A First-Time Cruiser Falls in Love with Island Windjammers Caribbean Adventure (Part 1)

Island Windjammers Caribbean Adventure

By Elysa Matsen Leonard

Updated September 2024

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.

RELATED: Here’s Part 2 of Elysa’s Adventure.

Meeting My Shipmates

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.

The first people I met were a lovely 50-something couple from the San Francisco Bay area, Kathy and John, who were celebrating a milestone anniversary. And there was Joanne, a wickedly funny single woman from Boston cruising for her 60th birthday. Another single traveler from Wisconsin, Kristen loved the freedom of solo travel and was an experienced Island Windjammer. She loved this type of cruise even though she was prone to sea sickness — she wore the patch and sailed on.

To my surprise, there was a couple from Annapolis, near my home in Ashburn, Virginia. Bryan and Beth were both 50-ish with busy corporate jobs. They lived by the sea and loved small ships. I spent lots of time laughing with them and talking about our next adventures.

The whole gang! * Photo: Elysa Leonard

We were also joined by a family of nine from the west coast, with a spunky 90-year-old patriarch Eric. His son Greg had arranged the trip as a tribute to a sailing they had made as a family into Marigot Bay some 50 years back. I can’t lie, I was a bit concerned about how he would fare on this trip. Turns out the spry nonagenarian more than held his own; he was clearly born with sea legs and took it all in stride.

Eric was a retired engineer who had at one point years ago left his job, bought a boat similar to Vela, and took his family on a Caribbean sailing adventure. The tall strong man with a sweet demeanor shared stories with anyone who would listen.

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.

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The Vela Backstory

Before Island Windjammer passengers ever entered the picture, Vela had a story of her own. The three-mast, 156-foot-long sailing schooner had been a medical-support vessel sailing around the Marshall Islands. She was named Tole Mour, which means “gift of life.”

Vela then became part of the Catalina Island Marine Institute and offered sailing training, oceanography and marine biology education for hundreds of school-aged kids. She was purchased by Island Windjammers in 2014 after the ship was discovered in California by Captain Nervo Cortez, the line’s fleet captain and a man who radiates a humble confidence in all he does.

He was onboard my cruise along with Captain Alexis. Nervo Cortez sailed the ship 4,500 nautical miles from California through the waters of five countries and through the Panama Canal, to St. Vincent and then Grenada, where the ship was refurbished before her first sailing out of St. Lucia.

It was renamed after the constellation, Vela, which also means “sail” in Italian and Spanish. Today it’s the largest of the line’s trio of ships.

Day 1 — Velacoladas & Mal de Mer

The cruise started and ended in Marigot Bay, St. Lucia and we visited at least one new place each day, sometimes two. Our Uber for the week was a dinghy. Dinghies got us between the ship and shore with some dry and also some wet landings right on to the beach.

We easily adapted to this mode of transportation, donning our life vests and hopping aboard; even our 90-year-old passenger seemed to master this with ease. Our dinghy trips were one of many sources of humor; though it didn’t take much to get us all giggling.

Our first day was spent in St. Lucia, and we traveled from Marigot Bay to Soufriere where we did a late afternoon snorkel at the Anse Chastanet Resort Marine National Park.

The water was a bit choppy and we were slowly losing daylight, but we saw several black and white spotted drum fish, iridescent blue chromis, several species of grunts, and some stoplight parrot fish. It was just a glimpse of the amazing snorkeling to come.

At sunset each day was happy hour, with snacks and the signature drink, the Velacolada, a delicious concoction of rum, pineapple and coconut — not too sweet or too strong. I still crave this drink at about 6pm every day, even weeks after I’ve returned home.

There was also a refrigerator filled with soda, beer and wine for consumption 24/7, as well as ice-cold water and iced tea. Beer and wine are included in the fare as well as mixers for other types of drinks; passengers are free to bring their own spirits on board.

Elysa with new friends Beth & Bryan. * Photo: Elysa Matsen Leonard

Meal time that first evening was inside, as it was a bit too windy to eat out on deck. Our favorite dinners and happy hours over the course of the week were outside on the deck at several tables set up under a shady tarp. Some perfectly timed rainbows and sunsets were the icing on the cake.

In this intimate setting, it didn’t take long for 16 passengers and 10 crew members to become fast friends — one big shippy family.

Vela’s indoor dining saloon. Outdoor dining was also offered, weather permitting. * Photo: Island Windjammers

During the week we had some excellent meals served by the ship’s stewards, Bernard and Stephen. If someone requested seconds or a special order, they always responded with a smile and a “no worries.”

Favorites included pork tenderloin with a compote of apples and red onions, local fish, barbecued ribs and chicken, and eggs benedict for breakfast. With each meal there was a Caribbean twist.

For instance, the “cheeseburger in paradise” was accompanied by coleslaw and fries, but these fries were made of breadfruit, not potatoes, and they were delicious. The tuna salad one day was really delish, and when I asked Chef Lenny why it was so tasty, he answered: “I added some island secrets.”

The desserts were show stoppers too, especially a soursop fruit sorbet and to-die-for cheesecake drizzled with caramel that was so good passengers begged for seconds.

Chef Lenny. * Photo Joanne Hutchinson

Rockabye Baby

The ship began to sail after dinner, traveling at night so we could spend our days on shore. Sailing between islands, as opposed to the calmer seas along the coast, meant open seas and some choppy waters.

I was one of the luckier ones. I love the churn of the ocean and have never been seasick on the many small boats I’ve been on. My Vela cruise confirmed this. However, many other passengers quickly found out the first night that they were not so lucky.

The “mom gene” kicked in, and I spent the night handing out Ginger ale. Anyone prone to motion sickness and for those who don’t know if they are: definitely bring sea sickness meds (like Dramamine and/or a prescription patch) and use them before things get rocky.

A cozy Vela Staysail cabin. * Photo: Island Windjammers

Day 2 —  Sea Legs Return

As people got their sea legs back on day two, the fun resumed. There were rainbows, lots of sunshine, crystal blue waters in shades I’ll never forget, amazing snorkeling, diving and relaxation. Snorkeling equipment is complimentary as are several paddle boards and floating mats, plus dinghy trips to and from the islands for walks and hiking etc.

The idea on an Island Windjammers Caribbean adventure cruise is to reeeeeelax so days are not heavily scheduled and sometimes passengers choose to just chill on deck.

Serenity approaching Dominica. * Photo: Elysa Matsen Leonard

Day two was the island of Dominica. They were hard hit by Hurricane Maria last September, and are still recovering — we saw downed trees, closed bridges and roofless buildings everywhere. A few excursions are offered in most ports, and in Dominica, we had the choice of an island tour or just a walk around the beach and town. I chose the island tour for $40.

Our driver, Winston, was a proud man and told us of their progress and setbacks throughout the tour. He gave us a mental picture of a green lush Dominica that was known for exporting fruits and vegetables before this category 5 storm wrecked its havoc. At the end of the tour, despite the destruction, we would learn the secrets of chocolate making. (See my follow-up article for more on that!)

That night we left Dominica for Iles des Saintes, where I would spend a gorgeous morning scuba diving. More on that later as well!

Elysa and her new friend Eric. * Photo: Elysa Leonard

Quirky Cruise is the small ship cruise expert so first-time cruisers needn’t worry!

Read our answers to questions about small-ship cruising on our FAQ’s page and then learn more here about the differences between big ships and small ships besides their size. 

Check out PART 2 of Elysa’s adventure.

Interested in an Island Windjammers Caribbean Adventure?

Check out availability and fares at IslandWindjammers.com.

Prices include all meals; wine, beer and afternoon rum punch (you can also bring your own spirits!); snorkeling gear to borrow; and lots of fun.

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