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, and we're doing it all over again! I will sail another 1,800 nautical miles to reach our winter base.
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
Why This Destination
Paradise on the Edge of the Atlantic
The Exuma Cays are a chain of about 365 islands running 120 miles southeast from Nassau. You sail the chain aboard a monohull or catamaran with a Sail Canada instructor and no more than four students.
The geography creates two distinct sailing environments. The Great Bahama Bank to the west is a shallow sand shelf — 10 to 20 feet of water for hours at a time. Exuma Sound to the east drops to thousands of feet within a mile of shore. The cuts between the cays connect the two.
Winter temperatures average 24°C to 27°C. Northeast trade winds run 10 to 20 knots. Cold fronts pass through roughly weekly, shifting the wind direction and putting your new skills to the test.
The Exuma Cays Land and Sea Park
The middle 22 miles of the chain is a marine protected area established in 1958 — the first of its kind in the world. Nothing is removed from the water inside the boundary. At Warderick Wells, boats use park moorings rather than anchoring to protect the seabed.
Daily Structure
The first day out of Nassau is the longest run of the week. After that, most legs are under 20 miles. You sail every day and anchor every night, completing the full cycle of a cruising day six times over the course of the week.
The Cuts
The passes between the cays carry tidal current twice a day as the Bank drains into and fills from the Sound. Transiting at the wrong time means working against the current and against ocean swell. You plan passages around the tide, not the clock.
Provisioning
Several cays have Bahamian settlements with fuel, supplies, and restaurants. Others are undeveloped. The boat is provisioned in Nassau for the week.
Certification
You earn Sail Canada Basic Cruising, Intermediate Cruising, or both. Both standards are recognized internationally and are what you need to take a boat out on your own, anywhere in the world.
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?
Jan 9, 16 & 23, 2027 departures
Dufour 390 GL or Sun Odyssey 410. The classic Sail Canada training platform, with a direct feel for sail trim and heel. The rate varies by departure week.
Jan 9 & 16, 2027 departures
Lagoon 40. Twin hulls, a level ride at anchor, and considerably more living and deck space for the week.
Feb 5 & 19, 2027 departures
Build sea miles with Evan aboard Sweetwater, his 2011 Bavaria 36 and the boat he sailed from Lake Ontario to the Bahamas. She is his home for the winter season.
Every figure above is a total price per person in Canadian dollars, with taxes, fees, provisions and all meals aboard, gratuities and your Sail Canada certification already included. Your flight is not included. Rates apply to the 2027 departures listed on each card and vary by week and by vessel. Contact us for a final quote for your dates.
Winter Season
Dates & Pricing
Choose a boat and a departure to see your all-in price per person.
Exumas Liveaboard
Sail Canada Basic or Intermediate Cruising, out of Nassau.
Sail southeast from Nassau into the Exuma Cays with a Sail Canada instructor and never more than three other students, anchoring every night and covering the whole cycle of a cruising day.
Every rate is the total price per person in Canadian dollars, with taxes, fees, fuel, all provisions and meals aboard, gratuities and your certification already included. Your flight is not included.
Your Week at Sea
7-Day Itinerary
Nassau to the Exuma Cays and back — island hopping through some of the most beautiful waters on earth.
Our itinerary is weather-dependent and may be adjusted for safety and conditions. Here is a typical route through the Exumas.
Nassau to Norman's Cay
Norman's Cay to Warderick Wells
Warderick Wells to O'Brien's Cay
O'Brien's Cay to Staniel Cay
Staniel Cay to Shroud Cay
Shroud Cay to Athol Island
Nassau — Disembarkation
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.
Student Resources
Prepare for Your 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.