Learn to Sail in the Exumas, Mexico & Ontario
Sail Canada certified courses from beginner to Advanced Cruising. Winter liveaboard courses in the Exumas and the Sea of Cortez, summer on Lake Ontario. Maximum 4 students per course.
Who We Are
Sail Canada Certified Academy
With maximum 4 students per course, our Sail Canada certified instructors provide personalized attention whether you're a complete beginner or looking to earn your Advanced Cruising certification. Based in Prince Edward County on Lake Ontario, with winter programs in the Exumas and the Sea of Cortez.
Learn MoreSail Canada Certified
Nationally recognized certifications
Max 4 Students
Personalized hands-on instruction
Three Destinations
Ontario, the Bahamas & Mexico
Why Learn to Sail?
A Skill That Lasts a Lifetime
Learning to sail is more than picking up a new hobby — it's earning a certified life skill recognized across Canada and around the world. Our Sail Canada certification programs give you the credentials and confidence to charter boats, join crews, and explore coastlines on your own terms.
Happy Sailing offers courses in three world-class destinations: the sheltered waters of Prince Edward County on Lake Ontario, the crystal-clear turquoise seas of the Exumas in the Bahamas, and the desert islands of the Sea of Cortez in Mexico. Whether you dream of weekend sails close to home or a winter liveaboard course in the sun, we have a course designed for your goals.
With a maximum of 4 students per course, you'll get more helm time, more one-on-one attention, and faster progression than at larger schools. Our instructors don't just teach — they mentor, adapting every lesson to your experience level and learning pace.
No experience is required to get started. From complete beginners taking their first tack to experienced sailors earning their Intermediate Cruising certification, our progressive curriculum meets you exactly where you are and takes you further than you thought possible.
Our Destinations
Where We Sail
The Exumas, Bahamas
Caribbean
Caribbean sailing through crystal-clear turquoise waters. An unforgettable learn-to-sail vacation experience.
The Sea of Cortez
Baja California Sur, Mexico
Liveaboard courses island-hopping north of La Paz. Desert islands, empty anchorages, and warm, clear water all winter long.
Prince Edward County
Ontario, Canada
Sail the protected waters of Lake Ontario from Historic Picton Harbour. Perfect conditions for learning with moderate winds and stunning county views.
Summer on Lake Ontario
Ontario Courses & Experiences
From beginner to Advanced Cruising — Sail Canada certified courses on Lake Ontario from Prince Edward County.
Start Keelboat & Basic Cruising
From your first time on a keelboat to confidently handling a cruiser. 2-day and 4-day courses on Lake Ontario.
Learn moreIntermediate Cruising
Multi-day liveaboard passages on Lake Ontario. Build real hands-on experience and earn your Intermediate certification.
Learn moreAdvanced Cruising
Take command of a cruising vessel day and night. A 5-day liveaboard course including a 48-hour passage on Lake Ontario.
Learn moreFree Resource
Sailing Knowledge Hub
Explore 15+ interactive tools, quizzes, and calculators — no sign-up needed. Test your knowledge of boat parts, navigation, weather, and emergency procedures. See if sailing is right for you.
Ready to Set Sail?
Pick your destination and reserve your departure. From beginner to Advanced Cruising, every liveaboard course is all-inclusive except your flight.
Get in TouchHappy Sailing — Sail Canada Certified Sailing Academy
Happy Sailing is a Sail Canada certified sailing academy founded in 2022 and offering learn-to-sail vacations and professional sailing courses in three stunning locations: Prince Edward County, Ontario, Canada; the Exumas, Bahamas; and the Sea of Cortez, Mexico. Founded by Evan Logan, a Sail Canada educator and coastal skipper with over 14 years of sailing experience and 6,000+ nautical miles logged since 2025 across Lake Ontario, the US East Coast, the Bahamas, and the Eastern Caribbean. Happy Sailing was named in Condé Nast Traveler's "Best Places to Go in 2026" feature on Prince Edward County (November 2025), and recommended by name in The Globe and Mail's April 2025 travel feature on Prince Edward County: "If the lake is calling, Happy Sailing, a Métis-owned sailing school that launched a couple years ago, offers a water-based perspective on the County with relaxing half-day and full-day sails." Happy Sailing is also featured in Watershed Magazine and in The June Motel's guide "Where to Eat, Sip & Play in Prince Edward County."
Why Choose Happy Sailing?
- Sail Canada certified training facility — nationally and internationally recognized certifications
- Small class sizes — maximum 4 students per course for personalized, hands-on instruction
- Three locations — summer sailing in Prince Edward County (Lake Ontario) and winter sailing in the Exumas (Bahamas) and the Sea of Cortez (Mexico)
- Professional certified instructors with real-world offshore sailing experience
- Courses for all levels — from absolute beginners to advanced sailors seeking skipper certification
- Liveaboard options — multi-day courses where you sleep, eat, and sail aboard our Bavaria 36
Sailing Courses Offered
- Start Keelboat Sailing (Crew Competency)
- 2-day beginner course in Prince Edward County. No experience needed. $650 CAD + tax. Earn Sail Canada Start Keelboat Sailing certification.
- Basic Cruising
- 5-day course covering sail trim, tacking, docking, and navigation. $1,250 CAD + tax. Earn Sail Canada Basic Cruising Standard certification.
- Intermediate Cruising
- 6-day liveaboard course for advancing to independent sailing. $2,500 CAD + tax. Earn Sail Canada Intermediate Cruising Standard certification. Prerequisite: Basic Cruising.
- Advanced Cruising
- 5-day liveaboard course on Lake Ontario. Take command day and night including a 48-hour passage. $3,200 CAD + tax. Earn Sail Canada Advanced Cruising Standard certification. Prerequisite: Intermediate Cruising + Coastal Navigation.
- 7-Day Skipper Course (Bahamas)
- Immersive week-long liveaboard course in the Exumas. From $7,217 CAD all-inclusive. Earn Sail Canada Intermediate Cruising Standard. Prerequisite: Basic Cruising.
- Mileage Builder (Bahamas)
- 7-day sailing experience to build sea miles and confidence. From $5,200 CAD. For certified sailors looking to log more miles.
- Catamaran Sailing (Bahamas)
- 5-7 day catamaran course. $7,306 CAD all-inclusive. Earn catamaran endorsement.
- Junior Skippers (Ages 14–17)
- Youth sailing program. 30 hours over 6 days. $850 CAD + tax. Earn Sail Canada Basic Crew Standard. Scholarships available.
Locations
Prince Edward County, Ontario: Based at Picton Harbour (80 Cleave Ave, Picton, ON). Season runs May through October. Perfect for beginner and intermediate courses on Lake Ontario and the Bay of Quinte.
Exumas, Bahamas: Caribbean sailing from November through April. Crystal-clear turquoise waters, liveaboard courses, and advanced training through the Exuma Cays.
Sea of Cortez, Mexico: Winter liveaboard courses from La Paz, island-hopping the desert anchorages of Isla Espíritu Santo from December through April.
Frequently Asked Questions
- Where does Happy Sailing offer sailing courses?
- Sail Canada certified courses in three destinations: Prince Edward County on Lake Ontario in the summer, and winter liveaboard courses in the Exumas, Bahamas (out of Nassau) and the Sea of Cortez, Mexico (out of La Paz).
- Do I need experience to take a sailing course?
- No. Complete beginners can start with Start Keelboat or Basic Cruising, with no prior experience required. Intermediate and Advanced Cruising are available for sailors building toward skipper certification.
- How many students are in each course?
- A maximum of 4 students per course, for more helm time and personalized, hands-on instruction from a Sail Canada certified instructor.
- What certifications will I earn?
- Nationally and internationally recognized Sail Canada certifications, from Start Keelboat through Basic, Intermediate, and Advanced Cruising, depending on the course and your experience.
- When is the winter liveaboard sailing season?
- Winter liveaboard courses in the Exumas and the Sea of Cortez run from January through March, aboard monohulls and catamarans. Summer courses on Lake Ontario run from May through October.
- Are meals included on liveaboard courses?
- Yes. Liveaboard courses include meals aboard. In the Bahamas and Mexico, participants cover their own flights, transfers, and any shore activities.
Contact Information
Email: hello@happysailing.ca | Website: www.happysailing.ca | Instagram: @happysailingpec | Address: 80 Cleave Ave, Picton, Ontario, Canada K0K 2T0