So You Want To Go Sailing?
- Sean Duclay
- Sep 2
- 5 min read
Sailing with SailAhead isn’t about experience or fancy gear — it’s about getting on the water, feeling the wind, and being part of a crew. Whether you’ve sailed before or never set foot on a boat, you’re welcome here.
How to prepare: It’s simple — just check the weather before you head out.
☀️ Sunny: hat, sunglasses, light clothes, sunscreen.
🌬️ Cool or rainy: jacket, warm layers, maybe a rain shell.
👟 Shoes: sneakers or anything with grip (no flip-flops).
We’ll provide the boat, the safety gear, and the team. You just bring yourself, and a good attitude!
Ready to get on the water? We’ll guide you—just bring yourself.
Add your email on the next page and keep an eye on
your inbox for upcoming sails and race crew spots.
From there, sailing is about connection — to the wind, the water, and each other. Before you know it, you’ll be trimming sails, steering, and even racing against other crews.
A Brief History of Sailing
Humans have relied on the wind for thousands of years. Ancient Egyptians were already sailing the Nile on reed boats over 5,000 years ago, and by the time of the Phoenicians and Greeks, sailing vessels were crossing the Mediterranean for trade, warfare, and exploration. Over the centuries, sailing carried explorers across oceans, built global trade routes, and even decided the outcomes of wars.
But ships didn’t only carry treasures and explorers. For centuries, millions of men, women, and children were forced across oceans as enslaved cargo — the transatlantic slave trade alone transported over 12 million Africans to the Americas. Sailing was both a tool of connection and a weapon of exploitation, leaving a legacy of both triumph and tragedy.
Today, sailing is less about survival and more about connection — to nature, to the sea, and to each other. It offers a unique blend of tradition and adventure that few activities can match. At the same time, it remains one of the most demanding sports, and in modern times has become a spectacle not unlike Formula 1 — see our SailGP post and the story of when we rented our RIB to SailGP.
For centuries, sailing was also the engine of globalization. Long before steamships and airplanes, wind-powered vessels carried goods, ideas, and people across the world. Entire civilizations rose and fell on their ability to master the sea.
Whaling - Long Island's Forgotten History
In the 18th and 19th centuries, Long Island’s coastline fueled one of the world’s most vital industries: whaling. Sag Harbor and Cold Spring Harbor weren’t just ports — they were global players.
From 1760 to 1850, Sag Harbor rivaled New York City in its volume of square‑rigged ships. President Washington even designated it a Port of Entry, just one day before New York City secured the same status
At its peak in 1844, Sag Harbor boasted a fleet of 63 whaling vessels and a population of 3,621 — a level of maritime activity few towns could match
On the North Shore, Cold Spring Harbor was home to the Cold Spring Harbor Whaling Company, founded by the Jones brothers. Between 1836 and 1862, the company launched nine ships and completed 44 voyages, leaving a lasting industrial and cultural legacy
The scale of Long Island’s whaling industry was massive. In 1847 alone, the region produced 672,971 barrels of whale oil, used across the Western world for lighting and industry
The whale oil is gone, the ships are gone, but the story isn’t. Walk the streets of Sag Harbor or Cold Spring and you can still feel the echoes of that industry in the old captains’ houses, the shipyards, and the sea itself. Whaling was brutal, but it put Long Island on the map and tied it to the engines of the modern world.
Manilla Galleons
For 250 years, massive Spanish galleons crossed the Pacific between Manila and Acapulco—loaded with silk, spices, and porcelain—while silver flowed back east—forming one of history’s earliest global trade networks.
Venetian Merchants
Venice wasn’t built by armies—it was powered by trade. Its Republic’s wealth came from controlling Mediterranean routes and shipbuilding in the Arsenal, one of the earliest industrial complexes, churning out vessels at massive scale.
Zheng Yi Sao
the most successful pirate you’ve never heard of. In the early 1800s, she commanded the Red Flag Fleet, with estimates of 600 ships and up to 40,000 men under her control — making her more powerful than many navies of the time. She defied empires, defeated Chinese and European fleets, and negotiated her retirement on her own terms.
Ship of the line
In the Age of Sail, these floating fortresses were the backbone of naval power. Built to exchange broadsides in line-of-battle formations, ships of the line—often bristling with 74 to 130 cannons and manned by crews of 600–800—defined naval dominance across Europe.
The Basics: How Sailing Works
At its core, sailing is about working with the wind instead of fighting it. A few principles:
Wind as the engine: The sail acts like a wing, creating lift that pulls the boat forward.
Points of sail: Depending on wind direction, sailors adjust their course — sailing “upwind” (zig-zagging in tacks), “downwind” (with the wind behind you), or “across the wind.”
Trim and balance: Small changes in sail angle and crew position make the boat faster, smoother, and safer.
Teamwork: Even simple maneuvers like tacking (turning through the wind) are smoother when the crew communicates.
No experience is required to get started — most new sailors are surprised by how quickly they can learn the ropes with a little guidance.
The Shields: A Classic American Sailboat
The Shields Class was designed in 1963 by naval architect Olin Stephens, one of the most respected yacht designers of the 20th century.
The goal was to create a one-design keelboat — meaning every Shields is built to the exact same specifications, so competition comes down to skill, not equipment.
A few things that make the Shields special:
Length: 30 feet, with a sleek, graceful hull.
Crew: Typically sailed by 2–5 people, perfect for both casual sails and competitive racing.
Stability: With its deep keel, the Shields is safe and steady — great for new sailors and veterans alike.
Active racing fleet: To this day, Shields are raced in fleets across the U.S., keeping the design alive and competitive.
For SailAhead, the Shields is a natural fit: big enough to carry a crew of veterans, responsive enough to be exciting, and simple enough that anyone can learn the basics on their very first outing.
Add your email on the next page and keep an eye on
your inbox for upcoming sails and race crew spots.
Conclusion: From History to Your First Sail
For thousands of years, sailing has carried humanity across rivers, seas, and oceans — building empires, fueling industries, and shaping the world we live in. On Long Island, it left its mark through whaling, trade, and a culture tied to the water.
But sailing isn’t just history. Today, it’s something you can experience directly — the steady power of the wind, the teamwork of a crew, the thrill of steering a classic boat like a pirate captain of old.
Whether you’re a veteran looking for a new way to connect, or simply curious about the sea, stepping aboard is a chance to become part of that long tradition. The water is waiting.
