Gone Sailing Adventures runs private corporate team building experiences for groups of 10 to 40+ people, with a format built around what actually creates connection, not just proximity.
We split larger groups across multiple yachts with 8–12 people each, which means your team isn’t just standing next to their usual desk neighbours — they’re navigating Lake Ontario with colleagues they don’t normally work closely with. For the final stretch, we bring the whole fleet together on the water so the full group reunites with stories to trade.
For teams that want more structure, our 3-hour team challenge format runs like a friendly competition: a fleet-wide poker run where each boat earns a playing card at every mark on the course, combined with on-water challenges including knot-tying, phonetic alphabet drills, and the historic flag communication system to send messages between boats to earn more cards. The best hand at the dock wins.
For teams that want something more relaxed, a 2 or 3-hour social sail gives everyone a chance to take the helm, see the Toronto skyline from the water, and connect in a low-pressure setting that most people have simply never experienced before. The perfect opportunity for a group selfie.
Your group arrives at 415 Queens Quay West on the Toronto waterfront. We handle the welcome, the safety briefing, and every logistics detail. You just show up.
Your Transport Canada licensed captain takes the helm as your team heads out past the Toronto Islands. Whether you've chosen the social sail or the team challenge format, the experience is private, active, and genuinely unlike anything most of your group has done before.
The dock is where everyone's still talking. The office is where they're already asking when they're going again. That's the measure of a team building event that actually worked.
When people step away from their desks, their screens, and the usual office hierarchy, something changes. Conversations happen more naturally. The quiet ones come forward. The competitive ones find a new outlet. And the colleagues who’ve sat three desks apart for two years finally have a real reason to talk.
Sailing accelerates that shift because it’s a genuine first-time experience for almost everyone. In a group of 30, you might have one person who’s sailed before. That means the VP and the junior analyst are learning the same thing at the same time — and that shared starting point is what makes the connection real rather than forced.
Howie Colt, Gone Sailing Adventures’ founder and captain, describes it this way: “We create unforgettable experiences connecting people with the water, with the waves, with the wind, and with each other.”
His captains bring between 10 and 50 years of sailing experience to every corporate outing. Gone Sailing Adventures is fully licensed by Transport Canada and the Alcohol & Gaming Commission of Ontario, and carries a comprehensive risk management program — the same program that satisfied Shell Oil’s formal corporate risk assessment process when they brought a group to Toronto for a company event and then came back the next year.
If your company requires vendor safety documentation before approving an external event, we have it ready.
When your team leaves the office environment entirely and steps into a genuinely unfamiliar setting, the usual dynamics shift. The person who dominates every meeting is asking questions alongside everyone else. The introvert who stays quiet in group discussions ends up at the helm with the whole boat watching. And the colleague nobody’s properly spoken to in months turns out to be the one who masters the flag communication challenge.
That shift isn’t manufactured — it happens naturally. Being out on Lake Ontario is a real, shared experience with real stakes, guided by an experienced crew. As the group settles in and takes in the experience together, those moments of shared discovery and interaction are what build genuine trust and connection that carry back into the workplace.
Gone Sailing Adventures has run corporate team building events for engineering firms, financial services companies, sales organizations, legal teams, and technology companies across Toronto. Our approach is flexible enough to work for a relaxed department social and structured enough to satisfy a formal team building brief. And our safety program — developed through years of corporate events and tested against the risk management requirements of major clients including Shell Oil — means the person who organized this event doesn’t have to worry about the details going wrong.
I am continually amazed at the power of first experiences.
I’ve been sailing Lake Ontario for decades, and my captains have between 10 and 50 years on the water between them. What keeps all of us here, season after season, isn’t the sailing itself — it’s watching what happens to people the moment they realize they’re actually doing it.
The sceptic who signed up because their manager told them to is suddenly asking to take the helm. The team that arrived at the dock in separate clusters is leaving the dock as a group. And somewhere in the middle of it — between the first tack and the final approach back to Queens Quay — someone experiences something they genuinely didn’t expect.
That’s the moment we build every corporate team building event around.
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).
