Travel Journal

Sailing into History: An Unforgettable Journey on the Sea Cloud in the Southern Caribbean

by Ian Collier

People often say that travel these days can feel pretty generic, making it hard to find something truly special, even in the luxury market. But let me tell you, a week sailing the Southern Caribbean on the four-masted Sea Cloud is anything but ordinary!

Unlike many cruises, with just a maximum of of 64 guests, Sea Cloud has become a destination in itself. This ship has an incredible history, especially in Germany, where it’s known for its colourful past.

Built in Kiel in 1931, Sea Cloud was once the largest private yacht in the world. It was commissioned by Marjorie Merriweather Post, an American cereal heiress, and her husband, Edward Hutton. Post later went on to build the famous Mar-a-Lago in Florida!

There are stories of her design being changed at the last minute to make her the most impressive yacht among the elite. Post even sketched out the ship’s layout in a New York warehouse so she could decide on the furniture for her eight original staterooms. That furniture was then shipped to Germany before the ship made its way back to New York.

Throughout her life, Sea Cloud has seen it all—from surviving four divorces of her owner to serving as a US diplomatic ship before WWII. She hosted important meetings in St. Petersburg and even acted as a navy vessel during the war. After a stint with the Dominican Republic’s dictator Trujillo, she was left to rust until being rescued in the late 1970s and restored in Kiel.

Today, the ship has added more cabins, keeping much of its original charm. Refitted to meet modern standards, it still feels like a step back in time, with beautiful teak and mahogany throughout. The crew works tirelessly to keep everything in top shape, from the woodwork to the brass.

The original staterooms designed by Post remain the most sought after, now featuring air conditioning and modern plumbing. My cabin was delightful, with a marble fireplace and a walk-in closet. There are no keys for any of the cabins, adding to the ship’s relaxed atmosphere.

Sailing on the Sea Cloud is unlike any other cruise. It’s a private yacht at heart, and it feels that way. Even her sister ship, Sea Cloud II, while larger and more modern, has a different vibe.

Dining on board is a highlight, with excellent food served in the original dining room. Breakfasts and lunches are buffets, while dinner is a formal affair with fine wines. The lobster was particularly delicious, and dining felt like stepping back into the glamorous days of the 1930s. The crew runs the operation smoothly, from mealtimes to entertainment, which mainly consists of local history talks and cocktails in the lounge. The dress code is casual during the day and smart casual at night, with opportunities for a fancier outfit on special occasions.

We began our journey in Bridgetown, Barbados, an island often called more British than Britain itself. The ship lectures covered the complex history of European colonization and the sugar trade, which heavily shaped the Caribbean’s past. Our itinerary also took us to Tobago, Grenada, the Grenadines, and St Lucia, all now heavily reliant on tourism.

With fewer guests, Sea Cloud can visit smaller, charming spots like Bequia and Soufrière, far from the larger crowds. If you’re looking for an unforgettable rum punch, check out the tiny ‘Suck Hole’ bar in Tobago—what a treat! We didn’t see another cruise ship all week, making every shore excursion feel exclusive.

A four-masted ship with 30 sails is quite the sight under full sail. Many guests have this experience on their bucket list, and it’s easy to see why—she draws admiration wherever she goes!

Some highlights included a catamaran tour through Tobago Cays, where we snorkelled with turtles and lounged on pristine beaches, feeling like we’d stepped into a movie. Later, we enjoyed a beach barbecue on Union Island, with the crew surprising us with a fantastic feast.

Watching the crew unfurl the sails by hand was a real treat. They climbed high into the rigging to make it happen! Later, we even had the chance to photograph Sea Cloud from one of the zodiacs. With such a spacious deck, there were plenty of quiet spots for sunsets and stargazing. It truly felt like a friendly pirate ship!

By the end of the week, I was fully immersed in the laid-back Caribbean vibe. Each afternoon, I returned to the ship at my own pace, greeted with warm towels and smiles from the crew.

As a vintage vessel, Sea Cloud sails the Caribbean from December to April and the Mediterranean from May to November, with some special transatlantic voyages. I found it interesting that most guests in the Caribbean are German, while the Mediterranean attracts more Americans.

As one of the first New Zealand guests, I felt warmly welcomed. My time on Sea Cloud was everything I hoped for and more—definitely one of the most unique travel experiences around!

 

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