Island Windjammers Review — A Week in the Caribbean on the Cozy Diamant Sailing Among the Grenadines

Island Windjammers Review

By Amy Fried

Standing barefoot on the teak deck of the Diamant, with nothing but the open sea ahead and a gentle Caribbean breeze swirling around me, I felt a world away from the crowds and glitz of a traditional cruise.

This isn’t a cruise for those seeking infinity pools or onboard casinos; it’s a journey for travelers who want to feel the wind in their hair, the salt on their skin, and the camaraderie of a tight-knit group of adventurers.

Island Windjammers’ Diamant, a 101-foot schooner, is a floating oasis of simplicity and charm.

With just five cabins and a maximum of 10 passengers, it’s intimate in the best way possible.

From our first day aboard in Grenada to the final sunset sail back six days later, the Diamant brought us closer to the sea, the islands, and each other.

New friends chilling on deck. * Photo: Amy Fried

The Ship: Intimate and Inviting

Diamant is not your typical cruise ship. With its polished teak deck, classic sails, and warm wood interiors, it feels more like a private yacht than a commercial vessel. The ship’s small size means every corner is a shared space (except your cabin of course!), from the cushioned benches on the top deck to the cozy dining area indoors.

VIDEO: Here’s a look at the Diamant’s main deck space.

The cabins, while compact, are thoughtfully designed with en-suite bathrooms, portholes and comfortable beds.

There’s one Owners Suite with a queen-sized bed and separate sitting room; three Navigator Cabins have a double lower bed plus a single upper berth (like one in video below), while one Navigator Cabin features only two lower singles.

VIDEO: Below is a tour of one of Diamant’s five cabins, #5.

My favorite spot was the open-air covered back deck, where passengers gathered for snacks, drinks, and storytelling under the stars.

The Diamant has a timeless charm. It’s a ship that invites you to unplug, relax, and connect with your surroundings.

Day 1: Setting Sail from Grenada

Our adventure began at the Knife & Fork restaurant in Grenada, where we first met Captain Todd, a seasoned mariner with an easy laugh and a knack for storytelling.

Alison and Captain Todd. * Photo: Amy Fried

Over the course of our six-night cruise, he became our entertainer, cruise director, sailing instructor, and an all-around great person to be around.

As he led our group of seven passengers past the sleek mega-yachts moored in the harbor, the Diamant stood out with its warm wood detailing and classic lines. She felt approachable, unpretentious, and entirely different from her flashy, fancy-yacht neighbors.

Once aboard, we were instructed to toss our shoes into a box that was quickly whisked away. With that, our group of seven quickly shed more than footwear — we left behind the formality of everyday life.

The indoor dining area, featuring two U-shaped seating areas, a mini fridge, and a popcorn machine perched in one corner, became our central hub. Captain Todd outlined the plan for the week: we’d decide together where to stop, when to snorkel, and how to spend our days.

The indoor dining area. * Photo: Amy Fried

After a five-hour sail to our first anchorage of Ronde Island, a private, largely uninhabited island 10 miles north of Grenada, the group settled into the ship’s rhythm.

My travel companion Alison dove off the side of the boat for a swim, while the rest of us relaxed on deck with our first rum punches.

View of beautiful Ronde Bay. * Photo: Amy Fried

RELATED: Here’s a review of Diamant’s fleetmate, the 26-pax Vela.

Food and Drink Aboard the Diamant

That first night, and on others, dinner was served under the stars — a bowl of rich, green callaloo soup followed by peppered pork slices with orange sauce, mashed white sweet potatoes, and perfectly cooked vegetables. A slice of chocolate cake rounded out the meal.

Every meal aboard the Diamant felt like a small celebration. Chef George, working in the ship’s compact galley, created dishes that were hearty and delicious.

Breakfasts included classics like French toast with bacon or ham and cheese omelets, served alongside fresh fruit platters of watermelon, pineapple, and oranges.

Lunches were light but satisfying, featuring dishes like salads, pasta and cheeseburgers with fries.

Tasty lunch. * Photo: Amy Fried

Dinner was the highlight of each day. From shrimp scampi to lobster, barbecue ribs, and mac and cheese, every meal was thoughtfully prepared and tailored to passengers’ preferences (for example, if I wanted a big salad for dinner instead of pasta, the chef was happy to accommodate).

Lobster night, yum! * Photo: Amy Fried

Happy hour snacks appeared each afternoon. Dessert ranged from rich chocolate mousse to key lime pie, always served with a smile and a story.

Alcohol and soft drinks are included in the price. There’s always a cooler full of Carib and Stag lager at the ready, and rum punch is always available in the mini fridge. Carafes of red and white wine are served at dinner.

Guests are welcome to bring their own alcohol on board and mixers are on hand.

Enjoying a beer in the Caribbean sea! * Photo: Amy Fried

Day 2: Snorkeling and Sandy Island

The first full day aboard started with French toast, scrambled eggs, and crispy bacon served by everywhere-man Bolo and paired with family-style platters of fresh fruit.

Bellies full, we took a short tender to a snorkel spot a few minutes from the ship in Ronde Bay. Captain Todd had rated the coral “a 5.5 out of 10,” but the abundance of marine life made up for it. (Sadly, many of the Caribbean’s coral reefs are damaged or dead due to climate change, pollution and rising ocean temperatures.)

Snorkeling highlights included a spotted boxfish with its kitten-like saucer eyes, colorful angelfish, and even a sea turtle.

Anchored off Ronde Bay; it was a short tender ride to some great snorkeling. * Photo: Amy Fried

Throughout the week, we found the snorkeling to be very good, with crystal clear waters and great visibility.

By late morning, we set sail from Grenada. Captain Todd tendered to customs on shore to check us out of Grenada while we enjoyed a lunch of chicken wraps and bean salad.

Within 90 minutes, we were anchored outside of Carriacou, an island in the Grenadines, and Captain Todd gave us two options: a visit to Sandy Island, a tiny, uninhabited strip of sand surrounded by turquoise water, or the Paradise Beach Bar on Carriacou.

Karen and Tom chose to get dropped off at the Paradise Beach Bar. Alison and I chose Sandy Island, where we swam, snorkeled, and relaxed with a cooler of drinks and beach chairs set up by the crew.

The simplicity of the setting was a reminder of why we came on this cruise: to escape and unwind. The snorkeling around Sandy Island was fantastic with tons of sea life.

Sandy Island off of Carriacou. We stopped here twice; once on the way from Grenada, and once on the way back to Grenada. * Photo: Amy Fried

Back on board, happy hour snacks appeared at 4:30 pm — freshly fried crunchy plantains, deviled eggs, and fresh mango slices. Dinner was peppery shrimp scampi with steamed zucchini, rice, and key lime pie for dessert.

The night ended with a briefing for the next day, filled with laughter and plans for more exploration.

Day 3: Exploring Union Island and Chatham Bay

Breakfast was a ham and cheese omelet served with bagels and the usual spread of fresh fruit. We spent the morning on a 90-minute sail toward Union Island, whose jagged silhouette juts dramatically from the sea.

Union Island. * Photo: Amy Fried

We anchored off Frigate Island for snorkeling, where I spotted a school of squid swimming in perfect formation, their big fake eyes making me laugh. Other sightings included a sea turtle, rainbow parrotfish, and a spotted trunkfish.

Lunch brought a refreshing mix of tuna salad, pasta salad, and homemade oatmeal cookies drizzled with caramel for dessert.

After a 30-minute sail, we arrived at Chatham Bay, a peaceful spot surrounded by lush hills. While some of our shipmates hopped onto the ship’s inflatable raft, Alison and I decided to snorkel to shore, where we found a makeshift beach bar run by two friendly locals.

The underwater sights at Chatham Bay were incredible — turtles, spotted eagle rays, a stingray, and schools of vibrant fish gliding near the rocky shores.

Diamant’s fun inflatable, here near Chatham Bay, where Alison and I snorkeled to shore to explore the rocky coves. * Photo: Amy Fried

Back on board, happy hour snacks included freshly fried tortilla chips and slices of fresh tuna sashimi, caught by the crew right off the ship. Dinner that evening was a barbecue feast: ribs, mac and cheese, rice and beans, and stewed zucchini with tomatoes.

Fresh caught sashimi tuna for happy hour snacks. * Photo: Amy Fried

Day 4: Mayreau and Saltwhistle Bay (and shoes!)

Breakfast today featured fried eggs and corned beef hash, a classic but polarizing dish among the group.

Donning shoes for the first time this week, we anchored at Saline Bay on Mayreau, one of the smallest inhabited islands in the Grenadines.

From there it was a 30-minute walk up and over the island’s one road to Saltwhistle Bay, a stunning crescent of white sand and turquoise water. This idyllic spot felt like paradise.

Stunning Saltwhistle Bay. * Photo: Amy Fried

I spent hours perfecting my sidestroke in the warm, crystal-clear water. It was nice to catch a glimpse of local life after spending the last three days with only the beautiful Caribbean, its underwater inhabitants, and our fellow passengers as company.

Lunch was tender pork slices in gravy with a side of potato salad and steamed cabbage, followed by a rich chocolate mousse.

The 40-minute sail to Tobago Cays during happy hour was a highlight, with golden light reflecting off the water and laughter filling the air.

Snacks included lobster pizza and freshly fried plantain slices, a perfect prelude to a hearty dinner of beef in dark gravy with mashed potatoes and steamed vegetables.

A Flexible Adventure

The Diamant’s itinerary strikes a perfect balance between planned stops and spontaneous exploration.

Each day brought new snorkeling spots to explore, from the pristine beaches of Sandy Island to the vibrant underwater life of Tobago Cays. The small group size meant we could decide as a team how to spend our days, whether snorkeling, visiting a beach bar, or simply relaxing on deck.

Fun in the sun in Tobago Cays; chairs and a cooler were brought over on the tender and set up by Kevvie. * Photo: Amy Fried

Captain Todd’s flexibility allowed us to experience the Grenadines in a way that felt personal and unhurried. Whether it was a tender ride to a deserted beach, or an afternoon spent floating on the ship’s inflatable raft, every moment felt tailored to our interests.

The most crowded place we visited; near Tobago Cays. * Photo: Amy Fried

That said, on this itinerary, as on many offered by Island Windjammers, there were no optional organized guided excursions offered, which suits some folks just fine. However, if you like guided tours, the Island Windjammer itineraries that visit St Lucia, Dominica and Bequia offer a few optional choices.

The Crew: The Heart of the Ship

The crew of the Diamant deserves its own round of applause. Captain Todd kept us entertained with tales from his bush-piloting days, while Chef George worked magic in the galley, serving up meals that catered to all tastes and dietary preferences.

First Mate Bolo seemed to be everywhere at once, always with a smile and a helping hand. Kevvie, a new trainee, and Marlin, the engineer, rounded out the team, each bringing their own warmth and humor.

Roy, with a dry demeanor and a straight face, expertly ran the tender and helped out around the ship. His quiet efficiency and subtle humor added to the crew’s dynamic.

What stood out most was their genuine care and easy camaraderie.

By the second day, it felt like we were part of a family, not just passengers on a ship.

The Passengers — Veteran Sailors

Every other passenger aboard the Diamant had taken at least six previous trips with Island Windjammers and had already booked their 2025 adventure. Their loyalty was palpable, and their enthusiasm infectious. Three passengers had even sailed together on a different itinerary previously.

Karen and Tom (Boston natives): In their 60s and 70s, Karen and Tom were quintessential Bostonians, complete with thick accents. Tom had been in the carpenters’ union before becoming an “advance man” for presidential nominee tours, including work with President Clinton and the Kennedys. His stories, shared over dinner, were both fascinating and hilarious. He was a jokester, too — pretending his tooth fell out at dinner and placing a piece of coral on his plate for dramatic effect. Karen, who managed Boston’s largest singles bar for 40 years while raising kids as a single mom (before marrying Tom), was just as impressive. Her energy and wit matched Tom’s, though she let him do most of the storytelling.

Jennifer: A marketing executive for a global pharmaceutical company, Jennifer was navigating the recent loss of her mother. In her 50s, she brought both warmth and poise to the group, and we offered hugs and support where we could.

Leah and David (South African couple): Married since their early 20s and now living in Minneapolis, Leah and David were in their 50s and 60s. Leah was inspiring, having transitioned from being an MRI technician to becoming a commercial airline pilot in her 40s. Now a flight instructor, she shared her love of planes and their newly purchased second home on the beach in Panama.

The whole gang — guests and crew. * Photo: Amy Fried

Day 5: Swimming with Turtles and Frigate Island

After a breakfast of scrambled eggs, sausage, and pancakes, we headed to Tobago Cays Marine Park, a protected area known for its turtle population and sandy beaches. The park features a roped-off turtle sanctuary, where guests can snorkel and observe these graceful creatures in their natural habitat. I was thrilled to spot five turtles gliding through the water.

Pretty Tobago Cays. * Photo: Amy Fried

Next, we tendered to a nearby beach for more snorkeling. This spot was bustling with vibrant marine life, and the mix of corals and fish made it one of the best snorkeling stops of the trip. Under the shade of a palm tree, our small group of seven cozied up together, enjoying the view while dozens of passengers from a larger cruise ship spread out along the beach.

Lunch back on board was a fun nod to Jimmy Buffett’s classic, “Cheeseburgers in Paradise,” complete with fries. My veggie burger was delicious after the morning’s swim.

In the afternoon, a quick 40-minute sail brought us back to Frigate Island for more snorkeling off the tender. The water was clear, and the reef was teeming with schools of fish.

Happy hour snacks featured Caribbean-style pigs in blankets, a perfect bite as we enjoyed a two-hour sunset sail toward Sandy Island.

While my shipmates enjoyed a lobster dinner, I opted for a crisp romaine salad with bacon crumbles, a lighter option after several days of hearty meals.

So many lovely sunsets enjoyed from the decks of the Diamant. * Photo: Amy Fried

VIDEO: The breezy scene on deck while sailing the Grenadines, below.

Day 6: Snorkeling and Return to Grenada

Our last full day began with an excursion to the Underwater Sculpture Park near Sandy Island.

This unique snorkeling site features submerged statues, creating a fascinating blend of art and marine life. Alison and I later returned to Sandy Island for one last round of excellent snorkeling. As always, the tender crew provided chairs, a cooler, and flexible pickup times, making the outing as relaxed as possible.

As was the case with every other day of our trip, we had perfect weather — low 80s, sunny skies, a gentle breeze, and no rain or strong winds.

Afterward, we began the five-hour sail back to Grenada, soaking up the last moments of open sea and camaraderie.

Soaking up the ocean views from deck. * Photo: Amy Fried

That night, we anchored just outside St. George’s, where the lights of the town sparkled against the dark water.

The next morning, the Diamant motored into port, and we disembarked with bittersweet feelings, grateful for the incredible journey we’d shared.

Excursions… or Lack of Them

One of the unique aspects of this itinerary is the absence of organized excursions. Instead of pre-planned outings, your daily adventures are casual and spontaneous, guided by the crew’s recommendations and your own curiosity.

“Excursions” on this journey typically involve snorkeling in around a nearby bay or relaxing on remote beaches.

On our sailing, the only organized opportunity to spend money was an optional visit to the Paradise Beach Bar on Carriacou.

As for the two “hiking excursions” mentioned on the daily activity board during the week, the crew would point to the lone road on an island (which inevitably involved a hill), offering to take us to shore in a Zodiac if we were interested in walking up the road to the top of a hill and back.

The one day we needed shoes, to walk to Saltwhistle Bay. * Photo: Amy Fried

If you are keen to do more than snorkel, swim, and enjoy downtime on the ship, I highly recommend contacting Island Windjammers before you book to find out the details on shore excursions offered on your cruise before booking.

High-quality snorkeling equipment is assigned to each passenger on the first day, so there’s no need to bring your own. I especially loved the optional snorkel vest. If you feel even a bit nervous about being in the water, be sure to ask for one — it’s a great confidence booster.

While anchored at Chatham Bay, I asked one of the crew where we might find good snorkeling. He waved vaguely at the water around us. Determined, I sought out Captain Todd and asked the same question. He, too, vaguely waved his hand around the sea.

Undeterred, Alison and I swam the half mile to shore from the anchored Diamant, stopping every few minutes to give each other a thumbs up. Eventually, we discovered a spot rich with sea life near the rocky shore.

It became the most memorable moment of the trip, proving that sometimes the joy of finding your own way can be its own reward.

It’s also worth noting that this itinerary through the small islands of the Grenadines doesn’t offer much in the way of historic or cultural landmarks. While the islands boast stunning natural beauty, they lack the forts, museums, or cultural tours available in other destinations.

For travelers who thrive on flexibility and discovery, this unstructured approach is part of the charm. However, those who prefer detailed agendas or guided cultural experiences might find the lack of formal excursions a drawback.

Some Island Windjammers itineraries include destinations with more organized outings and historical sights, so it’s worth considering your priorities when choosing a trip. Ask questions before booking.

A company spokesperson told us: “Where possible, the crew will make any optional paid excursions or activities known to guests during their sail and will help facilitate these including, for example, scuba diving, river boat cruises or baths tours in Dominica as well as island and Segway tours in Bequia and St Lucia.”

Pre- and Post-Cruise Stays: A Tale of Two Hotels

We stayed in two different hotels in Grenada before and after the cruise. Both were about $200 USD a night, but they couldn’t have been more different.

Blue Horizons Garden Resort

The night before the cruise, we booked Blue Horizons Garden Resort. The room felt a bit musty and uninspiring, and the hotel had an almost abandoned atmosphere. Reaching the beach and restaurants required walking along a dark road without a sidewalk.

Although I usually prefer off-the-beaten-path boutique hotels, not in this case. In hindsight, I recommend staying near the popular Grand Anse beach next time as it’s more central, convenient and appealing.

Radisson Grenada Beach Resort

After the cruise, we stayed a night at the Radisson Grenada Beach Resort, right on Grand Anse beach — we loved it.

I had expected the Grand Anse main beach strip to feel overly touristy, but it wasn’t. The beach featured clear water framed by forested hills, with no high-rise buildings or pushy vendors — just pastel-colored homes scattered along the hillsides. It was pure peace and quiet.

Grand Anse beach, Grenada. * Photo: Amy Fried

We appreciated the Radisson’s amenities, including a sprawling pool with waterfalls, a jungle-surrounded hot tub and dining in their open-air restaurants. Our favorite meals were the chicken roti and the generous breakfast buffet.

Our room was comfortable and surprisingly nice for a “pool view” booking — we even had a patio with an ocean view. The Radisson was the perfect way to unwind after our sailing adventure.

No matter where you decide to stay, I definitely recommend staying a couple of nights in Grenada before and/or after your cruise. In fact, I found myself wishing we had booked another night or two at the Radisson.

Why You’ll Fall in Love with the Diamant

What makes the Diamant so special isn’t just the destinations, the food, or even the snorkeling. It’s the way this quirky cruise brings people together — barefoot, windblown, and laughing under the stars.

It’s the sense of freedom as you sail to yet another pristine island, with nothing on the agenda but to explore, swim, and enjoy.

Whether you’re a seasoned sailor or a first-time cruiser, the Diamant offers a rare chance to disconnect and immerse yourself in the beauty of the Caribbean.

And so if you’re eager to trade dress codes for bare feet and formal dining for a rum punch in hand gazing at a smoldering sunset, this is the trip for you.

Beautiful fading daylight seen through the ship’s rigging. * Photo: Amy Fried

RELATED: Read what it’s like to sail in the Greek Isles aboard Island Windjammer’s Lyra.

Hope You Enjoyed My Island Windjammers Review

Our six-night “Tropical Temptations” cruise included stops at Carriacou, Mayreau, and the Tobago Cays. Fares start at $2,800 per person.

Keep in mind, while you can expect your itinerary to roughly align with what’s published on Island Windjammers’ website, every trip is unique. The actual route will change depending on weather conditions, sea roughness, and passenger preferences.

How cool is that?

Your adventure is tailored to the moment, so that every journey is a little different from the last.

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