Sailing Toronto

The 2 hour sailing experience is a great choice to get introduced into the sailing world aboard our luxurious 41' Beneteau Yacht. This trip requires no prior sailing knowledge or experience. Being part of a small group (max 12 people) you have the option of participating to the extent you want: Take the helm and be "master and commander" of your yacht as you tack and gybe in a circumnavigation of the Toronto Islands. Or sit forward on the deck in a cozy beanbag chair as deck candy or rail meat (as the boat heels over). Whether you are learning and practicing the new sailing skills or sunbathing, while enjoying Toronto skyline and Lake Ontario breeze, your 3hrs will not be long enough.
Every sail is a different experience and your knowledgeable captain and mate will ensure yours is unforgettable. Come aboard and show us your best "king of the world".

The 3 hour sailing experience is a great choice to get introduced into the sailing world aboard our luxurious 41' Beneteau Yacht. This trip requires no prior sailing knowledge or experience. Being part of a small group (max 12 people) you have the option of participating to the extent you want: Take the helm and be "master and commander" of your yacht as you tack and gybe in a circumnavigation of the Toronto Islands. Or sit forward on the deck in a cozy beanbag chair as deck candy or rail meat (as the boat heels over). Whether you are learning and practicing the new sailing skills or sunbathing, while enjoying Toronto skyline and Lake Ontario breeze, your 3hrs will not be long enough.
Every sail is a different experience and your knowledgeable captain and mate will ensure yours is unforgettable. Come aboard and show us your best "king of the world".

We have condensed our highly successful 7hr Learn to Sail in a Day program to highlight the best parts of sailing.
This entry level Sail Canada course is taught on our specially designed First 22. This course is intended to provide novice boaters the opportunity to experience the joys of sailing in a relaxed and safe environment.
Sailors will participate in:
1. Reviewing basic safety when participating as crew.
2. Preparation of boat for departure.
3. Departure from dock as crew.
4. Assist in activities required to sail while underway - including raising and lowering sails, sail trim, helming.
5. Returning to dock as crew.
This 3hr class provides a great opportunity for first time sailors to get out on the water with an experienced instructor . With minimal learning objectives this course can be easily adapted to meet the comfort level of first time boaters or more experienced individuals.











Transport Canada Notice
These training sessions will require short periods of moderate upper body exertion, and a moderate level of arm strength. Participants will have the opportunity to experience sun, wind, spray, rain, and temperatures consistent with the time of year they take part in this activity. When underway the vessel may exhibit irregular motion due to wind and waves and temperatures may be cooler than on land. Participants will be expected to learn and demonstrate skills and perform tasks while the vessel is at the dock, at anchor, and when the vessel is underway. In a day sailing format, vessels will be underway for varying periods of time (up to 8 hours), during daylight, in light to moderate wind and sea conditions. These sessions are suitable for most fitness levels and will provide a good body core workout.

Our most popular Special Event Sail is perfect for “date night”, a group of friends or to make new friends. Each event begins at 6pm as we set sail through the Toronto Island Lagoons and then a circumnavigation of our famous archipelagos providing spectacular city and lake views. Your sail is curated by our in-house sommelier and includes a selected variety of premium wines with specialty cheeses and other surprises to tantalize your taste buds. Of course the evening ends with a decadent tray of sweets.

Celebrate this monthly event with Gone Sailing Adventures. We sail later into the night on these evenings aboard our luxury 41’ yacht, enjoying the evening breeze on Lake Ontario. As the sun sets, we continue our voyage under the bright moonlit sky. Beverages and hors d'ouevres included to toast the full moon each summer month. Each sail carries a special surprise theme based on its name
May 26 Flower
June 24 Strawberry
July 23 Buck
Aug 22 Sturgeon
Sept 20 Harvest

Summer is full of reasons for sailing getaways. Charter your private yacht and invite your family, friends or colleagues to enjoy holidays, long-weekends or retreats organized by the GSA team or plan your own celebration on one of our boats

2014 Beneteau First 22 (max 4 guests)
Hot Flash is the smallest boat in our fleet but a great sail nonetheless. Specifically built with the novice sailor in mind, this boat is stable, yet fast and the foundation of our Learn to Sail Program. Accommodating a maximum 4 students and an instructor, this day sailor has all the controls easily accessible to make learning to sail fun and uncomplicated.

Summer is full of reasons for sailing getaways. Charter your private yacht and invite your family, friends or colleagues to enjoy holidays, long-weekends or retreats organized by the GSA team or plan your own celebration on one of our boats

2014 Catalina 275 Sport (max 5 guests)


This yacht is part of our Small Boat Club and designed for exciting day sailing and crew participation
The handsome Catalina 275 Sport is coupled with a powerful rig with large main and self-tacking jib, which makes the 275 not only fast, but also super-easy to sail. The cockpit is what the 275 is all about. The helmsman will become reacquainted with the simple pleasure of steering a well-balanced responsive boat with a tiller from the comfortable, ergonomically designed outboard sides. With lots of room for up to 5 crew, this is a great boat for a small group who wants to sail. Accommodations below are adequate for weekending or just getting out of the weather, and an enclosed head is always appreciated, even on day sails.

Summer is full of reasons for sailing getaways. Charter your private yacht and invite your family, friends or colleagues to enjoy holidays, long-weekends or retreats organized by the GSA team or plan your own celebration on one of our boats

2014 Beneteau Oceanis 38 (max 8 Guests)

This is the first North American build of the Oceanis 38 and saw its maiden season in Toronto in 2014. This luxury yacht is the a recent development of the French Beneteau yard and has been awarded as the best boat in its category.
The amount of space available both above and below the deck is unique. Accommodating 8 guests, the huge cockpit features dual helms, long seats down either sides and a folding table in the center. Below deck there is a bold modern look.
Our Oceanis 38 "UnPlugged" was custom built for Gone Sailing Adventures to become a perfect fit for private charters, team building, races, etc.
We take care of arranging gourmet catering and beverage service. Boats can be anchored for swimming, sunbathing and barbeque. Take in the Scenic views of the Toronto skyline for you next adventure on your private yacht!

Summer is full of reasons for sailing getaways. Charter your private yacht and invite your family, friends or colleagues to enjoy holidays, long-weekends or retreats organized by the GSA team.





2014 Beneteau Oceanis 41 (max 12 guests)
WhiRLygirl is one of our largest yachts. This Beneteau Oceanis 41 yacht was launched in 2015 and returned to Toronto from sailing the Virgin Islands in 2016. During its maiden season, it along with its crew hosted the Prime Minister of Canada - Justin Trudeau and his family.
This yacht accommodates up to 12 guests. She is incredibly spacious with three double cabins and a classically styled salon. The yacht was designed for luxury entertaining. It makes her a perfect fit for sailing across the lake or private charters. It is a sistership of similar design to Australian Kiss.





We take care of arranging gourmet catering and beverage service. Boats can be anchored for swimming, sunbathing and barbeque. Take in the Scenic views of the Toronto skyline for you next adventure on your private yacht!


Reduced group pricing only available Monday-Thursday (excluding holidays)

3hr minimum on Weekends (Friday-Sunday and Holidays)

Summer is full of reasons for sailing getaways. Charter your private yacht and invite your family, friends or colleagues to enjoy holidays, long-weekends or retreats organized by the GSA team or plan your own celebration on one of our boats


45' Cruisers Yacht(max 12 guests)
This yacht provides a wide open deck and enclosed, exterior seating. The interior includes a large living area for socializing as well. The extra large swim platform provides for more lounging area as well as easy access in and out of the water for those days when you just have to jump in.
This yacht is located at our Polson Pier location, across from the Rebel Night Club. Let her crew host you and show you an amazing time on the water.
This yacht is subject to availability. Once reservation is made it must be confirmed manually by our team. You will be contacted upon receipt of your booking to confirm your reservation.

Start Times are flexible throughout the day and not just as posted on the booking calendar. Please call, chat or email for available start times.

Food and Beverage Policy


All weekend sails are a minimum 3hrs (except 10am or 1030am starts -2hr charter available)

This summer, Gone Sailing Adventures is proud to deliver the newest luxury yacht available for private rental to Toronto. “Decompression” a 2021 42’ Fountain Pajot
catamaran arrives to our dock on June 1.
This beautiful yacht is available for private charter for up to 18 guests. Be the first to experience luxury and bespoke cruising with Gone Sailing Adventures.
Charter price includes Captain and 1 or 2 crew.
This yacht is sold as BYOB and self-catered, Beverage and Catering service are available separately. Weekend Pricing Midweek Pricing
2hr $2399* 2hr $2099
3hr $2899 ** 3hr $2599
4hr $3799 4hr $3499


*weekend morning only
**Min 3hr Charter on Weekend/Holiday