Hi, I'm Evan — a Sail Canada educator and coastal skipper with 14 years on the water and four years as a professional coach.
My approach blends technical sailing education with a feel-based, supportive style rooted in my hospitality background. The goal is simple: create a calm, capable learning environment where you build real confidence.
In 2025, I logged over 3,000 nautical miles sailing around Lake Ontario, offshore of the coastal US, the Bahamas, and the Eastern Caribbean including Grenada and St. Vincent and the Grenadines. That experience shapes how I teach. We focus on decision-making in real conditions, small crew dynamics, and skills you will actually use — not theory that stays in a textbook.
Courses are run on a modern, well-equipped vessel with intentionally small class sizes. You will stand watch. You will handle lines. You will make calls. You will leave knowing you can take the helm and think clearly under pressure.
Whether your goal is weekend cruising in Prince Edward County, chartering in the Caribbean, or preparing for your own offshore passage, you will gain practical tools in a structured, supportive setting.
After a season teaching in warmer waters, we are back in Prince Edward County starting May long weekend.
If sailing is on your horizon this year, now is the time to claim your spot.
Scroll on to see what we have to offer and choose your next adventure.
Choose Your Adventure
Learn to Cruise
Our cruising programs are designed for all levels — from novice to advanced. Whether you are looking to become a competent crew member, earn your Intermediate certification, or take command with Advanced Cruising, we will get you to your goals!
Our 2-day introductory course will have you confidently handling a keelboat. This course covers the basics in a focused 2-day format. Our curriculum follows the Sail Canada Instructor guidelines.
June 13–14 2 spots left
July 18–19 2 spots left
August 29–30
The basic cruise is the 4-day deeper dive into day sailing. A 4-day course that covers theory and practical skills to become a competent sailor. If you are looking to develop real confidence on the water, this is for you.
June 5–8 1 spot left
July 3–6 1 spot left
July 10–13
August 21–24
Basic Cruising · Intermediate Cruising
Six days living aboard Sweetwater, navigating the islands and anchorages of eastern Lake Ontario. Your instructor tailors the curriculum to your level — whether you're earning your Basic Cruising Standard or building on it with Intermediate. Same boat, same adventure, same price.
June 21–26 1 spot left
July 26–31
August 9–14
Take command of a cruising vessel day and night. This 5-day liveaboard course develops your ability to skipper in an extensive range of weather conditions, including a continuous passage of 48 hours or more on Lake Ontario.
What You'll Learn
- Skipper a 10–15m vessel day and night within 100 NM of shore
- Sail selection, trim, and heavy weather preparation
- Coastal piloting, navigation watches, and passage planning
- Crew overboard recovery procedures (day and night)
- Mooring and anchoring under sail
- Vessel stability, weather forecasting, and emergency handling
Prerequisites
- Sail Canada Basic Cruising & Intermediate Cruising
- Basic & Intermediate Coastal Navigation (or Coastal Navigation Standard)
- ROC(M) VHF with DSC endorsement
July 20–24
Liveaboard Inclusions
- Private cabin aboard a modern, well-equipped sailboat
- All meals prepared aboard
- Sail Canada certified instructor
- All course materials and official Sail Canada logbook
- Docking, fuel, and water fees
- Max 4 students per course
Your Journey
Eastern Lake Ontario Itinerary
Our itinerary is weather dependent and may be adjusted for safety and conditions. We also visit alternative anchorages such as Big Sandy Bay, Wemp's Bay, Marysville, and Bath depending on the winds for that week. Here is a typical route through Eastern Lake Ontario.
Each day includes sail training, theory sessions, and hands-on learning. You also gain access to online learning modules to help you prepare for your exam.
Picton to Prinyer's Cove
Prinyer's Cove to Little Bluff
Little Bluff to Main Duck Island
Main Duck Island to Kerr Bay
Kerr Bay to Glenn Island
Back to Picton — Disembarkation
Sailing Experiences
Not looking for a course? Our sailing experiences are the perfect way to get on the water — from afternoon sails to private full-day experiences with provisioning add-ons. No experience needed.
Our Instructors
Evan Logan
Sail Canada educator, coastal skipper, and founder of Happy Sailing with 14 years on the water and four years as a professional coach. In 2025, Evan logged over 3,000 nautical miles sailing around Lake Ontario, offshore of the coastal US, the Bahamas, and the Eastern Caribbean including Grenada and St. Vincent and the Grenadines — all aboard his Bavaria 36, Sweetwater. His approach blends technical education with a feel-based, supportive style rooted in his hospitality background — creating a calm, capable learning environment where students build real confidence.
As director, Evan oversees all programming and curriculum across both the Ontario and Caribbean schools. Whether it's a weekend course in Prince Edward County or a week-long liveaboard in the Bahamas, he's committed to making every student's experience exceptional.
Evan teaches:
- Sail Canada Introduction to Sailing
- Start Keelboat Sailing
- Basic Cruising
- Intermediate Cruising
- Advanced Cruising
Ken Bourne
Sail Canada instructor and catamaran endorsed skipper. Ken grew up in Atlantic Canada where he developed a lifelong passion for the ocean. With thousands of nautical miles of coastal, offshore, and Caribbean cruising logged across monohulls and catamarans, he brings deep real-world experience to every lesson. In 2019 he sailed his own cruising sailboat from Lake Ontario to the Bahamas. Ken brings patience, enthusiasm, and a genuine love of teaching to the water.
Ken teaches:
- Sail Canada Basic Cruising, Intermediate Cruising and Competent Crew/Helmsman
- ASA 101 – Basic Keelboat, 103 – Basic Coastal Cruising
- 104 – Bareboat Cruising and 114 Cruising Catamaran
Testimonials
Amazing experience! I took the Start Keelboat course with Evan and could not believe how much I learned. Evan was always patient and made sure we were learning and were comfortable. I would highly recommend this course at Happy Sailing even if you have never been on a boat before.
Had such a fun and informative day trip led by Evan who was co-captain on the boat! Such a great instructor. I can't wait to continue my sailing journey with Happy Sailing.
Had a 5 hour sail with Evan today and it was fantastic. He indulged us with all of our questions and took the time to explain the workings of his sailboat. Evan was very attentive and responsive to our needs. Would highly recommend Happy Sailing to anyone out there that wants to get some hands on experience or just enjoy the allure of sailing.
Had such a fun + informative day led by Evan who also cooked us the best lunch. I can't wait to continue my sailing journey with Happy Sailing!
Fantastic experience! Evan is a great teacher and personalizes the experience based on how much you want to learn about sailing versus just cruising around. I learned a lot, the lunch was absolutely delicious and we had fun swimming too.
Getting out on the water with Evan ignited my passion for sailing! The experience is tailored for how much you want to learn. The lunch provided was also very tasty and makes for a great date idea.