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July 11, 2018

A First-Time Cruiser Falls in Love with Island Windjammers’ Caribbean Adventure (Part 2)

By Elysa Matsen Leonard.

Island Windjammers’ Caribbean Sailing Adventure

If you want to know what an Island Windjammers Caribbean Sailing Adventure 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.

Read Part 1 of Island Windjammer’s Caribbean Adventure here.

Island Windjammers' Caribbean Sailing Adventure

The three-mast Vela is a beauty alright! * Photo: Elysa Matsen Leonard


Part 2

Day Three: Oui Oui

Again, we woke up in a different port. Today, it was Iles de Saintes, a small island off the coast of Guadeloupe. I went with another passenger friend, Chris, to meet the dive operator that operations manager Jess kindly researched and recommended, “La Dive Bouteille – Plongées des Saintes.” Others went to shop in the village. Since we didn’t speak French and the French couple who ran the outfit spoke little English, it was a bit challenging above the water, but once below, we were all on the same page.

Island Windjammers' Caribbean Sailing Adventure stops in st lucia with people getting ready to dive

Getting ready to dive in St. Lucia. * Photo: Elysa Matsen Leonard

The diving was rich with all types of hard and soft corals and thankfully no signs of bleaching. All the usual suspects of an Atlantic coral reef were there, from sand divers to porcupine puffers, blue-headed wrasse and spotted moray eels. If you listen carefully to the audio you can hear me squeal with delight upon seeing a pair of puffer fish.  Above a sandy patch, we saw a mystical garden of small dancing eels and jawfish that hover over their holes and once they see your shadow disappear into the sand.


Our dive guides were experts on this reef and loved showing us their special place. We snacked on tea and madeleines on the dive boat between our dives, and it was one of those days where you breath deep, recognize the beauty of the sea and are just thankful for the experience. Back on board with our Vela-mates, we all hopped in the dinghy for some afternoon shopping and that evening, we took one more dinghy ride for a drink at a local café.


Day Four: Beach Paradise

The night before, Vela had moved on to another small island off the coast of Guadeloupe, Marie Galante. We had our own private and gorgeous sandy beach for swimming and snorkeling. The water temperature was perfectly inviting and there were areas for sunning and for shade. As our dinghy approached the island, we felt like we were on “Survivor!” — only we didn’t have to worry about food, shelter or competing for any immunity idols.

Island Windjammers' Caribbean Sailing Adventure cruise ship Vela on the ocean

Serene Marie Galante Beach. * Photo: Elysa Matsen Leonard

A delicious lunch from Vela was brought to us via the magic dinghy — “cheeseburgers in paradise” with breadfruit fries. It was a perfect day. I snorkeled looking for seahorses in the grassy bay and was surprised to find a few starfish and a baby queen triggerfish who was sheltering near a large conch shell. That night we sailed from the small cluster of islands surrounding Guadeloupe to Martinique.

Island Windjammers' Caribbean Sailing Adventure sets out home made meal

Viola! And there was lunch brought to us on the beach by our awesome crew; * Photo: Elysa Matsen Leonard

Day Five: Snorkeling as Good as Any Diving

Our day in Martinique began with a visit to the small quaint seaside town of Saint Pierre. This village was completely destroyed by the eruption of Mount Pelee in 1902, the worst volcanic eruption in the 20th century that killed some 30,000 people.

We had a choice of touring a rum factory or going into town and visiting the ruins from the volcanic eruption. I chose the latter and accompanied by my Bostonian friend, Joanne, who had become a close friend at this point, we explored the ruins and enjoyed a stroll through the picturesque seaside village. There were many small cafes and quaint French shops, and we indulged in coffee and pastries while we soaked up the views.

Island Windjammers' Caribbean Sailing Adventure

Vela reaches Martiinique. * Photo: Elysa Matsen Leonard

We returned to the ship and in the afternoon sailed over to a small swimming beach called Anse d’Arlet. Jess told us there was amazing snorkeling there, though when I saw the location and the large cluster of people in the water, I had my doubts. I had become the snorkeling leader, at this point in the trip since people began to figure out that I knew my fish. Turns out, the snorkel was outstanding and I was very happy to teach fish ID’ing for the afternoon. Our snorkeling stint was as good as any dive, with great numbers of a diverse population of fish, even an octopus.


Day 6: All Good Things Must Come to an End

Overnight we had sailed back to St. Lucia and into Rodney Bay, north of Marigot Bay, where we would spend our last day. One of the interesting excursion choices was an off-road Segway tour. I wasn’t sure I would be good at this but thought that on the last day I should break out of my comfort zone. I found out Segway riding requires no skill and it was just a ton of fun.

Island Windjammers' Caribbean Sailing Adventure with sailors on a segway tour on st lucia

The view was to die for! * Photo: Elysa Matsen Leonard

We took a bus to the drop-off location and our guide led us up a mountain for gorgeous views and taught us about plants and history along the way. At the top of the mountain, we had drinks and snacks and then headed back down to a beach bar and then back to the pier for those who wanted to get back to the ship for lunch. Me? I just had to do one more dive! I saw that there was a scuba company doing shore diving — which means you don gear at the beach, walk into the water and swim from the shore to a dive location, in this case, a shipwreck.

The dive guide took me out to the wreck and we saw a school of squid, three types of moray eels, and all my fish friends. I was wearing the wrong dive boots with my fins and ended up with blistered feet, but it was well worth the pain.

Overall, the islands we visited had excellent diving and snorkeling opportunities to explore a spectacular coral reef environment. More on this later, stay tuned!

Island Windjammers' Caribbean Sailing Adventure view underwater of an eel

We spotted a snake-like moray eel! * Photo: Elysa Matsen Leonard.

Our Last Evening

That night was our last evening together on Vela. We could have gone to a fish fry event on St. Lucia, but it was a unanimous decision to spend our last night together on the ship with our week-old Vela family. We played a raunchy laughter-filled round of “Cards Against Humanity,” as we swigged our beer and wine, that was made more fun since our 90-year-old patriarch decided to play and drink along; ever the good sport. We could see how he made it to 90 in such good shape and spirits. That evening on deck playing cards was a great ending to a beautiful week.

Island Windjammers' Caribbean Sailing Adventure with cruisers playing the game cards against humanity

Eric playing along! * Photo: Jess Benson

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PROS & CONS in a Nutshell

I loved ….
  • Gorgeous sunsets from the deck.
  • Unexpected double rainbows from the ship’s deck.
  • Food – Chef Lenny was amazing, a Caribbean twist and all food cooked from scratch and seconds were always available.
  • Dining al fresco on the deck of Vela.
  • Our own private beach; think Survivor but with awesome food and no competitions or immunity idols necessary.
  • Snorkeling is the best ever in some surprise locations, as good as any boat dive.
  • Dinghy Rides. Loved this mode of transportation, we could go anywhere — or so it seemed!
  • Meeting friends for life and connecting with great people.
  • Internet service slim-to-none for most of the cruise – you won’t be able to get online often with a clear connection (PRO & CON! )
But ….
  • Seasickness.  No joke, take the medicine.
  • Sunburn.  Also, no joke, wear 30 SPF (reef-friendly) sunscreen, hats, and sunshirts; thankful for the ship’s shady tarp!
  • Food.  Although it was amazing this is not one of those cruises where you get 1,000 choices on the menu. This was fine for me, and make sure it is for you too. If you have severe allergies, this is not the cruise for you. If you have minor dietary concerns, they can accommodate small requests.
  • The drive to and from the airport is an hour away and the roads are narrow and windy and the cab drivers are a bit crazy; stay calm and enjoy the ride.
  • Traveling to St. Lucia takes a full day so plan extra time to get there before you leave on the cruise; you need to give yourself at least one extra day.
  • Excursions. You won’t have a ton of choices, but this cruise is to enjoy, relax and do nothing at all or a few things if you want. It’s laid-back relaxation.
  • I can’t lie.  I’m having trouble coming up with any more, it was amazing and I sure hope to go again!


Island Windjammers' Caribbean Sailing Adventure view of the ship from aboard the dinghy in the water

Our beloved dinghy. * Photo: Elysa Matsen Leonard


And Last but Not Least … My Crew Crush

You will be spoiled by the crew. From Bernard who figured out early on that that I needed three cups of coffee to function and start my day, to Chef Lenny who would let you have seconds of your favorite dishes and Stephen, our steward, whose laughter would instantly spread to whomever was nearby. Jess, the ship’s operations manager (aka cruise director), made sure we each did everything we wanted to do, including my diving, no matter how much time it took to arrange and set up. The captains and engineers worked tirelessly to make sure that we had a seamless and excellent trip, and the captain still managed to eat several meals with us during the week.

Island Windjammers' Caribbean Sailing Adventure crew aboard the ship Vela

Island Windjammer’s Vela Crew. * Photo: Elysa Matsen Leonard

The crew all seemed to have a similar integrity, passion, and love for what they do. Many shared stories about their life at sea and on the islands — Chef Lenny, from the island Nevis, admitted although he cooks and lives on a ship for a living, he doesn’t know how to swim and doesn’t even like the water. LOL!


Quirky Cruise is the small ship cruise expert. Whether you’re a veteran on the water or exploring the idea of becoming a seafaring fellow you won’t want to miss out on your chance for your own personal adventure! Your own small ship sailing adventure is a click away. Don’t miss a post, subscribe to HERE for monthly updates! 


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Posted In:

Caribbean Islands, Sailing Feature Articles, West Indies


  1. Leighton Simmons - 2 years ago

    Couldn’t agree more!!! Last November was our first time cruising as well. Was fortunate enough to have won it, via kirk and sweeney rum company. We loved it so much that We’ve already booked another trip this November (2018), to get married aboard.

    Our TRip was slightly altered due to the devastation from the HURRICANEs last year (2017), but the flexibility of the Vela and crew was amazing! We were practically given free run of the cruise and where we wanted to go. Try getting that on a larger cruise….

    We’re so looking forward to the next adventure and seeing whom else we MEET. You weren’t kidding about making friends and The crew. We met people who will more than likely be lifelong companions.
    Can’t SAY enough about the company and their PROFESSIONALISM.

  2. Quirky Cruise - 2 years ago

    Thanks Leighton! We agree, island windjammers is awesome and one-of-a-kind! WOuld be great if you could fill out a reader review for us (think trip advisor for small ship cruising!). Thank you 🙂

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