Sailing on The Two-Masted Schooner Pioneer

The Scottish term “to scoon” means to skim along the water.

From 1850 through the early 1900s, schooners (the foremast shorter than the mainmast), with no fuel costs, no engines or fuel taking up valuable cargo space, carried goods between coastal towns. The Pioneer (102 feet tip to tip) was built to carry sand mined near Delaware Bay to an iron foundry in Chester, Pennsylvania. She was the first of only two iron-hulled cargo ships and is the only one still in existence. In 1966, the ship was sold to Russell Grinnel Jr. of Gloucester, Massachusetts who restored the rig and rebuilt the hull with steel plating, leaving its iron frame intact. Grinnel left her to South Street Seaport upon his death.

(Photo by Richard Bowditch)

Today, Pioneer represents living history. Maritime skills, New York harbor’s history, and marine ecology are some of the things taught onboard to visitors and volunteers May through October. Participate by helping raise a halyard – a line which is used to haul sails, flags, or spars. (Tasks are designated for adults or children.) Or just enjoy the two hour sail through New York Harbor, past Governors Island and The Statue of Liberty with unique views of the Manhattan skyline and whatever else is on the water that day. Opportunities for photos are constant.

On a pretty day (or sunset sail) the trip is literally a breath of fresh air. Afloat and out of context, it’s easy to let one’s thoughts wander freely. City tension relaxes. Hold someone’s hand, experience the Oz-look of Manhattan Island through the eyes of a child, tell a story about early New York.

Our trip carried forty passengers – who found seating willy-nilly on deck – and six crew members. I spoke to trainee Alex Berman who loves sailing, is great with kids, and knows enough about her work to answer questions. As she’s still in school, Berman has no idea how her penchant for the water will fit into the future, but she’s sure it will. Alex is smallish and wirey, yet pulls and coils rope as if half again as physically substantial. She snaps to when orders are called out.

Giselle Hart (Photo by Alix Cohen)

Giselle Hart , a professional crew member, is calling orders. “I grew up around the ocean in Boston, not sailing though, that came later – to stay near water. I’ve been sailing boats like this for about six years in Maine, the Northwest… there are dozens of schooners, some newly built, some preserved over time.” You can see the pleasure Giselle takes in her job. Her movements are sure. She’s alert to sun and wind, basking in both, with a peripheral traveling eye on passengers; very much in her element.

David Sheldon is a twenty-year part-timer. He calls himself a “boat slut”, loving where he is at least a much as Gabrielle. “What if it rains?” I ask. “We won’t go out if it’s raining. Wind is not that much of a problem, though, sails can be adjusted; it’s like shifting gears. Pioneer is a very stable boat with a big flat bottom.” David is steady and nimble. He walks as if the boat weren’t moving, climbs, and hauls sail with fluency and grace. “If we didn’t tip/keel, we wouldn’t be able to turn,” he explains after a wake reaction to a passing boat. (Birds have a keel bone.) He exults in sparking water, white clouds, and the feel of spray.

David Sheldon (Photo by Alix Cohen)

Captain Malcolm Martin hails from Boston but was indirectly drawn to boats through science and mammal behavior – whales, in particular – after college. By the time he got to New York, he was already an accredited captain. “One day in 1995, I wandered down to pier 16, saw the boat and asked if I could help. They handed me a chipping hammer.” He is, to date, the longest serving captain on Pioneer.

The trainee program is one of Malcolm’s passions. “There’s nothing better than starting with someone who doesn’t know the front of the boat from the back, then watching them anticipate what has to be done. Think of the phrase ‘learning the ropes.’ Skills are handed down from person to person.”

Statue of Liberty (Photo by Alix Cohen)

No experience is necessary. Students of all ages and walks of life, hobbyists, water lovers and those headed into the profession, are taught history, knot-tieing, navigation, sail handling and “boat husbandry” = maintenance. The captain calls it “a unifying activity.” Volunteers learn to work with and trust one another as well as self reliance, skills that are essential elsewhere. “You need your shipmates to function; teamwork must be coordinated.”

A man who recently charted Pioneer for his family had been a troubled teenager when he took part in the Marine School program formerly run by the Seaport. He kept repeating how much the experience changed his life. (The more comprehensive curriculum involved taking the boat out for weeks. Malcolm hopes to bring this back.) School charters show kids that the harbor is alive with marine life by special permit fishing with everything returned to the water, “mostly no worse for wear.”

Captain Martin (Photo by Richard Bowditch)

At a roundtable meeting of Tall Ships America, Malcolm identified himself as captain of Pioneer only to discover more than half those present had been trainees here. (A tall ship is a sailing vessel with a fairly good sized mast rigged in traditional 19th-early 20th century manner.) https://tallshipsamerica.org/

Schooling begins with two four-hour, morning, instruction sails. These are followed by a conversation – what did the person get out of it, does he/she want to continue? If going further is the choice, a drug test is professionally administered as per Coast Guard dictates. This costs about $45, but is the ONLY cost to a student who may continue for years if desired. In exchange, each trainee puts in time as crew on Pioneer.

(Photo by Richard Bowditch)

I comment that despite constant handling of thick ropes I saw no use of gloves. “Gloves can get caught on things,” Malcolm tells me. “They’re meant to protect you from friction. We spend a great deal of time seeing that doesn’t happen. Gloves are a crutch, a way of doing things more casually. You quickly develop hardened surface on your hands, the hands of a sailor. It just takes practice.”

Captain Martin finds what he does immensely gratifying. He’s sailed other parts of the world but is admittedly enamored of “the beauty of the place we live in and I get to sail in.” The 137 year-old Pioneer is used for what it was designed to do – sail — not be displayed somewhere behind ropes. It’s living history.

Ninety minute and three hour educational trips are available for schools, groups, and camps. Students help raise sail, then conduct experiments in science, history, ecology, navigation, and the arts. All programs are customized. Pioneer also offers team building and corporate reset sails

(Photo by Alix Cohen)

Training, school programs and charters can be found here: https://southstreetseaportmuseum.org/visit/sails_cruises/

There’s no food or drink aboard Pioneer, but you’re welcome to bring some. Rocking and space limitation dictate it be nothing elaborate. One needs to walk a gangway and step over the side so rubber-soled shoes are suggested. Advance reservations can be made online. Check in (at the table for the docked Wavertree) at least fifteen minutes before the tour to receive boarding passes. Advance ticket sales: seaportmuseum.org/sailnyharbor.

Opening Photo by Richard Bowditch

Founded in 1967, The South Street Seaport Museum houses an extensive collection of works of art and artifacts, a maritime reference library, exhibition galleries and education spaces, working nineteenth century print shops, and an active fleet of historic vessels that all work to tell the story of Where New York Begins.

Share This Post:

Bluesky Icon Bluesky
Facebook

The re-opening of The New Museum in the heart of the Bowery brought contemporary art lovers to line up outside the expanded building that is itself a marvel of modern architecture.

Art and fashion just go together. A new exhibition at The Museum of FIT brings together an extraordinary collection.

During Women’s History Month, why not consider your own history? Author Kimber Hardick, in “An Invitation to Shine,” shares her own journey and offers tips.

Is there an AI doctor in your future? MJ Hanley-Goff attended a recent seminar to find out.

A First Encounter Two hours are hardly enough to spend in the historic Massachusetts coastal city of Salem. But when you’re only passing through, as I was, and time is limited, even a brief stay…

What’s the best way to save information for the future? You may be surprised by the answers from a technology expert.

OriginalsCBD vs SupremeCBD: The Battle of Best CBD Oil in the UK?

The UK CBD oil market in 2026 has no shortage of brands competing for the top spot. Two names that consistently appear in the same conversation among informed UK consumers are OriginalsCBD and SupremeCBD. Both brands have built solid reputations, both serve a quality conscious consumer base, and both position themselves at the premium end of the market. But when you put them side by side across the factors that actually matter, clear differences emerge

read more

5 Most Recommended Standing Desks for Very Tall People Over 6’4″ (2026)

Finding a standing desk that actually works above 193 cm feels like shopping in a market that forgot you exist. Every brand claims ergonomic design, but most frames max out 10 to 15 cm below where a 6’4″ person needs the surface for neutral wrist and elbow alignment. Desky Dual Hardwood Sit Stand Desk tops this list because its 125 cm max height, combined with a monitor arm on a 140 kg frame, gets screens

read more

Midlife Energy Reset: What Actually Helps When Diet and Sleep Stop Working

At some point, things stop adding up the way they used to. You are not doing anything extreme. Meals are fairly balanced, sleep is decent most nights, and you stay active. By most reasonable standards, everything should be fine, yet your body tells a different story. Mornings feel heavier than before, even after a full night in bed. By the middle of the day, energy drops without any clear trigger. Weekends help a little, but

read more

How To Inspect Online Body Jewelry Photos For True Quality When Shopping

Jewelry shopping online must involve attention to detail and in particular, when considering product photos. In contrast to shopping in a brick-and-mortar store, you are not able to touch the product or look at it in other perspectives. Due to this, photographs act as the main source of information regarding the craftsmanship, materials as well as the quality of the piece in general. Knowing about how to read between these images can guide you to

read more
You've loaded all available articles in this category

OriginalsCBD vs SupremeCBD: The Battle of Best CBD Oil in the UK?

The UK CBD oil market in 2026 has no shortage of brands competing for the top spot. Two names that consistently appear in the same conversation among informed UK consumers are OriginalsCBD and SupremeCBD. Both brands have built solid reputations, both serve a quality conscious consumer base, and both position themselves at the premium end of the market. But when you put them side by side across the factors that actually matter, clear differences emerge

read more

5 Most Recommended Standing Desks for Very Tall People Over 6’4″ (2026)

Finding a standing desk that actually works above 193 cm feels like shopping in a market that forgot you exist. Every brand claims ergonomic design, but most frames max out 10 to 15 cm below where a 6’4″ person needs the surface for neutral wrist and elbow alignment. Desky Dual Hardwood Sit Stand Desk tops this list because its 125 cm max height, combined with a monitor arm on a 140 kg frame, gets screens

read more

Midlife Energy Reset: What Actually Helps When Diet and Sleep Stop Working

At some point, things stop adding up the way they used to. You are not doing anything extreme. Meals are fairly balanced, sleep is decent most nights, and you stay active. By most reasonable standards, everything should be fine, yet your body tells a different story. Mornings feel heavier than before, even after a full night in bed. By the middle of the day, energy drops without any clear trigger. Weekends help a little, but

read more

How To Inspect Online Body Jewelry Photos For True Quality When Shopping

Jewelry shopping online must involve attention to detail and in particular, when considering product photos. In contrast to shopping in a brick-and-mortar store, you are not able to touch the product or look at it in other perspectives. Due to this, photographs act as the main source of information regarding the craftsmanship, materials as well as the quality of the piece in general. Knowing about how to read between these images can guide you to

read more
You've loaded all available articles in this category