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Meet a few of the windjammers’ crew!

The crew of the Schooner Stephen Taber, looking sharp!

Small ship cruises have become more and more popular these days as travelers realize they want a stronger connection to the people and places where they visit. Well, with only 20-35 guests per cruise, the Maine Windjammers are certainly small ship cruises, and heartfelt hospitality has been the cornerstone of Maine Windjammer sailing trips since they first started in the ’60s.

This hospitality comes not just from the owners and captains but from the crew members as well. Crew is hired not just for their sailing or cooking skills but also their desire to connect with guests. “It’s all about the people,” says Captain Barry King of the Mary Day, “I can teach someone to sail, but we’re in the people business. I need people who love people.”

Crew members see to every detail aboard the ship. From welcoming guests aboard, to making sure they’re comfortable in their cabins, to pointing out wildlife and rowing guests ashore for an afternoon exploratory hike on an uninhabited island, friendly crew members are essential to the windjamming experience. That’s why captains are looking for bright and friendly people from all over the country who can put guests at ease, brighten someone’s day and make for smooth sailing.

As this year’s crew members start arriving this April we thought we’d take a moment to introduce you to some of them. They’ll be going out of their way to make your Windjammer vacation the trip of a lifetime.

Chef Bradley Jennings, Windjammer Angelique

Chef Bradley Jennings aboard Windjammer Angelique
Rick Lewis Chef Bradley Jennings aboard Windjammer Angelique

This will be chef Bradley Jennings’ third year cooking aboard the Windjammer Angelique. After spending years working in the restaurant and hospitality industry, he was ready for a new experience. His quest led him to cook out west on trail ride expeditions and then out here to Maine to cook on Angelique.

He grew up in Tennessee, nowhere near boats or water, and was immediately enamored with windjamming, realizing it was the adventure he didn’t know he had been looking for.

“It’s such a unique experience for both hosts and guests” he says “and as close as you get to pure unindustrialized hospitality. As a crew member who lives on board all summer, you are literally sharing your home with the guests…It’s something that I take a lot of pride in.”

“For me,” says Bradley, “cooking is my way to contribute to the experience, both for the guests and the rest of the crew. I like to find extra little things I can do to exceed expectations.” 

Beth Sailor, Deckhand, Schooner Heritage

Beth is from Indiana from a family that has a love for sailing. Her grandfather was in love with sailing ships and at the close of WWII begged the Navy to allow him to crew on what is now the USCG Barque EAGLE. Though he was denied, he kept his love of sailing and passed it on to multiple generations.

Sailing has been a fascination of Beth’s before she ever left land-locked Indiana. Beth was a guest aboard Heritage in the 2021 season. The Captains sailed the ship pretty hard and the adrenaline and joy she found in it convinced Beth that she needed to come back and crew the following season. “Now the ship owns me!” she says.

This will be Beth’s second season sailing aboard the Schooner Heritage. She enjoys the ever-present challenge that sailing presents. There is never a day that doesn’t present you an opportunity to learn and build skills. Conversely, she loves the small moments that one finds such as the quiet mirror calm in the mornings, or watching the stars against the shadowy masts while swaying at anchor.

Chef Anna Miller, Schooner Ladona

Chef Anna Miller aboard Schooner Ladona
Leigh Doran Chef Anna Miller aboard Schooner Ladona

This is Anna’s 8th summer cooking on Ladona and her 20th season cooking on a Windjammer! She came to Camden the summer before her last year of culinary school looking for a cooking adventure – not knowing what she was getting into or if she got seasick (She doesn’t! And it’s actually very rare for guests on these boats to get seasickness because our sailing waters are so flat!).

“I love it,” says Anna. When asked what she loves most about being aboard she replied, “I love meeting all the people that come, hearing the stories of how people ended up in the ‘middle of nowhere Maine’,” and how they decided to take the leap of making this their vacation experience.”  And, of course, “there’s always something new and pretty to look at”

Anna enjoys the creativity of cooking on board Ladona, “I’m always doing something different and all summer long I maybe repeat five or six dinners throughout the season.” It’s a lot of fun.

Anthony St. Pierre, galley hand, Schooner Grace Bailey

Quinton Donleavy Crew member Anthony St. Pierre aboard Victory Chimes.


Back for his second year of windjamming is Anthony St. Pierre.  He worked aboard Victory Chimes last year and followed Captain Sikkema to Grace Bailey this year. “Call me Dishmael” he writes, “There’s no one road by which a man finds himself at the sink of the Victory Chimes, up before (or in tandem with or possibly slightly after) the sun to man the handles and the twin steel drains, fraught with the caprice of scalding waters…”

Raised on a dairy farm in Vermont, he first came to Rockland a 33 year old social worker, absent any sailing knowledge, to fill in as a galley-hand for one week, following in the footsteps of one of his good friends.

I’ve been told my coming here on a whim, leaving a job of 10 years, is very “character in a novel.”  Well, I am a novel character, of a sort. I enjoy bad puns and coming up with impromptu lyrics… I write poetry occasionally, I try to see the good in everyone, I listen to Gordon Lightfoot frequently, I love being in nature and talking about my family.”

“It’s been absolutely worth breaking my established rhythm for the opportunity to be here…At my age, it’s no exaggeration to say that that one week as a relief galley hand changed the course of my life; I felt so at home here that I dropped everything I’d ever known (except the combination attic/garage load in my car) to be here an entire season. Three months of laughter and fond memories with new friends later, and my gratitude just keeps a-growing. “

contributor: Meg Maiden


Categories: Behind the Scenes, Cruises, Fleet, Maine Windjammers

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