Small Sailing Ship Cruises In The Caribbean: Expert Review

Small Sailing Ship Cruises in the Caribbean

By Judi Cuervo & Heidi Sarna

It was probably about 40 years ago when I saw my very first sailing ship. I was leaning lazily against the rail of the cruise ship I was sailing in the Caribbean, probably a Carnival or Home Lines ship, when suddenly in the distance appeared an ornate vessel topped with a riot of billowing sails.

“Is that a tourist boat?” I asked a nearby crew member. “All the way out here??” He explained that it wasn’t — it was a private yacht called Sea Cloud.

The Sea Cloud today, captured in the Ionian Sea in July of 2024. * Photo: Peter Knego

Well, that crewmember was partially right. Sea Cloud entered service in 1931 as a private yacht, the private yacht of socialite Marjorie Merriweather Post, no less, but after serving nearly 50 years in a number of incarnations, in 1979, SeaCloud was reborn as a 64-passenger cruise ship. And she’s still sailing today at over 90 years of age.

It might have taken me decades, and the birth of the internet, to learn more about Sea Cloud, but I still trace my fascination with sailing ships — and small ships, in general — to that chance encounter with Sea Cloud sailing in the Caribbean islands

Years later, I sailed a Sea Cloud ship and others of its kind and discovered that navigating the Caribbean aboard a sailing ship couldn’t be further from the experience found on a traditional cruise.

It’s a decidedly laid back affair where the stars, the wind, the glittering turquoise water and those billowing sails provide the bulk of the entertainment.

You are not in a glitzy floating resort, but aboard a vessel that immerses you in nature and plunges you into another time, a time before shipboard production shows, casinos, top-deck waterparks and specialty restaurants.

Aboard small sailing ship cruises, you can leave the stilettos at home and plan to dine on deck under the stars, choosing from a menu of superb dishes filled with fresh, locally sourced ingredients.

A sailing ship doesn’t only offer a different kind of cruise, but a different Caribbean as well — one that features magnificent and uncrowded destinations that large ships couldn’t dream of visiting.

If, like me, you’ve been in St. Thomas on a day when nine (yes, NINE!) mega ships called, you’ll no doubt appreciate the glory of sailing into ports like Jost van Dyke, rich with history as well as home to Foxy’s, the best-known bar in the Caribbean, or crawling through crystal waters around the maze of boulders and caverns that lead to the secret rock pools of The Baths in Virgin Gorda.

Small ship cruise lines including the four we feature in this story — Sea Cloud, Star Clippers, Windstar and Island Windjammers — definitely know the best place to sail in the Caribbean.

You’ll likely board your sailing ship from a bustling island like Barbados, St. Maarten or Puerto Rico but, in no time, you’ll be surrounded by the pristine beauty of places like the resilient Montserrat, resurrected after the 1985 volcanic eruption devastated the island, the remote Bequia and her white sand beaches, Iles des Saintes and her unspoiled beauty and French chic, and the ever-so chi-chi St. Barts.

People from all over the world flock to the Caribbean seeking sun, sand and gentle breezes…and they usually find them year-round.

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Best Time for Small Sailing Ship Cruises in the Caribbean

Consider late January through April or May as a great time to sail in the Caribbean, when it tends to be dry and sunny, a great contrast to the cool or cold weather you may be wanting to avoid if you live in many parts of North America and Europe.

Those particularly concerned about weather conditions might want to avoid sailing in the Caribbean during August through October, considered peak hurricane season.

Another lesser-known Caribbean weather phenomenon you might wish to avoid is the Christmas Winds, trade winds centered in The Windward Islands (Martinique, St. Lucia, St. Vincent, Grenada and the Grenadines). They blow strongest in December and January — these Christmas Winds, which can blow 30-40 knots and build waves up to 10 feet, can make for a pretty rocky ride aboard a sailing ship!

In general, it’s good to have your sea legs when choosing a sailing ship in the Caribbean. For many folks, the whole point is to feel the ship move through the water, spending lots of time up on deck enjoying the ride — up and down and to and fro, with the wind in your hair and the sails flapping and fluttering overhead.

Here are details about four small-ship cruise lines with sailing ships based in the Caribbean during the winter and in some cases, year-round.

We have written about all of these lines extensively, and recommend all four.

4 Sailing Ship Cruise Lines to Consider for Caribbean Vacations

1. Sea Cloud Cruises

Anne Kalosh sailed the 136-passenger, three-masted, all-inclusive (drinks, tips, port charges) SeaCloud Spirit and reports that this historically German line has set its sites across the Pond and hopes that, by year’s end, 40% of its guests will hail from North America.

Meanwhile, QuirkyCruise Contributor Peter Knego has sailed on both the 1931-built Sea Cloud and the Sea Cloud II.

Unlike other sailing ships with mechanically-operated sails, Sea Cloud, SeaCloud II and SeaCloud Spirit are true sailing ships, with their sails set by hand. There’s nothing like watching the ship’s crew members scurry up the masts to manually unfurl these massive sales, creeping slowly — and carefully — across each yardarm.

An unfortunate truth about sailing ships is that the most breathtaking vision of them is viewed not on board, but at sea. And Sea Cloud (and Star Clippers too) has found a way to bring its guests that vision. On each sailing, Sea Cloud ships operate a “photo safari,” with guests taken via Zodiac for a sail around the ship when its sails are fully unfurled — it’s the ultimate photo op!

Beginning in January 2025, SeaCloud Spirit home ports in San Juan, Puerto Rico for the very first time and will celebrate the cuisine of that island on board through culinary programs that feature some of the island’s most popular chefs.

Sea Cloud Spirit under full sail. * Photo: Peter Knego

In her review of the Sea Cloud Spirit, Anne Kalosh writes:

“On the gorgeous tall ship Sea Cloud Spirit, I found the Caribbean of my dreams. Under 44,132 square feet/4,100 square meters of billowing sails, I discovered gems of the Lesser Antilles in all their glory.

At each harbor we visited, our three-masted, square-rigged windjammer was the biggest and most beautiful yacht, drawing admiring looks from everyone.

It was a sophisticated yet casual experience on a luxuriously quirky ship.

On the Sea Cloud Spirit, the focus is on the great outdoors, the wind, weather and stars, and the mechanics of the ship — the sails, the masts, the rigging. It’s quiet and vibration-free without the engines. You feel the motion and the heel of the vessel.

It’s fascinating and a little scary to watch the sailors climb high in the rigging, and simply awesome when the sails unfurl and catch the wind. Meanwhile, crew on deck are hauling the lines with winches as they trim the sails.

You watch them tie the hitches to secure the lines and the meticulous way they coil the lines so they’re tidy and ready to use again. Some of the ropes are arranged like artwork.

You don’t have to know anything about sailing, but you can learn from watching. And on Sea Cloud Spirit, the captain explained the basics in his opening briefing and the chief officer stood on deck with a microphone, narrating the first hoisting of the sails.

There is nothing like the moment the sails take over — it’s both a hush and a rush of wind that’s exhilarating.

Sea Cloud Spirit uses a mix of engine and sail power, with the line aspiring to offer about two full days under sail per cruise.

On my trip, we had two sea days, both under sail, and portions of many more. An announcement was made when the sails were coming up or going down to alert anyone who wanted to watch…”

READ Anne’s full Sea Cloud Spirit review here.

Peter Knego recently reviewed the Sea Cloud, though he sailed in the Med not in the Caribbean; still you get a good feeling for what it’s like to sail on the legendary Sea Cloud. Peter writes:

“Sea Cloud is pure glory afloat, a time capsule of past elegance that continues to provide her guests with joy and awe, well into her 93rd year.

As rich in history as she is in original detail, Sea Cloud was built in Germany in 1931 for American cereal heiress Marjorie Merriweather Post and her financier husband E.F. Hutton as the Hussar V…”

READ Peter’s full Sea Cloud review here.

The Main Differences Between Sea Cloud, Star Clippers and Windstar Cruises

By Anne Kalosh

I’ve cruised on both Star Clippers and Windstar Cruises’ sailing vessels and loved them. Each is different, and Sea Cloud Cruises adds yet another dimension to sail-cruising. I loved it, too.

Like Star Clippers, the Sea Cloud fleet is hand-sailed, but Sea Cloud Spirit is posher, with its glamorously appointed staterooms, gold-plated sinks, gourmet menus and higher price — a luxury experience.

On Star Clippers, passengers get a chance to haul ropes, scramble up the mast for a view from the crow’s nest and soar over the sea in the bow sprit net.

On Sea Cloud cruises, the sailing is left to the crew.

Windstar’s sails are computer-controlled and the vibe is more “cruise-like.” You don’t have to be into sailing to enjoy it.

On Sea Cloud, the sailing is the main attraction and most experiences, including the dining, captain’s welcome and farewell parties, and nightlife, take place outdoors on the Lido Deck.

2. Star Clippers

Imagine scurrying up the mast of Royal Clipper, a five-masted, fully-rigged tall ship, for a bird’s eye view from the crow’s nest or relaxing in the ship’s widow’s nest, gingerly straddling the bowsprit boom before climbing into the spongy net and splaying out in the warm sun for a spell.

Those are just a couple of the nautical things you can do aboard this 227-passenger sailing ship that dazzled even a first-time cruiser during a sailing to Iles des Saintes, St. Lucia, Dominica, Bequia and the Grenadines.

Royal Clipper. * Photo: Heidi Sarna

Heidi has sailed with Star Clippers many times all over the world (including Thailand and the Greek Isles), and one of her memorable Caribbean sailings was aboard the Royal Clipper, with a friend cruising for the very first time.

Plenty of fun from Royal Clipper’s water sports platform. * Photo: Star Clippers

In her Royal Clipper Caribbean review, Heidi writes:

“…This wasn’t any typical cruise.

Our journey began in Barbados, the wintertime base for the 227-passenger, 439-foot-long Royal Clipper, a five-masted, fully-rigged tall ship modeled after the great German clipper Preussen of 1902. The Royal Clipper is a casual, comfortable ship with a seriously adventurous attitude as it island hops across the Caribbean to off-beat, less touristy islands like Les Saintes, Bequia, Dominica, St. Lucia, and the Grenadines.

On such a cozy ship, we easily made lots of new friends from all walks of life. We hiked up to Fort Napoleon on Les Saintes with an endearing Chicago couple, a wise-cracking salesman and his doting young wife, and shared a meal with a charming, French Ben Kingsley lookalike and his glamorous wife, who had sailed with Star Clippers many times before.

We raised our glasses with a group of fun-loving Austrians at the bar and gossiped with a young couple from New Jersey on their honeymoon.

As with all small ships, the atmosphere on the Royal Clipper is intimate and sociable, and everyone gets chummy fast. That’s what makes a journey on this ship so wonderfully different than on a 2,000-passenger mega, where you’re just another face in the crowd…”

Read Heidi’s full Royal Clipper cruise review HERE.

Royal Clipper Cruise to Corsica, Elba & Sardinia

The 227-passenger Royal Clipper. * Photo: Star Clippers

3. Windstar Cruises

Quirkycruise.com reader Don from Toronto reports on his seven-night Caribbean sailing aboard the 342-passenger Windsurf, the flagship of Windstar Cruises.

Unlike Star Clippers and Sea Cloud Cruises, Windstar’s sailing ships have fully electronic sails; there are no sailors climbing the masts! Still, the vibe is alive and Windstar’s sailing yachts put the canvas up whenever the wind (and schedule) is cooperating.

During Don’s cruise, which sailed round trip from St. Maarten, Wind Surf called at St. Barts, Antigua, Jost van Dyke, Totola and Virgin Gorda — islands Don admits he would never have thought of visiting.

By the way, QuirkyCruise’s Heidi Sarna will be cruising on the Wind Surf in Jan (2025) with her husband and adult sons; stayed tuned for her review and social media postings!

Windstar one week sale on Caribbean cruises

The lovely Windward islands of the Caribbean. * Photo: Windstar

QuirkyCruise reader Don also writes:

“The sails are a major feature of the Wind Surf and her fleet mates, and are used as much as possible as long as the weather permits and the destinations can be reached in time. I’ve taken more than 10 cruises with Windstar and consider the service to be excellent with a high passenger/crew ratio.

The food is of a very high standard, and passengers have a number of dining options including AmphorA, the ship’s main dining room, Stella Bistro (French cuisine), Candles (situated on the deck — steak, skewers, etc.), The Veranda (breakfast and lunch on the upper deck), and room service…”

READ Don’s full review HERE.

The 342-pax Wind Surf. * Photo: Windstar

Beautiful Tahaa in the Society Islands. * Photo: Windstar

4. Island Windjammers

Elysa Leonard, another first-time cruiser, sailed to many of those same ports visited by Star Clippers aboard Island Windjammer’s 26-passenger Vela a sailing ship that previously served as a medical-support vessel in the Marshall Islands and then part of the Catalina Island Marina Institute, offering educational course for school age kids.

A passionate scuba diver, Elysa, traveling solo, was seeking tropical fish — and she found plenty, along with terrific camaraderie and sublime dining aboard this quirky 156-foot schooner that welcomes solo travelers year-round with Cadet solo cabins and standard cabins available at a single-occupancy rate.

The Vela and the dinghy launch. * Photo: Island Windjammers

Elysa writes:

“If you want to know what an Island Windjammers Caribbean adventure cruise is all about, think adult summer camp, contagious laughter and completely checking out for a week. I entered the special Island Windjammer world recently when I sailed on a 6-night cruise aboard the 26-passenger Vela round-trip from Marigot Bay, St. Lucia.

Along the way, we visited the islands of Dominica, Iles des Saintes, Marie Galante and Martinique. It was the next best thing to chartering your own private sailing ship; and a heck of a lot cheaper.

The meeting point for embarking passengers was the Hurricane Hole restaurant and bar in Marigot Bay, a short water taxi ride from the hotel where I stayed for three nights before the cruise. Like that first day of summer camp, I felt a bit nervous. Would I be the only single or would there be other solo passengers? Would I like them? Would they like me? My mind was racing with questions.

I met everyone immediately and it was so comfortable. The crew said it happens every week. No matter their differences, passengers seem to magically come together, and for the most part, the differences fade away fast as the shared experience of sailing together on a quirky schooner in the Caribbean takes hold. The ups and downs, literally bring people together — the crew as well as the passengers…”

READ Elysa’s full review here: Island Windjammers Caribbean Adventure (Part 1 ). And here’s Part 2: A First-Time Cruiser Falls In Love With Island Windjammers’ Caribbean Adventure.

A Painkiller Indeed!

Jost van Dyke’s Foxy’s might be the most popular bar in the Caribbean but just down the road from it on the stunning White Bay you’ll find the Soggy Dollar. Legend has it that the bar got its name from its patrons, most of whom swam to shore from their boats or yachts clutching waterlogged dollar bills to spend on rum cocktails at this open-air little beach bar.

Soggy Dollar is where the popular Painkiller cocktail was born, credit for the recipe going to Daphne Henderson, an English bartender who, in 1970, visited Jost van Dyke, the smallest (three square miles) of the four main British Virgin Islands, and never left. Instead, with sand between her toes, she became the bar’s proprietor and created what is undoubtedly one of the most famous cocktails in the Caribbean…cheers!

Painkiller Ingredients:

1 oz. orange juice
1 oz. coconut cream
4 oz. pineapple juice
2 oz dark blended rum, preferably high proof
Grated nutmeg

Directions:

Mix all liquid ingredients in a shaker over ice.
Shake vigorously and strain into a cup of crushed ice.
Top with an additional rum float if desired and garnish with a generous sprinkling of freshly-grated nutmeg.

The Basics of Sailing Ship Lines Cruising in the Caribbean

Seasons:

The Caribbean is a year-round destination, although August through October are considered peak hurricane season.

When sailing the Windward Islands, you might also wish to avoid December and January, as the Christmas Winds can make for a pretty rocky ride aboard a sailing ship!

Cruise Length:

Most sailing cruises in the Caribbean are 6 to 14 days, with week-long sailings being the majority of offerings.

Start/End Points:

Generally, Windstar, Sea Cloud and Star Clippers sail out of the larger islands that have more flight connections — think St. Maarten, Barbados and Puerto Rico.

For instance, Windstar’s Wind Spirit typically sails round trip from Barbados, while the Wind Surf often sails out of St. Maarten. Meanwhile, SeaCloud Spirit sails round trip from San Juan, Puerto Rico beginning in January 2025.

Island Windjammer’s Vela sails from a variety of Caribbean ports, including Grenada, St. Lucia, St. Maarten, Dominica, Tortola, Turks & Caicos or St. Kitts, depending on the cruise.

Interested in One of These Small Sailing Ship Cruises in the Caribbean?

It’s hard to go wrong when choosing one of these sailing ship lines cruising the Caribbean for your next vacation. They all promise a casual, classic fun-in-sun cruise under sail, along with comfy amenities too.

To learn more about quirky sailing cruises in the Caribbean, drop us a line if you need help booking — Heidi@QuirkyCruise.com — or directly contact Star Clippers, Sea Cloud Cruises, Windstar Cruises or Island Windjammers.