Gone Sailing Adventures operates a fleet of modern sailing yachts, each crewed by a Transport Canada licensed captain. For corporate groups, we distribute your team across boats of 8–12 people each — small enough for real conversation, large enough to cover your whole group — and bring the fleet together on the water so the full team reunites before heading back to dock.
This is what separates a corporate sailing charter from everything else on the Toronto waterfront. It’s private. It’s active. Your team is actually involved — taking the helm, reading the wind, navigating past the Toronto Islands toward Tommy Thompson Park. And the city skyline you’ve all seen a thousand times looks completely different from the water.
For groups that want more structure, our 3–4-hour team challenge format turns the outing into a fleet-wide competition: a poker run with on-water challenges including knot-tying, phonetic alphabet drills, and historic flag communication between boats. For groups that want a more relaxed outing, the 2–3-hour social sail gives everyone the chance to take the wheel in a low-pressure, genuinely memorable setting.
Your group arrives at 415 Queens Quay West on the Toronto waterfront. We handle the welcome aboard, the safety briefing, and every logistical detail. You show up — we take care of the rest.
Your Transport Canada licensed captain takes the helm as your group heads out past the Toronto Islands. No other companies. No public passengers. Just your team, the open water, and a setting that makes conversation happen naturally.
The best corporate sailing charters end with your team still on the dock, not wanting to leave. That's what we're building every time we cast off.
Toronto has no shortage of boat-based corporate event options. The large cruise operators — vessels built for 50 to 500 people — dominate the top of search results, but they’re not the right fit for a team of 10 or 30. When your group is one of three companies on board, you don’t get a team outing. You get a table at a floating restaurant.
Gone Sailing Adventures sits in a completely different category. We work exclusively with private groups of <10 to 40+, which means the entire experience — the route, the pace, the format, the conversation — is built around your team. Our sailing yachts have more open deck space than many motor vessels of the same capacity, which means your group can spread out, move around, and actually interact rather than sitting in assigned seats.
We’re fully licensed by Transport Canada and the Alcohol & Gaming Commission of Ontario. We carry a comprehensive risk management program that has satisfied the corporate safety review requirements of major clients including Shell Oil — the same executive risk documentation that shows exactly what our risks are and exactly how we mitigate them. If you need that documentation to get internal approval, we can provide it.
There’s a reason Gone Sailing Adventures has repeat bookings from Toronto’s corporate sector. Engineering firms, financial services companies, legal teams, sales organizations, and technology companies have all brought their groups aboard — and the reason they come back is the same thing every time: it works.
Sailing on Lake Ontario is a genuine first-time experience for most people. In any given corporate group, you might have one person who’s sailed before. That means the VP and the junior analyst are figuring out the same thing at the same time, alongside each other, in a setting where nobody can retreat to their usual role. The barriers that exist in the office simply don’t exist on the water.
What makes our charters specifically effective for corporate groups is the combination of novelty, physical engagement, and the educational layer Howie and his captains weave in naturally — the history of Toronto’s waterfront development, how wind actually moves a boat, what it means to read the weather on the lake. People walk away having learned something they didn’t expect to learn, which makes the experience stick.
We’re also the operator that other boat companies in Toronto refer their overflow to. When a group calls one of the large cruise operators asking for 25 people, they’re too small for those vessels. Many of those companies send that call our way. We’re the right-size, right-format option for corporate groups who don’t need — and don’t want — a floating ballroom.
I’ve been sailing Lake Ontario for decades. My captains have between 10 and 50 years on the water. There’s a moment that happens on almost every corporate charter — usually somewhere past the Islands, when the city has receded a little and the boat is moving in silence — where someone looks up from their conversation and realizes where they actually are.
That moment is what I built Gone Sailing Adventures around. Not the sailing itself. The experience of someone discovering that sailing is something they can do, something they enjoy, something that changes how they see their city and their colleagues.
A $50 Groupon ticket once turned into years of sailing, a boat purchase, and a trip to the Bahamas. We’ve had people show up on a corporate charter because their manager told them to, and leave asking about lessons. That’s what a first experience can do.
Fair Winds,
Captain Howie Colt, Founder — Gone Sailing Adventures
When considering chartering a yacht in Canada, we know you have many options. Some of these options look super exciting and at ridiculously great prices. Recent trends in the industry have opened the door for many unqualified individuals to purchase boats and offer charter services to the unsuspecting public. It’s easy to create a website and even easier to just list a boat on sites such as Facebook Marketplace, Kijiji, Getmyboat, Boat Setter and many others.
Unfortunately, many of these operators are NOT licensed, insured or qualified to accept your trust on the water.
In order to be licensed and insured a number of items MUST be in place. Listed are just a few.
Over the last few years there have been a number of deaths and even more accidents resulting from these types of operators. Be safe and know who you are getting on a boat with. All licensed operators should willingly display their credentials, and most are members of the Passenger & Commercial Vessel Association (PCVA).
