Happy Sailing Academy
Caribbean Sailing School
Learn to Sail in the Exumas, Bahamas
View Pricing & DatesYour Instructor
Welcome Aboard
Hi, I'm Evan -- a Sail Canada educator and coastal skipper. I'm living aboard Sweetwater, a 2011 Bavaria 36, my home and your mobile classroom. In October 2025 I sailed her from Prince Edward County, in Lake Ontario to the Bahamas.
Join us this winter where I will teach you how to not just sail, but to cruise. We cover topics such as sail theory, safety, navigation and how to truly liveaboard!
Are you a new sailor? An adventurer? Are you simply curious and want to spend a week with me experiencing life at sea, exploring islands and meeting new people? If you answered 'Yes', then I want to sail with you. Join me for the adventure of a lifetime.
-Fair Winds
The Full Package
What's Included
Everything you need for an unforgettable week on the water.
Snorkel islands and experience protected marine habitats
Private cabin aboard a modern sailboat
Maximum 4 candidates per course (and a minimum of 2)
Hands-on training from a top Sail Canada instructor flown in for your course
Learning materials and your Sail Canada logbook
Official Sail Canada Basic Cruising & Intermediate Cruising certifications or both
Online zoom sessions pre-departure
All meals aboard (alcohol not included)
Fees (docking, fuel, water, taxes and permits)
Instructor gratuity
Investment
So, you're interested, what's the cost?
When you book the whole boat for up to 4 people.
When you book as a couple sharing a cabin.
Guaranteed private cabin for the ultimate adventure.
No hidden fees! What you see is what you pay. Tax, fees, grats, provisions, certifications and more! All included in this flat rate!
Additional Programs
Schedule
Available Dates
Secure your spot -- courses fill up fast.
January
February
March
April
What Our Students Say
Testimonials
By the end of the course, we had developed solid seamanship skills, a strong understanding of boat systems and life aboard, and improved our navigation and sail planning -- all expertly guided by the instructors.
The perfect blend of fun and education -- I gained so much confidence about chartering and sailing. The instructors handle all the details so you can focus on learning while you enjoy your trip.
Evan's expertise and passion for teaching created an engaging, supportive environment where we felt confident tackling new challenges. His ability to break down complex skills into manageable steps made learning both effective and enjoyable.
My husband and I took our Basic sailing course in the Bahamas just a couple of weeks ago. Evan was very patient, knowledgeable, and professional. We learned so much from him and we would highly recommend taking his course.
Ready to Book Your Adventure?
Fill out the inquiry form or reach out to us directly — we'll help you find the right course and dates.
Get in TouchBookings handled by our travel partner
Catherine Davis
416-566-5264 · TICO 50013277
Prices include tax. A non-refundable deposit of 50% is required to book. All funds in Canadian dollars. You are responsible for your own travel insurance.