Learn To Sail

We firmly believe that sailing can be taught in a single afternoon.

Will you be any good at it? Possibly.

Will you want to do it again? Most likely.

Will you learn something new? Definitely.

Book A Session

Goldenrod is undergoing a refit over winter ‘25/26 where she is getting a new engine, new deck and topside paint, a complete refresh of brightwork, new cushions, and a head installed. Our goal is to make Goldenrod an exact, mini replica of Friend Ship and Wild Rose.

Meet Goldenrod

Our 22’ Friendship Sloop, a mini version of Friend Ship and Wild Rose, is perfect for intimate private charters and our Learn To Sail program. Goldenrod is a tiller-steered keelboat- the best ‘first’ sailboat. She is responsive and stable, giving immediate feedback to the skipper while keeping the occupants comfortable and safe. NO capsizing , just gentle and controlled tacks through the wind.

Book Learn To Sail

Highlights

  • After you’ve passed our sailing certification and our crew feels comfortable in your ability to handle Goldenrod, you are welcome to rent the boat on your own. Take friends, family, and loved ones out on a gorgeous traditional sloop and show off your skills. Starting from 0 experience, it should take 3-4 sessions to receive our certification to take Goldenrod out on your own. If you have experience it could take fewer sessions.

  • Our staff will meet you wherever your skills are at, whether you’d just like a guided refresher to safely shake off the cobwebs, or you’ve never held a tiller in your life. This course is private only, and will be tailored to you.

  • Whistling Man’s Learn To Sail course is designed to fit your schedule. We offer this course by-the-session, if the weather is bad you receive a full refund and will (hopefully) find time to book another course!

  • Being a private-only course, the price is the same whether you book for just yourself or want to bring 1-3 other people. This course is designed for adults, however all ages are welcome!

Book Learn To Sail

The Course

Parts of the Boat

Get to know every major component of Goldenrod- sails, mast, boom, standing and running rigging, tiller, engine controls, cleats, and safety gear. Understanding how each piece works and why it matters will help you move with confidence, communicate clearly, and feel at home on deck from the very first lesson.

Safety

Learn the core principles that keep sailors safe on the water: communication, situational awareness, PFD use, emergency procedures, fire and flood response, and how to avoid common risks. You’ll build habits that make good seamanship second nature, creating a calm, controlled environment for everyone aboard.

Knot Tying & Handling

Get to know the knots every sailor relies on. Cleat hitch, bowline, rolling hitch, figure eight, and more. You’ll learn line safety, coiling, throwing a line, and proper techniques for handling dock lines and running rigging. Solid line handling is the most obvious signs of a competent sailor.

Navigation Basics

Learn the foundations of getting from A to B on the water: aids to navigation, depth awareness, chart reading & plotting, and right-of-way rules. We’ll cover how to interpret your surroundings, stay in safe water, and plot simple courses so you can navigate in unfamiliar territory.

Weather Forecasting

Discover how to read the wind, clouds, waves, and marine forecasts to make smart decisions before and during a sail. We’ll cover local weather patterns on Lake Champlain, how storms develop, and how to interpret wind shifts so you’re always one step ahead of changing conditions on the lake.

Maneuvering Under Engine

Gain full control of the boat under power, especially at slow speeds. Learn throttle control, turning radius, shifting techniques, backing, pivoting, and handling wind or current around docks and tight spaces. This section builds the skills needed to operate the boat smoothly when the sails are down.

Maneuvering Under Sail

Practice tacking, gybing, sail trim, and balancing the boat for smooth, controlled handling. Learn how to adjust power through sheet tension and sail shape, and how to reef the sails when the wind picks up- an essential skill for comfort and safety. Build the timing, feel, and decision making needed to sail with confidence.

Docking

Docking shouldn’t be stressful. You’ll learn how to approach with the right angle and speed, manage momentum, communicate clearly with crew, and secure lines efficiently. We’ll practice real world docking scenarios so you become comfortable landing the boat in wind, current, and busy marinas.

Anchoring & Mooring

Learn how to choose an anchorage, set and retrieve an anchor, and pick up a mooring safely. We’ll cover scope, bottom types, load on the rode, wind shifts, and best practices for securing the boat. This section gives you the confidence to stop and stay anywhere, whether for lunch or overnight.