Breaking water painted in oil — a detail from the author's own work

VOL I · CH I · APR–DEC 2026

The Sailmaker

Wind, spray & cloth. An exploration of the art of sailing and the craft that makes it possible.

Oil on panel · detail

Bearing I

Bearing

Sailmaker

Season

Phase I — Launch

Tide

—

Welcome

Drawn to the salt, spray, canvas and wind, the Sailmaker endures the elements. Stitch by stitch, the yards of canvas and cord come together and draw us to the sea, across the globe, and to one another. The sail carried humanity into civilization, and to this day it continues to inspire adventure, calm, creativity and connection.

This Bearing explores both the craft of the sail and the skill required to harness it. Begin with the basics; as you delve deeper, so will the content.

A sailor is an artist whose medium is the wind.
— Webb Chiles

A Letter from the First Hand

Break the seal — the letter opens below

Introduction letterfolio · i

Welcome to the Sailmaker

i

Written at Beverly, Massachusetts · July 2026

Hello and welcome to the bearing the Sailmaker. The Sailmaker not only cuts and sews the sail, but they harness the wind. Explore the craft of the canvas and how to use it. Like every bearing in Glaukas this is a deep dive into the world of the sailmaker. The material will start shallow introducing you to the basics of sailing and sailmaking, but as you delve deeper into the bearing the depth of the content will grow.

From the Codex — the five motions

01The Calm
Preparation. The loft, the kit, the measured cloth, and the hand setting itself before the first stitch.
02Endurance
Long seams, repeated pulls, and the patient work of keeping canvas serviceable.
03The Breath
The instant the sail fills and craft becomes motion instead of theory.
04The Mend
Reflection. Mending, note-taking, and the calm after strain when lessons can be kept.
05Inspiration
The return to harbor and the desire to share what the year of practice made visible.

Inspiration returns to the Calm. The next bearing begins where this one leaves off, which is why a season closes rather than ends.

I am certainly not an expert on the subject of sailing, sailmaking and the skills involved. I would be described as novice at best, but, I am aspirant to achieve a level of expertise. I did not grow up close to the sea, but rather in Rochester, NY, several hundred miles away from the closest beach. Every year or so my family would go to some New England town. I would get out of the car, run to the beach or dock. There is nothing like that first whiff of salty air when you are away and craving the sea. The smell of the tide. I would stare at the boats out on the horizon, and think about all the possibilities it had to offer.

Though I did not have regular access to a boat in my youth, I do not enter this journey completely ignorant. I first sailed a boat at a summer camp in my early teens. I can still feel the exhilaration of the wind picking up my sail and pushing me up that Finger Lake. The lessons from the Sunfish are broken fragments adding the board keel and portable rudder, hoisting the mast and pulling the sail, when to trim and taking a hit on an unexpected tack. Each fragment comes into my brain unassured and unapplied.

My other more foundational experience was several years later, the first summer back from college. To this day I am not sure how but several high school friends and I convinced some poor fellow to rent us a 23ft sloop out of Kingston, ON in the Thousand Islands. We sailed her up the rather perilous St. Lawrence seaway. My friend, now a naval architect skippered us through the rocks, and currents only running us aground on two occasions. Me and my other friends took up the crew, trimming the sail and tacking. We navigated without wayfinders or GPS using charts and our eyes. My friends and I taking turns leaning over the bow on the lookout for rocks. We slept on secluded island campsites paddling the dinghy into their shores from our found harbors. All of us on the threshold of adulthood playing pirates one final time.

This is my foundation. I am now a man in my 30s with two kids and a full-time finance job. My passion has brought me to the sea and I am now fortunate enough to smell that sea air on a daily basis. There is still something missing though and that is the breath of that wind and that pull on a sail. I have not achieved the goals of that little boy on the dock but I am eager to try. This site is likely not for an experienced sailor but for someone like me without the conventional pipeline of generational knowledge passed down to them, or the means or time required to take lessons, or buy a boat, but an incessant pull towards the water. As I learn more and share my experiences I will incorporate them here and hopefully the end result will be a rich experience leaving you ready to take up the tiller.

—Zach

Lat42° 33′ NLong70° 52′ WBeverly, MA

Pen-and-ink drawing of a small boat under a single sail, one sailor at the tiller on open water — Sailmaker 1
Pen & ink (edited in Adobe InDesign)

GuideReference

A beginner’s reference to sailing

Harnessing the power of wind and water is a complex art. There is a distinct language to the craft, one built on thousands of years of maritime tradition. Click the guide to build your literacy within the world of the Sailmaker.

Your first sail

01
Read the wind and sky first. Rig the boat pointing head-to-wind so the sails cannot fill early.
02
Buoyancy aid on. Know where the mainsheet, tiller, and centerboard are before you leave the dock.
03
Push off and bear away onto a beam reach — the most forgiving point of sail.
04
Steer small and smooth. Push the tiller toward the trouble to turn away from it.
05
When in doubt, let it out: ease the mainsheet until the sail just stops flapping.
06
To turn around, tack: “ready about” … “lee-oh”, and change sides as the bow passes through the wind.

First words aboard

A small vocabulary carries most of a first day on the water.

Port · starboard: Left · right as you face the bow. Port is red, starboard is green.
Bow · stern: The front · the back of the boat.
Windward · leeward: The side the wind hits · the sheltered side away from the wind.
Tack: To turn the bow through the wind so it crosses to the other side. Also: the side the wind is on — port or starboard tack.
Gybe: To turn the stern through the wind — faster and rougher than a tack. Control the boom.
Luff up · bear away: Steer toward the wind · steer away from it.
Halyard · sheet: The line that hoists a sail · the line that trims its angle to the wind.
Heel: The boat leaning under the press of wind. Sit to windward to balance it.
Points of sail: Where you point relative to the wind — close-hauled, close reach, beam reach, broad reach, running — and it decides how you trim. Fig. V
In irons: Head to wind, where the sail cannot fill and gives no drive. Bear away until it fills. Fig. V

On land, we forge, make, and mend. Once the tide takes us, only skill remains.

The whole guide, on its own page →Reference — close it and the drawings begin

Marblehead Dinghies — three dinghies sailing past the iron light tower on Marblehead Neck at sunset, an original oil painting — PL. 01
Marblehead Dinghies
Oil on canvas
Closed — click to open

With the wind astern the sail is a bag. Air enters, the cloth stops it, and the boat is pushed forward at a speed less than the wind. Bring the sail across the wind and it becomes a curved wing: the air bends around it rather than piling into it, and it pulls.

Wind astern 180°Beam reach 90°

Angle 180° · Pull ×1.0

Downwind the sail is a bag. Across the wind it is a wing, and a wing pulls harder than a push.

PlateInteractive

Plate I · The Lug Daysailer, Rigged

Even a small lug (a traditional sailboat with a four-cornered lug sail) is a mechanism of many moving parts. Learning these components is fundamental to understanding how to sail. Hover over any one to name it; click for the full note and what it is made fast to.

Open the plate full-screen →

The mainsheet controls how the sail meets the wind. Let it out too far and the sail shakes: that is luffing. Pull in until it stops and you will feel the boat push forward. Pull further and she stalls — the sail is full but the flow over it has broken. Watch the wake, not the cloth.

Sheet easedSpeed ▮

Ease until it shakes, then pull until it stops. That is trim, and that is most of it.

On the bench in this figure — the blocks a sheet runs through

ArtifactsOne of one

Two blocks, the same problem

Everything the plate above names in outline, somebody once had to make out of wood and iron. These two came off boats and through a bench — the Merriman Bros. block, and one nobody signed. Pick one up and what is known about it is set down beneath, including the one whose honest answer is that nothing is known at all.

Two things on the bench. Pick one up.

The rudder swings opposite your hand and deflects water sideways, and that push on the stern rotates the boat about a point near the centreboard, well forward of where you sit. You are behind the pivot, so your hand and the bow always go opposite ways.

Tiller centred

Push the tiller toward the trouble. The bow goes the other way.

Drawing the plate…

Remarks on The Secret of the Sea

By Henry Wadsworth LongfellowFrom The Seaside and the Fireside, 1850

Ah! what pleasant visions haunt meAs I gaze upon the sea!All the old romantic legends,All my dreams, come back to me.

Sails of silk and ropes of sandal,Such as gleam in ancient lore;And the singing of the sailors,And the answer from the shore!

Most of all, the Spanish balladHaunts me oft, and tarries long,Of the noble Count ArnaldosAnd the sailor’s mystic song.

Like the long waves on a sea-beach,Where the sand as silver shines,With a soft, monotonous cadence,Flow its unrhymed lyric lines;—

Telling how the Count Arnaldos,With his hawk upon his hand,Saw a fair and stately galley,Steering onward to the land;—

How he heard the ancient helmsmanChant a song so wild and clear,That the sailing sea-bird slowlyPoised upon the mast to hear,

Till his soul was full of longing,And he cried, with impulse strong,—“Helmsman! for the love of heaven,Teach me, too, that wondrous song!”

“Wouldst thou,”—so the helmsman answered,“Learn the secret of the sea?Only those who brave its dangersComprehend its mystery!”

In each sail that skims the horizon,In each landward-blowing breeze,I behold that stately galley,Hear those mournful melodies;

Till my soul is full of longingFor the secret of the sea,And the heart of the great oceanSends a thrilling pulse through me.

When the wind blows a leaf, the leaf goes that way. A sail does not: the pull it makes is mostly sideways. The centreboard keeps the boat moving forward and stops her drifting off with the wind.

Slip 34° off her heading

She never stops slipping entirely. A well-sailed board boat gives away a few degrees, always, and a good helm sails as though it were not there.

Three things answer the wind: the sheet, the tiller, and you. When she leans you can let the sail out, come up towards the wind, or move your weight — usually a little of all three. Heel is not only uncomfortable, it is slow. A leaning sail shows less of itself to the wind, and the hull gives away more sideways for every foot it goes forward.

LightToo much

Heel 0° · Crew centreline

Some heel is normal and even fast. Beginners over-correct in both directions — first by hanging on, then by sitting back down too soon.

She will not go straight at the wind, and she will not turn on a sixpence. Everything in this stack follows from those two facts: how to get her bow across the wind, how to get her stern across it, what happens when the turn fails, and how to stop.

Movement oneThe morning calm

Three turns on flat water, which is where you learn them. What none of them answers is the question the day actually poses: the mark is upwind, and no amount of turning gets you there unless the turns add up to something.

Movement twoThe long beat out

A standing lug daysailer under sail, one hand at the tiller

Feature 02 · Interactive

The Helm

The boat of Plate I, on a piece of water that means what it says — real wind, real stream, real soundings, and a crew that answers when called. No score. The sea does not keep one.

Take the tiller

Plate IStanding Lug Daysailer

The mark is astern and the light is going. What remains is the part every beginner dreads and every sailor does a thousand times: stopping a thing that has no brake, beside something solid, once.

Movement threeComing in, late light

Glencoe — an original oil landscape painting by Zach Barkin — PL. 04
Glencoe
Oil on canvas · print from the original
Closed — click to open

PlatePassage chart

Plate II · The Passage, Planned

The water this bearing has been on, and the next passage across it. Wind as it blows now and for three days out, drawn where it blows. Lay down a course and the tacks are worked for the wind that will be there when you reach each leg. Turn on the shore and the chart marks the harbour, the chandlery, the sailmaker’s loft and the pub at the top of the dinghy dock. A chart is a plan and not a promise — read the tide and the seamarks for what the planner cannot see.

Unrolling the chart…

Cutter — a white-hulled gaff cutter under full sail, crew on deck, passing a low shore of trees and rock under a grey-green sky, her sails reflected in the green water; an original watercolor by Zach Barkin — CutterWatercolor on paper11 × 14 in

PL. 06

Close enough to the shore to name it, and too busy with the sails to look.

A new sail is a rare event.
A mended one is Tuesday.

From other hands

FromNantucket Current

Nor’Easter Uncovers Shipwreck On Nantucket’s South Shore

Our note

What the sea does to a hull nobody is mending. The timbers a nor’easter laid bare on the south shore are thought to be the Warren Sawyer’s, wrecked on that beach in December 1884 and buried in its sand since — one storm took her, and another has given a piece of her back.

Read it at nantucketcurrent.com (opens in a new tab)

Every reading on the bearing →

01
Lay & mark
The two cloths overlap by the width of the seam — a hand's breadth, marked once with the rubber's edge. Selvedge to selvedge, no guesswork.
02
Crease
Run the seam rubber the length of the fold until it lies flat and stays there. The cloth should hold the crease without being held.
03
Dress the twine
Draw the flax through the beeswax, three passes. It goes in dry and comes out stiff enough to steer.
04
Stitch
Needle up through both cloths, back down a needle's width along. Even spacing matters more than tightness — a tight seam puckers and the pucker is where it tears.
05
Rub down
Work the rubber back along the finished seam. Whip the ends. The seam is done when it disappears into the sail.

Plate

PL. 03

Medium

Oil on panel · print from the original

Size

Print · 8 × 8 in

Made

Beverly, MA

Crane Beach, Cloud — an original oil painting by Zach Barkin

The weather did the composition; the hand only kept up.

Crane Beach, Blue — an original oil painting by Zach Barkin — PL. 02
Crane Beach — Blue
Oil on wood panel · print from the original
Closed — a deadlight. Nothing to see until you open it

PL. 05 · Schooner

What makes her a schooner?

Two masts or more, every sail set fore and aft, and a foremast no taller than the mast behind it. That last is what separates her from a ketch, which carries its taller mast forward.

Here the foremast is the one nearer the bowsprit, and the mainmast behind it stands higher. The rungs up the shrouds are ratlines, for climbing aloft.

The instant the sail fills and craft becomes motion instead of theory.

From other hands

FromSaltWire

An American schooner in Lunenburg, put up for sale on Facebook Marketplace

Our note

The Sailmaker’s schooner is drawn, and will never need a buyer. This one is real, lying in Lunenburg — the harbour that built the Bluenose — and somebody has to take on her upkeep, or she goes the way wooden schooners go.

Read it at saltwire.com (opens in a new tab)

Every reading on the bearing →

A schooner heeling under working sail in Boston Harbor

Textures of the Tall Ships

Read them seam by seam →

282

Remarks on the calm after a long passage

The sail remembers every wind it has caught. Each thread bears the tension of storms weathered and calms endured. The sailmaker does not create first; the sailmaker listens, and the canvas answers.

Lat 42° 31′ NLong 70° 53′ WBar 29.9— Logbook, Sailmaker bearing

See them in Mercantile Port

The passage

A bearing is a season, not a sitting. What you cut, trimmed, and undid between the first depth and this one is the part worth keeping — and it is the part that disappears first.

Arctelia holds the whole descent as one passage: an orbit for the bearing, an entry each time you came back, and the open questions carried between them. Free while you keep the record yourself; a studio account adds guidance that has read the passage, a preparation canvas, and the tide and wind of every session you logged.

White line drawing on black: four hulls at anchor, masts and yards against an open sea — Plate IV · The Hull at Sea · ink on black

The Sailmaker