St. Thomas, Sophisticated
Porthole Cruise Magazine|March/April 2021
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.

Swashbuckling and scalawag stories abound, and whether they are accurate or not is irrelevant. What is true is that the rumored booty of Blackbeard and Bluebeard has given way to the bounty of Calvin Klein and Ralph Lauren. The once-crowded sidewalks of Main Street have recently been reimagined into a pedestrian utopia of shops and boutiques that branch off into alleyways like Palm Passage, where old stone warehouses play host to designer stores and sidewalk cafes. The colonial architecture provides a colorful facade to shops offering fashion, china, crystal, perfumes, gold, and diamonds. Not only will shopaholics find added elbow room, but because St. Thomas is part of the U.S. Virgin Islands, they are also treated to a duty-free allowance twice as high as would be found elsewhere in the Caribbean.

Continue reading your story on the app

Continue reading your story in the magazine

MORE STORIES FROM PORTHOLE CRUISE MAGAZINEView All

Sipping on the Sand

The unique beach bars near South Florida’s cruise ports are a perfect reflection of the shorelines they represent.

1 min read
Porthole Cruise Magazine
March/April 2021

St. Thomas, Sophisticated

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

4 mins read
Porthole Cruise Magazine
March/April 2021

Traditional Tlingit Tastes

In Hoonah, Alaska, food is about much more than just what's on the plate.

5 mins read
Porthole Cruise Magazine
March/April 2021

Mardi Gras Déjà Vu?

The ships couldn’t be more different, but the return of the Mardi Gras name to Carnival’s fleet may just bring revolution and renaissance to the line and industry all the same.

6 mins read
Porthole Cruise Magazine
March/April 2021

Preastoric Art

A Rising Star in the Art World

1 min read
Porthole Cruise Magazine
March/April 2021

Let's Get Physical

Having long marveled at the technology of the high-end workout equipment on the high seas, Porthole goes all in on putting together a home fitness center.

3 mins read
Porthole Cruise Magazine
March/April 2021

From Russia With Love

Seen throughout Alaska, the matryoshka nesting dolls are as poignantly meaningful as they are increasingly adorable.

6 mins read
Porthole Cruise Magazine
March/April 2021

CONNOISSEURS OF COZY

Amsterdam has launched a lifestyle based on the convivial concept of gezelligheid: lively, comfortable contentment.

5 mins read
Porthole Cruise Magazine
March/April 2021

25 Celebrating Twenty-Five Years of Cruising

A Milestone, but far from Mission Accomplished...

4 mins read
Porthole Cruise Magazine
March/April 2021

RIDING THE STORM

THE BEST TIME FOR BIRDERS TO SEE THE FASCINATING STORM PETREL IS DURING A STORM. IN FACT, SOME LEGENDS CLAIM THE SEABIRD CAUSED THE STORM.

5 mins read
Porthole Cruise Magazine
November/December 2020