Sailing like a pirate

Updated: Jan 18, 2020

From first glance, the sailboat we booked passage on for a six-night trip from St. Lucia through the Eastern Caribbean reminded us of a pirate ship. Sail Windjammer’s S/V Mandalay was built in 1923 by financier E.F. Hutton for his then-wife Marjorie Merriweather Post of the cereal dynasty. But don’t be misled by the ship’s glamorous past - you won’t be served gourmet food on silver trays by attentive butlers in tuxedos . You’ll be lining up at five o’clock along with your fellow passengers for free rum punch served in plastic cups. The happy hour hors d’oeuvres ranged from very delicious deviled eggs and mini pizzas to cold French fries and soggy fried fish another day. If you’re looking for gourmet food and white-glove service, this is not the cruise for you. If camaraderie and the adventure of exploring rarely visited islands in the Caribbean is what you seek, you can have a great time. The service is lackadaisical at best, but the 33 other passengers on board this week didn’t seem to mind at all. It also helps if you booked with a Groupon two-fer or other special as many passengers seem to have done. We booked full price and were honestly expecting a higher class of service. So, look for a bargain and if you get one, you will love the trip.

The Mandalay is a three-masted 240-foot tall ship.

Captain "Sly" guided the ship and exhibited a fun pirate persona at times.

In keeping with the "pirate ship" impression that we had of the Mandalay, some of the crew members were at times gruff and the accommodations were adequate but far from luxurious.

Our cabin was minimal in luxuries.

Aside from having wonderful fellow travelers, we also loved the off the beaten path stops that the small sailing ship was able to make. The sailing schedule varies according to weather and winds, but ours seems to have been a pretty standard trip. We set sail from St. Lucia on a Sunday night and spent most of the next day anchored at Bequia Island where passengers picked from taking a paid excursion around the island or relaxing at the town beach. The excursion included stops at a turtle sanctuary, a scenic lookout, a local beer bar and a shop of model boat builders.

Bequia is a secluded island in the Grenadines.


The Old Hegg Turtle Sanctuary was founded in 1995 to assist conservation of the endangered hawksbill turtle. Hatchlings are protected until age 5 when they are released back to the sea.

Sargeant's Model Boat Shop was opened in 1966. Today, the Sargeant family continues to use simple hand tools to craft highly detailed miniatures of the sailing ships that used to be built on the island.

We headed to Union Island next where the excursion choices included paid snorkeling or scuba diving. At the small island of Mayreau, we chose the evening "cultural" walk, which was in fact a very entertaining bar crawl. One of our fellow passengers is a bongo player and it was particularly entertaining to see him jam with a local group of percussionists at a hidden-away bar we reached by climbing a long, dark road.

At the Tobago Cays Marine Park on Day 3, we enjoyed a cookout on the beach and really spectacular snorkeling with sea turtles and rays right off the beach. Our guide mentioned that one of the Pirates of the Caribbean movies was filmed nearby, and it was easy to picture Johnny Depp on our beach.

The beach on the Tobago Cays was completely deserted in parts.

Snorkeling with brightly-colored fish and sea turtles is easy to do in the Tobago Cays.

Day 4 was spent at the Tamarind Hotel's beach on the remote island of Canouan, which is now a jet set favorite. Jerry Seinfeld was spotted at the island's only other hotel earlier in the month. For just a $10 fee, we were able to paddleboard, kayak and relax on beach chairs while checking our emails at one of the rare WiFi locations.

Our last day in the Grenadines was spent anchored in Rodney Bay back in St. Lucia. We were able to visit the national park on Pigeon Island via a short trip on the ship's motor launch.

The ship's motor launch took us right to Pigeon Island.