With a flute of Pommery Champagne in hand, I imagined myself as legendary American heiress Marjorie Merriweather Post while the crew of riggers secured the 23 sails for the night.
The aft-deck breeze ruffled my hair and my skirt swirled around my ankles as I gently slurped an oyster from its shell. The orange sun slipped into the gentle sea behind some 380 feet of teak deck stretching from bow to stern on my yacht.
Well, make that Sea Cloud Cruises’ yacht — the deck of sailing yacht Sea Cloud II, to be precise, on which I and 90 other passengers were gliding through the Caribbean in grand style. Sea Cloud, the line’s first vessel, was originally designed and decorated by Post (a businesswoman and heiress to the General Foods group) and her husband, financier E.F. Hutton, in 1931. Though the yacht has undergone restorations and updates over the decades, much of its original character remains intact today.
A Well-Seasoned History
“Heritage and authenticity — that’s what sets Sea Cloud Cruises apart,” said Bill Smith, legendary travel executive and fellow traveler on my sailing. With prior careers at Silversea, Crystal Cruises and Virtuoso, to name a few, Smith came out of retirement last year to act as brand ambassador for Sea Cloud Cruises.
His reasons are personal. Sure, his son, Kevin Smith, is the line’s vice president of sales. But what really hooked Bill, who has lived onboard his own 55-foot sailboat for many years, is that Sea Cloud Cruises' three ships are actually powered the old-fashioned way — by the wind.
This is nothing to scoff at. My husband, another old salt, groused nonstop the one time we cruised onboard a ship with mechanically controlled sails. Sea Cloud Cruises met his approval, along with that of other sailing enthusiasts on this voyage.
An ‘Old Money' Aesthetic
For non-sailors like me, Sea Cloud II exudes the casual elegance of “old money.” While Post’s original yacht is getting a makeover, sister ships Sea Cloud II and Sea Cloud Spirit are channeling its aura.
Rich wood paneling and nautical accents create a timeless atmopshere onboard.
Credit: 2026 Carolina BejaranoCorridor and stateroom walls are trimmed with burled mahogany above an ocean of marine-blue carpet. Bathrooms are marble and offer plenty of storage. Brass fittings — on railings, lamps, latches and just about everywhere else — are polished so frequently that smudges dare not linger. Little appears to have changed since Sea Cloud II first launched in 2001, and that’s a good thing.
Lloyd Schafer, a passenger from Lancaster, Pennsylvania, was impressed with the ship’s spotless appearance.
“I don’t know how they keep the cabins so perfectly,” he said. “There isn’t even a mark on the carpet from where the chairs have been moved. It’s really better than any hotel I’ve ever stayed in.”
My Category E Deluxe Stateroom, one of the ship’s smaller cabins, measured 204 square feet. It was spacious enough for a California king bed, two sitting chairs, a coffee table, a desk, an armoire (all in polished wood) and a wardrobe big enough for two. Sunlight beamed through a pair of portholes; upgraded staterooms have larger, curved windows. There are no balconies.
An Intimate Social Experience
Despite the refined decor, the onboard vibe is breezy. Lunches and most dinners are served on the covered aft deck, from casual buffets of fresh salads and hot proteins such as ribs, duck and fish to vegetables grilled outside. Entertainment comes from a versatile keyboard player who whips out rock-and-roll favorites, a classical opus and sea shanties for a crew sing-along. Attire is similar to any Caribbean cruise: T-shirts and sandals by day, sundresses or trousers for evening. Even at the welcome and farewell dinners served in the formal dining room, few men wore jackets.
“This experience is for someone who doesn’t want a big ship,” said Uf Tukel, who recently launched his third travel startup, CruiseClub.com. “It’s an intimate social experience — authentic and upscale.”
On any cruise, what matters most is how one spends their time. Like sailing itself, the pace onboard Sea Cloud II was leisurely, both on and off the ship.
Shore excursions feature experiences such as private rum tastings in Caribbean ports.
Credit: 2026 Carolina BejaranoA few excursions were offered in each port, such as kayak tours, historic walks and private rum tastings, where I learned what separates clear and dark spirits (time in barrel). Like many other guests, I often wandered on my own, savoring villages too small for most of today’s large cruise ships.
“If you want a relaxing week, this is the way to go,” said Trish Readybaugh of Rhode Island, who was on her second Sea Cloud II cruise with a trio of couples.
That ease plays into a growing trend in luxury travel.
With itineraries ranging from week-long Caribbean cruises to Mediterranean voyages and transatlantic crossings, Sea Cloud II offers repeat guests plenty of opportunities to experience different regions.
“A lot of people are looking to slow down,” said Beth Butzlaff, general manager, U.S. for Virtuoso. “There’s an evolution of luxury; it’s all about authenticity and richness. People want to be part of the experience.”
On Sea Cloud II, that means watching the daily hoisting and dropping of the sails and learning how those sails power the ship. When seas are calm enough, the heartiest passengers can climb the rigging — carefully harnessed, of course.
Adventurous guests can climb Sea Cloud II's rigging for a sailor's-eye view.
Credit: 2026 Carolina Bejarano
But the winds and currents don’t always cooperate. As Butzlaff points out, this is not a setting for people with mobility issues. (Those clients will fare better onboard Sea Cloud Spirit, which features an elevator.)
During my voyage, conditions were too choppy to lower the ship’s marina sports deck. The elements interrupted the itinerary; when weather got too rough for boarding the tenders that would take us to our designated port, the captain moved to calmer waters.
Few guests seemed to care — some played games at tables near the covered bar, and interested parties caught history talks by the retired admiral who lectured onboard. Meanwhile, I grabbed a book from the library and curled into a deck chair, indulging in the fantasy of a bygone world.
