Sailing Instruction

DMSail offers highly customized and personal learning trips to our clients. We offer basic, intermediate and advanced courses in sailing and navigation. Our week-long, live-aboard cruising format provides the most immersive environment possible and a more thorough experience than being on the boat just a few hours a day.

We limit the number of trips we deliver each year (6 to 8 per calendar year) as our focused is on creating and delivering rich experiences with personalized training.

Our course curriculum is ASA based and follow ASA standards and guidelines.

In additional to ASA focused courses, we also offer experience building trips which are not course specific and instead are focused on further development of skills and knowledge. Get even better at anchoring, mooring, docking, sail trim, sailing distances. weather, costal cruising, blue water cruising and emergency scenarios.

All our adventures include hands on sailing/training as well as opportunities to experience and immerse yourself in the local culture.

Courses

How We Do It

We preschedule and offer set trips that anyone can sign up for.
We also will schedule a trip based on a small group of students interested in learning together. A minimum of three students are required.
Training is delivered in several locations around North America
If you train with us on Vancouver Island or British Virgin Islands (BVI), we use our own boats. Few sailing schools have training boats at this level of comfort, technology and equipment.
For trips outside of Vancouver Island and BVI, we secure the ideal sailboat well suited for brand new and developing students.

American Sailing
Association

The ASA is one of the largest sail instructing organizations in the world with a well-developed sailing curriculum and standards.
The association offers a wide range of sailing courses focused on producing knowledgeable, safe and experienced skippers and crew members for recreational sailing adventures. With ASA certifications you will have the ability to charter boats in locations all around the globe.

ASA Sailing Courses

DMSail delivers the following ASA courses:
101 Basic Keelboat
103 Basic Coastal Cruising
104 Bareboat Cruising
105 Coastal Navigation
106 Advanced Coastal Navigation
114 Cruising Catamaran

To better understand what each course includes and the associated benefits, visit the source of this information at ASA (https://americansailing.com/) as this is where the information is always most current.

Client Testimonials

“DMSail provided personalized instruction that helped me refine existing skills and learn new techniques. After taking the course, I walked away a better sailor with a new perspective on life”

Brady 2024 BVI

"I had a fantastic experience learning to sail with Matt. He knows his stuff inside and out and explains every concept clearly and patiently. Even when I made mistakes, I always felt completely safe—he was calm, composed, and totally in control. Matt’s calm, confident coaching greatly impacted my comfort and progress on the water. I highly recommend him to anyone looking to learn sailing the right way."

Nathan 2024 Antigua

“I was surprised and very happy with the amount of time we practiced all the practical elements that we were learning”

Monica 2025 Vancouver Island

“I could tell my instructor had extensive experience in developing students’ skills and knowledge. I would highly recommend them”

Marcus 2025 Grenada

“Our instructor was extremely competent and did a great job developing my skills and knowledge. He also included some incredible snorkeling experiences and anchoring near beaches that most people will never see in the Sea of Cortez”