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Happy Sailing.

Sail Canada–certified keelboat courses and skipper training from Picton Harbour in Prince Edward County, with winter liveaboards in the Exumas

01 — About

The brief.

Happy Sailing is a Sail Canada–certified sailing academy based at 80 Cleave Ave on the Picton Harbour boardwalk in Prince Edward County, founded in 2022 by Sail Canada Educator Evan Logan. The Ontario school runs from May through October on Lake Ontario and the Bay of Quinte, with a winter program operating from Nassau through the Exumas island chain from November through April. Courses follow the Sail Canada cruising pathway — Start Keelboat, Basic Cruising, Intermediate, Advanced — and cap at four students per session aboard Sweetwater, a 2011 Bavaria 36. Day-sail experiences and a Junior Skippers program for ages 14–17 sit alongside the certification courses.

02 — Programs

11. ways in.

  1. 01

    Start Keelboat Sailing Standard

    For: Beginners, no prerequisites; max 4 studentsWhen: June 13–14, July 18–19, August 29–30

    A two-day introduction to keelboat handling aboard Sweetwater at Picton Harbour, leading to Sail Canada Start Keelboat Sailing certification. With four students per session, instruction stays hands-on across rigging, points of sail, and basic boat handling — the entry rung of the Sail Canada cruising pathway, with no experience needed to enroll.

    $650 CAD + tax / person

  2. 02

    The Afternoon Sail

    For: Couples and beginners; max 6 guests per tripWhen: May through September

    A three-hour sail out of Historic Picton Harbour aboard a 36-foot cruising sailboat. Guests can take the helm or sit back and watch Prince Edward County's shoreline from the water — a low-commitment first taste of sailing for couples or small groups, with no experience required.

    $100 / person (group of 4); $120 / person regular

  3. 03

    The Half-Day Escape

    For: Up to 6 guestsWhen: May through September

    Five hours along the Prince Edward County coastline with a swim stop at a hidden cove and an optional locally-sourced lunch aboard. Longer than the Afternoon Sail and built around exploration rather than instruction — for groups who want the full sailing-day arc without taking on a certification course.

    $150 / person (group of 4); $175 / person regular

  4. 04

    The Private Day Sail

    For: Groups up to 6 — birthdays, proposals, team outings, celebrationsWhen: May through September

    A full-day private charter aboard Sweetwater with a dedicated skipper. Whole-boat exclusivity for up to six guests, with the day shaped around the group rather than a fixed itinerary — booked for milestones and small celebrations on the Bay of Quinte and Lake Ontario.

    $1,050 for up to 6 people

  5. 05

    Basic Cruising Standard

    For: Beginners, no prerequisites; max 4 studentsWhen: June 5–8, July 3–6, July 10–13, August 21–24

    A four-day day-sailing course combining theory and on-water practical work, leading to Sail Canada Basic Cruising certification. Sessions cover boat handling, navigation fundamentals, and crew roles aboard Sweetwater at Picton Harbour. No prerequisites, four students per session.

    $1,250 CAD + tax / person

  6. 06

    Liveaboard Cruising Program

    For: Sailors pursuing Basic or Intermediate Cruising; max 4 studentsWhen: June 21–26, July 26–31, August 9–14

    A six-day liveaboard course aboard Sweetwater covering Basic or Intermediate Cruising depending on the student's track. Intermediate Cruising candidates need Basic Cruising plus VHF Radio and Basic Coastal Navigation in advance. Includes onboard accommodation and meals across Lake Ontario and the Bay of Quinte.

    $2,500 CAD + tax / person

  7. 07

    Junior Skippers

    For: Ages 14–17

    Six days of instruction over three weeks for ages 14–17, leading to Sail Canada Basic Crew Standard certification. $850 CAD + tax. Session dates published on request — contact the academy for the current Ontario schedule.

    $850 CAD + tax

  8. 08

    Caribbean 7-Day Skipper Course (Exumas)

    For: Sailors with Basic Cruising; min 2, max 4 studentsWhen: November–April; 2026/2027 season launching July 2026 (waitlist)

    A seven-day liveaboard leading to Sail Canada Intermediate Cruising, routing Nassau → Norman's Cay → Warderick Wells → O'Brien's Cay → Staniel Cay → Shroud Cay → Athol Island and back to Nassau. All-inclusive pricing covers taxes, meals, certifications, fuel, docking, and instructor gratuity, with snorkeling at marine habitats along the route. Booking handled by Zebrano Travel.

    From $3,700 CAD / person (group rate); $4,600 couple's; $5,200 single occupancy

  9. 09

    Advanced Cruising Standard

    For: Sailors with Basic & Intermediate Cruising + navigation + VHF; max 4 studentsWhen: July 20–24

    A five-day liveaboard on Sweetwater leading to Sail Canada Advanced Cruising certification. Includes private cabin, meals, instructor, materials, and docking fees. Heavy prerequisites — Sail Canada Basic and Intermediate Cruising, plus navigation courses and VHF radio endorsement — gate enrollment.

    $3,200 CAD + tax / person

  10. 10

    Mileage Builder (Exumas)

    For: Sailors with any cruising certificationWhen: November–April; 2026/2027 dates pending

    Seven-day Exumas voyage aboard Sweetwater for sailors holding any cruising certification, from $3,700 CAD / person all-inclusive. Used to log offshore miles rather than earn a new certification; 2026/2027 dates pending.

    From $3,700 CAD / person (including tax)

  11. 11

    Catamaran Sailing (Exumas)

    For: Sailors with Basic Cruising; minimum 3 students

    Five-to-seven-day catamaran course in the Exumas for sailors with Basic Cruising, minimum three students. Approximately $7,500 CAD / person all-inclusive. Session dates not yet published.

    ~$7,500 CAD / person (including tax)

04 — Visit

Get in
touch.

Visit Happy Sailingarrow_outward
Phone (Caribbean bookings via Zebrano Travel (Catherine Davis))
416-566-5264
Address
80 Cleave Ave, Picton, ON K0K 2T0 (Ontario season May–October); Nassau / the Exumas, Bahamas (November–April)
AER’s guide to Happy Sailing · Compiled from www.happysailing.caLast verified 2026-05-26