There is nothing quite as magical — or romantic — as a cruise on a sailing ship.
To stand on the deck of a vessel topped with dozens of billowing sails, propelled through the waves by the power of the wind alone, is to go back in time to an earlier age of travel, when crossing the world’s oceans was as adventurous as it was challenging.
It’s an experience that’s all about the feeling of the wind in your hair, the lean of the vessel (known as the heel) as it’s pushed by the wind and the sway from the waves (which is actually smoother than what you get on a motor ship).
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In contrast to what you’ll find on so many motor-powered ships, cruising on a masted ship is about the simple thrill of traveling across the sea and not about all the many attractions you’ll find on board.
Only a handful of small cruise brands — so small that you might never have heard of them — offer trips on sailing ships. Here, we look at the three biggest players in this niche subset of the cruise industry.
Sea Cloud Cruises
If it’s an authentic, old-style sailing experience you want, then Sea Cloud Cruises is the line for you. The Germany-based company operates three large sailing ships where the sails are unfurled by hand, just as they were on sailing ships centuries ago.
On the biggest of these three vessels, the 136-passenger Sea Cloud Spirit, 18 deckhands scurry high into the rigging on sea days to manually untie and prepare the sails, an amazing sight. Unveiled in 2021, it’s a full-rigged, three-masted sailing ship of the sort that hasn’t been common on the world’s oceans for more than a century.
Related: Why Sea Cloud Spirit is a sailing vessel you’ll want to try
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Sea Cloud Cruises’ two other vessels — Sea Cloud 2 and Sea Cloud — are smaller but offer a similar show as the sails are set by hand the old-fashioned way. The former is a 23-year-old, three-masted barque propelled by 23 sails (five fewer than Sea Cloud Spirit); the latter is a 93-year-old, four-masted barque with 30 sails and a storied past.
Now configured to carry 64 paying passengers, Sea Cloud was originally the private yacht of Postum Cereals heiress Marjorie Merriweather Post and her husband, the famed financier E. F. Hutton. At the time, the vessel was the largest private yacht in the world. It later served the U.S. Navy as a weather ship during World War II, after which it became the presidential yacht for the Dominican Republic. It only began sailing as a cruise vessel in the 1980s.
If you have money to spare, you can still book Post’s opulent private quarters on Sea Cloud, now its owner’s suite. It’ll set you back around $5,000 per day per couple. Her husband’s slightly smaller quarters are also available to book at a similar rate.
Post, the wealthiest woman in the U.S. during her lifetime, notably also built Mar-a-Lago, the massive estate in Florida that is now the official residence of Donald Trump.
Sea Cloud Cruises is the most all-inclusive and upscale of the three brands listed in this story, with pricing to match. Expect to pay nearly $1,000 per person per day or more for many sailings.
Sea Cloud Cruises’ three vessels offer a diverse array of sailings in the Mediterranean, Northern Europe, the Canary Islands and Morocco, the Caribbean or along the west coast of Central America.
Related: Cruising Costa Rica, Panama with Sea Cloud Cruises
Windstar Cruises
Founded in the 1980s, Windstar Cruises got its start as a sailing ship line. While it now operates traditional motor-powered ships, too, voyages on sailing ships are still a big part of its business.
Three of the Seattle-based brand’s six vessels — Wind Spirit, Wind Star and Wind Surf — are sailing vessels, and they all offer a similar yacht-like, small-ship experience.
Two of the three vessels (Wind Spirit and Wind Star) are particularly intimate, measuring 5,407 tons and carrying just 148 passengers with every berth full.
Related: The 2 types of Windstar ships, explained
The line’s third sailing vessel, Wind Surf, is nearly three times the size at 14,745 tons. It’s one of the biggest sailing ships in the world (only a sister vessel that sails for Club Med is bigger). Wind Surf carries 342 people, an enormous number for a sailing ship.
Unlike on the vessels operated by Sea Cloud, the sails on Windstar’s sailing ships aren’t unfurled by hand in the old-fashioned way but by the push of a button from the bridge. It’s a fully automated system that is much more modern, if less dramatic.
Still, the experience of slicing through the waves by the power of the wind alone on Windstar ships is as glorious and romantic as it is on the Sea Cloud ships.
Windstar Cruises is less all-inclusive and pricey than Sea Cloud but still offers a relatively upscale experience. Its dining program is done in partnership with the food-focused James Beard Foundation, which also brings James Beard Award-winning chefs to the ships regularly for food-themed itineraries.
For an extra $89 per person per day, passengers can also make the experience more all-inclusive with included Wi-Fi, unlimited beer, wine and cocktails, and gratuities (three things that aren’t included in regular fares).
The line’s three vessels typically spend nearly all of their time sailing in the Mediterranean, the Caribbean or along the west coast of Central America.
Related: Read more about Windstar’s itineraries
Star Clippers
Like Sea Cloud and Windstar, Star Clippers operates three sailing vessels that are among the biggest and most elegant sailing vessels in the world.
The belle of the ball at the line is Royal Clipper, a stunning five-masted ship that is billed as the largest square-rigged ship in the world. Its enormous array of 42 sails has a sail area of 56,000 square feet — significantly more than the sails atop any of the Sea Cloud or Windstar vessels. (Only Sea Cloud Spirit comes relatively close with a sail area of 44,100 square feet spread across 28 sails.)
Built to resemble Preussen, a legendary tall ship of the 19th century, the 24-year-old Royal Clipper shares the spotlight at Star Clippers with two smaller sister vessels, Star Flyer and Star Clipper.
Carrying 166 passengers apiece, the smaller vessels were designed to resemble the speedy clipper ships of the 19th century, which were known for their narrow profile and large sail area. Each vessel has a sail area of 36,000 square feet spread across 16 sails, a large amount for the size.
When it comes to the setting of sails, Star Clippers vessels offer a level of old-style authenticity that is in between the ships of Sea Cloud and Windstar. Like on Sea Cloud vessels, the sails are pulled into position by a team of deckhands using hand power and winches to tighten the “sheets,” or ropes.
Unlike on Sea Cloud vessels, the deck hands don’t climb high into the rigging to untie and prepare the sails for winching. That part is done automatically at the push of a button from the bridge, as it is on Windstar vessels.
In one key difference, though, Star Clippers lets passengers harness up and climb into the crow’s nest of its vessels — a thrilling experience. Just be prepared for your knees to go a bit wobbly as you get to the top; it’s way up there.
Star Clippers sailings are the most affordable option among the three sailing brands, in part because the onboard experience is less all-inclusive and upscale.
The three Star Clippers vessels mostly operate sailings in the Mediterranean, the Canary Islands, the Caribbean and along the west coast of Central America.
Bottom line
It’s still possible to get a taste of what traveling the world’s oceans was like in the days before motor power. Three small cruise companies — Sea Cloud Cruises, Windstar Cruises and Star Clippers — offer voyages on large sailing ships that are as majestic as anything that has sailed the seas in centuries past.
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