FOUNDER

Sailing since 2005

Drew is an experienced sailor with a long history of training in the Caribbean and beyond, having sailed in over 15 countries with co-founder Matt. His early years on the water fostered a deep respect for the ocean and a strong commitment to helping others build their confidence and capabilities. With a calm, supportive teaching style, he guides students through real-world conditions and develops practical, dependable seamanship.

FOUNDER

Sailing since 2005

Matthew brings a background in aviation instruction to his work on the water, having trained and examined more than 125 pilot candidates before shifting his focus to sailing. His analytical approach, structured teaching style, and extensive sailing experience across multiple regions help students build competence through clear guidance and hands-on practice. His goal is to make learning organized, safe, and confidence-building.

INSTRUCTOR

Sailing since 2010

Eric Penn took a deep dive into sailing in 2010, starting with a World Cruising Club offshore seminar and later coming full circle by crewing a 56-foot monohull from Virginia to the BVI in the Carib 1500 with his friend Captain Matthew Hillhouse. A trial lawyer by trade and teacher by instinct, he loves passing on the skills and judgment needed to cross oceans safely, and finds that instructing keeps his own seamanship sharp. For the past decade he has kept a boat in the British Virgin Islands, where steady trade winds, warm water, and a chain of diverse islands make it his favourite place to sail.

Your instructors are professional captains and ASA-certified educators with thousands of miles and two decades of experience under their keel. They teach you not only how to handle a boat, but how to read a forecast, assess risk, and make the call to slow down, turn back, or stay put when conditions demand it.

Both Captains are certified in:

ASA 101 Keelboat Sailing, 103 Coastal Cruising, 104 Bareboat Cruising, 105 Coastal Navigation, 106 Advanced Coastal Cruising, 107 Celestial Navigation, 108 Offshore Passagemaking, 114 Cruising Catamarans, 117 Celestial Endorsement, Instructor rating for  201 Keelboat Sailing, 203 Coastal Cruising, 204 Bareboat Cruising, 205 Coastal Navigation, 206 Advanced Coastal Cruising, and 214 Cruising Catamarans.

Our training boats are maintained to exceptional standards and inspected regularly, and for overseas voyages we charter only modern, top-of-the-line vessels from trusted fleets that meet or exceed those same safety and equipment standards. Before we ever leave the dock, you will walk through the vessel’s safety gear, learn where everything is stowed, and practise how to use it: PFDs, radios, harnesses, jacklines, fire extinguishers, and more, so you know exactly what to reach for when it matters.

Weather is the living puzzle of every voyage. From your first introductory ASA courses, we slow down and show you how we read forecasts, watch the sky and sea state, and talk through real go or no-go decisions.

In ASA 104 and our more advanced cruising courses, that grows into full passage and contingency planning: weighing wind shifts against tide, choosing safe bail-out options, deciding when to reef early or stay in harbour, and what to do when the forecast does not play out.

We favour learning and safety over “sending it,” and we explain every choice in real time so you leave with a clear, repeatable way to make sound weather decisions on your own voyages.

A strong safety culture depends on every voice, and small groups make sure yours is always heard. From day one, your instructor knows everyone by name, watches how you move on deck, and has the time to check in, correct, and coach until the skills feel natural.

You are encouraged to ask questions, call out concerns, and say if something does not feel right. There is no bravado here. We would rather reef too early, slow down, or repeat a manoeuvre until the whole crew is competent and comfortable than push past anyone’s limits. That personalized time and attention to detail are what keep everyone safe.

Prepared for “what if” so you can focus on “what’s next.”

Throughout your course, you will run over realistic scenarios: a fouled prop in a crowded channel, a failed tack in tight quarters, a dragging anchor in the middle of the night, even a crew overboard or sudden weather shift. Then we slow everything down and walk through what happened, what worked, and what you would do differently next time.

That habit of calm analysis runs through everything we teach. It is taken even further in ASA 104 Bareboat Cruising, where safety checks, emergency procedures, and sound judgment under pressure are cemented as core skills.  By normalizing this kind of debrief, we show you that good sailors are always learning, never guessing.