Island Windjammers Reviews

Year Started: 2007
Ships in Fleet: 1
Category: Expedition

Summary: Picked up where Windjammer Barefoot Cruises left off - one small sail ship full of party people and pirates. A loyal following.


Island Windjammers Editor's Review


With tiny galleys, small ships and limited crew, you would think that the food on board would be very basic. Surprisingly, the cuisine is one of Island Windjammers strong suits. Dishes are creative and incorporate fresh ingredients (fruits and vegetables harvested that morning and fish caught that afternoon, for example). What you won’t find is variety; there is only one choice for each meal, although special diets and tastes are easily accommodated.


Breakfast is served in the dining area below deck and always consists of a hot item presented individually. Only breakfast the last morning is a buffet. One morning you might wake to pancakes and sausage, omelets and breakfast potatoes, eggs benedict with lobster or the universally-loved West Indian salted fish served with small fluffy biscuits somewhat akin to a savory donut. Fresh fruit, yogurt, juices, coffee and cereal are always available and if you don’t like the choice that day, the chef is happy to prepare eggs any way you like.


Weather permitting, lunch is served under awnings on deck in a comfortable outdoor dining area with a beautiful varnished table and built-in padded booths. Each entrée is delivered tableside and on our cruise ranged from a cheeseburger with fries and coleslaw to fresh fish with potato salad. Dessert might be a white chocolate macadamia nut cookie with whipped creme or a mango sorbet.


Dinner is also served on deck and there’s nothing more delightful than the view as the sun sets in the Caribbean and a light breeze blows across the deck. There are usually three courses, consisting of soup or salad, an entrée and dessert (although on a few occasions the selections might expand to four courses). The chefs really shine at dinner where the flavors are sophisticated yet relatable. On our trip, the cream of pumpkin soup, Thai vegetable spring rolls with a sweet chili sauce, and fresh wahoo with a coconut cream sauce and polenta were often talked about for days, as was the pork loin with mango chutney. Desserts are excellent but on our cruise once the chef discovered our love for his mousse and creme brulee, he changed the menu to accommodate the tastes of the guests on board.


Because each dish is prepared individually, the chef asks that guests notify him if they plan to dine ashore for lunch or dinner. Though some sample the local fare in the ports of call, by the end of the cruise the chef’s reputation precedes him and almost everyone eats their meals aboard. Once on every cruise, dinner is brought ashore to a beach for a cookout with ribs, chicken, salad, rice and beans.


Though there is no room service. A basket of snacks such as nuts, crackers and cookies are always available in the lounge.  Behind the bar, filtered water is on tap. In a small refrigerator are bottles of wine for guests to help themselves and out on deck are two coolers, one filled with beer and the other with sodas. If you prefer stronger spirits, you’re welcome to purchase the alcohol of your choice ashore and bring it on board. The ship can provide a limited number of mixers. The result of the liberal beverage policy and complimentary beer, wine and soda is that you can spend a week aboard and never have a bar tab.


Each day promptly at 5pm, shipboard happy hour begins in the lounge with complimentary rum punches and an assortment of hors d’ouvres such as conch fritters, coconut shrimp, deviled eggs, crackers with seafood mousse, tortilla chips and fresh guacamole. At least once each cruise, happy hour takes place on the beach.


Accommodations are tight by large cruise ship standards, perfectly adequate for their purpose on these Caribbean sailing trips and commodious in comparison to what one might find on a sailboat. Anyone who sailed with Windjammer Barefoot Cruises will note that the fit and finish of the cabins on Island Windjammers are to a considerably higher standard. Bathroom countertops are granite, most cabins offer a separate toilet and shower (although in some single accommodations the shower and toilet might be in the same compartment), there is a plug for razors and a hair dryer is provided.


Closet space is very limited but since guests are encouraged to pack light, it proves sufficient. There is space under the beds for storage and guests are asked to bring only soft-sided luggage such as a duffel bag. Note that there is no space on the ship for storage of hard-sided luggage so take Island Windjammer’s packing tips seriously.


Cabins do not have phones, iPhone charging stations, Wi-Fi, sound systems or televisions and on such casual cruises as these, none of those amenities from larger ships is missed. A rather sophisticated, individually-controlled air conditioning system pumps out plenty of cool air and is supplemented with a wall mounted fan. Reading lights above the beds and small portholes bring in plenty of light along with the ceiling mounted light.


Bedding is comfortable, although Island Windjammers has wisely chosen to steer clear of the big ship battle for bedding superlatives with descriptions of feather-light duvets and pillow menus. On Island Windjammers' ships, sheets are clean, blankets fluffy and pillows plump. With the motion of the ocean and a full stomach after a lovely evening meal, sleep comes easily.


The beds themselves vary from narrow bunkbeds to wider beds comparable to a double or even queen size mattress. The specific arrangement of the beds and their size is entirely dependent on the cabin layout and although they can be somewhat small, guests do not complain and consider the close quarters part of the charm. Beds are made mid-morning at the same time bathrooms are cleaned and supplies replenished. Interestingly, showers in some cabins are bigger than those found on contemporary mass market cruise ships. Be aware that there are no bathtubs on either ship.


Since both Diamant and Sagitta are very small vessels, cabin dimensions conform to the shape of the hull based on their location within the ship. Though some cabins might be similar, each is unique and varies in size. Single cabins are little more than a bed with space to turn around but still comfortable for solo travelers. To give you some idea of the space in the cabins, note that Diamant has three cabin categories: Cozy, Standard and Deluxe. Sagitta also has three: Solo, Standard and Owner’s. Only Sagitta has cabins specifically for single travelers. Single travelers on Diamant pay a surcharge for single occupancy. Island Windjammers does offer a share program where they will pair you with another single traveler.


 Note that there are no cabin keys because they’re simply not necessary on such a small vessel where everyone knows everyone else. You can lock you cabin from inside and if you insist on having a key to lock your cabin when you leave, it can be provided if you ask, although no one really does.

Fellow Passengers

Almost all of Island Windjammers guests hail from the United States or Canada and generally range in age from 40 to 65 with most guests in their mid-50s. During the summer months, children might be aboard. For a cruise that is essentially a sun and sand tour of the Caribbean, Island Windjammer’s guests are well-educated and extremely well-traveled. Dinner conversations often lean toward discussion of hiking in Nepal, an African safari, a trip across the Australia, the temples of Thailand or a prior cruise on the Amazon or the Nile. No matter what a traveler’s background, guests are exceedingly friendly. Social status disappears the moment guests step on the gangway and the CEO of a paper company and a schoolteacher are just as likely to become friends as a group of retirees or two honeymoon couples.


With only 12 to 24 guests on board, it would be easy to be concerned that you could be stuck for a week or more with people that you might not enjoy. The wonderful part of a niche product like Island Windjammers is that it is a very unique vacation that is not for everyone. And for that very reason, guests onboard have much in common simply by having chosen the Diamant or Sagitta. With small sailing vessels and close quarters, everyone respects personal space and there’s no problem finding a spot at the railing to be alone with your thoughts.


A considerable number of guests have sailed on Windjammer Barefoot Cruises and t-shirts and beach towels from the defunct company are often visible in abundance. With a love of casual Caribbean sailing, guests regale each other with stories from their prior adventures and staff from the past yet this passion doesn’t exclude the rest of the guests from feeling they are part of the experience even if they’ve never set foot on a sailing vessel, let alone the much-loved ships of Windjammer Barefoot Cruises. Even those with a fondness for “the old days” quickly come to appreciate that Island Windjammers honors the memory of ships long gone but has created something fresh and new.

Shore Excursions

If you’re used to the pricier shore excursions of larger cruise lines, you’re in for a pleasant surprise with Island Windjammers. With larger lines, mark-ups of 50% to 100% are not uncommon but Island Windjammers views shore excursions as part of the overall experience and not a profit center. While an all-day hike up Gros Piton on St. Lucia might run as much as $145, that is one of the most expensive shore excursions offered. Most three-hour island tours are in the $20 range and even horseback riding through a rainforest checks in at only $40. A day at a resort hotel’s pool can be had for just $15.


With Island Windjammers, shore excursions are assembled from a bag of possibilities based on the interests of the guests on board that particular cruise. The captain or operations manager works with only a handful of tour companies. In most cases, tours for guests are simply assembled by onboard staff using taxi drivers, store owners and hotel proprietors they know by name and have worked with for years. If a contingent of guests is interested in scuba diving, the staff can arrange it even if it’s not offered as an actual chore excursion. If there’s an interesting batik factory or rum distillery, that can become a tour of its own and the amount of time spent there is often the result of a democratic vote among guests. Almost all ports of call have some form of island tour as a shore excursion offering and guests often use the tours to get their bearings to decide what area of the island to explore later in the day. In about half the ports, a choice of two shore excursions might be offered.

Past Passenger Programs

Once you sail with Island Windjammers, you automatically become a part of their past guest reward program called Love For Sail and can save an extra $100 on your next sailing. Guests with 2 to 10 cruises under their belts are called Bosuns, those with 11-20 cruises are First Mates and with more than 20 cruises, you qualify at the Captain level. Bosuns can save from $100 to $200 depending on the length of the cruise, First Mates $200 to $400, and Captains $500 regardless of cruise length. As an added perk, past guests earn a free six-night cruise upon completion of the 20th sailing.


The beauty of Island Windjammers is that you are experiencing the Caribbean as if you were on your own private sailing yacht and that means that casual comfort is the order of the day and night. You won’t need any dressy clothes at all. During the day, most passengers wear shorts and t-shirts and are either barefoot while onboard or wearing flip-flops or sandals with straps. If you’ve been swimming off the ship, a bathing suit and cover-up for the day are not at all uncommon. Evening attire varies little, although sometimes t-shirts give way to a short-sleeved polo shirt and ladies might choose a light sundress.  With the ship underway and a sea breeze, it can sometimes be a bit chilly at night and a light jacket or windbreaker is helpful even in mid-summer


Going ashore, you might find a good pair of walking shoes useful since there are plenty of opportunities to explore. The islands have many trails and hiking paths, some of which can be a bit challenging, so if you plan on hiking, bring sturdy shoes that you don’t mind getting wet or muddy. With many days spent on the beach, tasteful bathing suits, hats, aqua shoes or sandals are suggested.


Guests on Island Windjammers are there for the experience and not to show off their style, clothing or jewelry. The focus is always on being comfortable and packing light since cabin storage space and closets on these smaller vessels are at a premium.


Suggested tips range from $100 to $150 per person per week and can be charged to your onboard account at the end of the voyage. Based on the exceptional service, friendliness of the crew and the overall experience, most guests tip at the high end of the company’s recommended range. The tips are then distributed by the captain among the staff after the guests disembark.


What do you do if your favorite cruise line stops operating? If you’re a dedicated group of former Windjammer Barefoot Cruises passengers, you start your own. When Windjammer Barefoot Cruises turned out the lights in 2007 after 60 years of operating restored sailing ships in the Caribbean, there were thousands of disappointed guests with no similar vacation options.


With true can-do spirit, former guests raised the funds to purchase their own ship. Thus, in 2009, Island Windjammers was born and the 12-passenger Diamant began year-round cruises in the Grenadines. One tenth the size (by passenger count) of even the smallest of the former Windjammer Barefoot Cruises vessels, the Diamant was an instant hit. Even as the many past guests of Windjammer Barefoot Cruises clamored to get aboard, a funny thing started to happen: the new Island Windjammers began attracting an entirely new group of travelers as well.


Though the initial idea was to fill a void left by the shutdown of Windjammer Barefoot Cruises, Island Windjammers is not a recreation of the former company. It is an entirely new enterprise that has developed its own loyal following and personality entirely independent of the company that originally inspired it. Most guests who have sailed both point out that Island Windjammers ships are nicer, cabins cleaner, food better, vessels newer and the company far better run than Windjammer Barefoot Cruises.


The company rekindled the soul and spirit of its predecessor and developed its own unique product. With the success of the Diamant, bigger things were in store for Island Windjammers. In 2012 they purchased the 24-passenger Sagitta, a former vessel with the Swedish Navy which had been operating most recently in the Galapagos Islands. For a company that only has room to carry about 1,800 people a year and has been in operation for only four years, it’s a testament to their popularity and success that they have nearly 25,000 followers on their Facebook page. Clearly, they are doing something right.


Generally, the ships stick to the same itineraries most of the year. The Diamant measures just 101 feet in length and carries only 12 guests, offering year-round 6-night cruises from Grenada to a selection of ports chosen from Carriacou, Union Island, Bequia, Tobago Cays and Mayreau. Guests board on Friday and disembark the following Thursday. The Sagitta stretches 120 feet and can carry double the number of guests, 24. Sailing from St. Maarten on 6-night cruises, the Sagitta travels to ports such as Anguilla, St. Kitts, Nevis, St. Barts, St. Eustatius and Saba. Guests board on Sunday and disembark on Saturday.


However, a few times each year the ships wander away from their standard cruising grounds with longer voyages between St. Maarten and St. Lucia, Grenada and St. Lucia and even Grenada and St. Maarten. The company’s website at has the latest sailing schedules.

The Experience

You could say that this is a cruise in name only but even if you did, you wouldn’t be correct since there’s a specific reason the company is called Island Windjammers rather than Island Windjammer Cruises. This is as far removed from a traditional cruise as a hang glider is from a jetliner. And that’s precisely why guests love it. Forget everything you know about a cruise with casinos, shows, multiple bars and lounges, a dozen restaurants, waterslides, organized activities, rigid sailing times and expensive shore excursions, and gift shops. You won’t find any of that on a voyage with Island Windjammers.


Sailing with Island Windjammer is as close as you can come to chartering your own sailing yacht (and they’re happy to arrange ship charters if you ask). Guests are onboard to relax and recharge but they are intellectually curious enough to make their own fun. There are no activities planned other than meal times and happy hour. One night guests might play charades, another night a board game, another night just sit and chat and on yet another night swim alongside the ship at anchor in the glow from underwater lights on the ship’s hull. The closest you come to shipboard pool is the sea next to the ship and the closest to a waterslide is the rope swing dangling from one of the ship’s masts.


On a big cruise ship, you wait in line for the tender or queue to disembark after an early morning arrival in port. On Island Windjammers, you walk down a few steps to the inflatable zodiac, the crew brings down your bags and you’re off for the day. Total elapsed time: less than a minute. If you’re having fun ashore, the captain might change the sailing time that night to allow for more time. If the guests, which range from 12 to 24 in number, would prefer to skip one port and visit another instead, the captain will do so if sea conditions and distances allow. In a world of cookie-cutter scheduling, each Island Windjammer voyage is unique.


There is no gift shop. Instead, the crew will show you a few t-shirts, hats, towels, luggage tags, and cups for sale by setting them on a table in the lounge.


Both the Diamant and Sagitta are small and that is their appeal. The ships visit ports off limits to large ships such as Saba, Bequia, St Barts, Nevis, Tobago Cays or Anguilla. You go ashore with nor more than two dozen shipmates who have become your friends rather than traipse ashore with thousands of strangers from a large cruise ship. There is something uniquely liberating about seeing the Caribbean through the eyes of Island Windjammers.


You are a name and not a number. By the end of the first day, the crew knows you by name and by the end of the second day, you know all your fellow passengers by name as well. Friendships develop quickly, barriers break down and the days are filled with conversation, laughter and story-telling. Modern cruise ships are large resorts; Island Windjammer’s vessels are small bed and breakfasts.


On such small ships, you feel at one with your surroundings. So much time is spent on deck, you’ll never miss a sunset or a moonrise. Gaze into the ocean and you’ll see tropical fish or sea turtles swimming in the clear water. In fact, you won’t ever need to pay for a shore excursion to snorkel. Island Windjammers hands out fins, masks and snorkels to use throughout your voyage. There is no charge and at the end of the cruise you just leave it in your cabin. The captain knows the best spots to snorkel and will take guests to reefs and rock outcroppings on the ship’s zodiac. Many of the beaches are so pristine, that guests bring their gear ashore and snorkel on their own as well.


Ask and a crew member will show you the engine room and when the ship is underway, you’re not only free to stand watch with the captain on the bridge, you can even take your turn at the helm. Contrary to perception, this is not a cruise where you have to work and help raise the sails. The crew is here to serve the guests and the casual atmosphere is all about maximizing the enjoyment of every paying passenger.


The only drawback to the small sailing ship lifestyle is that there are only a handful of public spaces. But this is rarely a problem since there’s also plenty of deck space if you want to stretch out. Be aware that due to their small size, the Diamant and the Sagitta feel the motion of the ocean. You will always feel movement on board, even when at anchor. For the most part, it is relaxing and will rock you to sleep even in the middle of the day. If you choose this type of vacation, you’re probably not particularly prone to motion sickness. If the seas get a bit choppy, you can really feel movement but in most cases, a healthy dose of Dramamine is sufficient. The ship generally never spends more than six or seven hours sailing at a single stretch so even if you get a bit queasy, it won’t last long.


Overall, Island Windjammers is infused with the laid-back spirit and outdoor lifestyle of the Caribbean islands the ships visit. Each day unfolds without a lot of planning and schedules are modified to suit the whims of the guests whenever possible. On a large cruise ship, you are part of a well-oiled experience that is repeated each week with every detail carefully considered. On Island Windjammers, every cruise is unique, casual beach comfort is the dress code and friendships are made easily.

Kid's Excursions

Kids 7 and under are not allowed on board. There are no formal activities for adults, let alone children, but that doesn’t mean that children 8 and over aren’t welcome. It’s not uncommon for grandparents to travel with grandchildren, especially during the summer holidays, or a multi-generational family to reserve several cabins. The crew loves kids and though there are no children’s programs offered, the captain will show them the bridge, let them steer the ship with supervision and might even take them for a ride in the ship’s zodiacs or go on a snorkeling adventure. With only 12-24 passengers on board, children become part of the ship’s family and are generally well-behaved.

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