. With the ideal attributes of paradise, it’s no wonder that it enjoys the distinction of being the reigning Best Caribbean Cruise Destination from Porthole Cruise’s Readers’ Choice Awards.

In the mid-1700s, the island became a Danish crown colony and evolved as an essential trading destination for vessels from around the world. With the enormous influx of ships loaded with supplies, it was only fitting that the island became such an attraction for pirates.