Company Outing & Corporate Retreat Toronto: Private Sailing on Lake Ontario

A company outing should feel like a reward, not another obligation. Gone Sailing Adventures offers private sailing experiences on Lake Ontario — designed for corporate groups that want something genuine, memorable, and easy to get behind. Whether you're planning an internal team social, a leadership retreat, or a client entertainment event, we depart from 415 Queens Quay West in downtown Toronto with captains who bring 10 to 50 years of experience to every outing. Groups of 10 to 40+. No sailing experience required.

A company outing that actually works for everyone is harder to plan than it looks.

You need something that appeals across the whole group — not just the people who already like each other, not just the extroverts, and not just the ones whose idea it was. It has to feel worth the time away from work, hold up to leadership scrutiny, and ideally be something people don't groan about when you announce it.

Most company outings in Toronto fall into familiar traps:

A dinner reservation that turns into a two-hour conversation with the two people adjacent
A loud activity venue where half the group checks out early
A "retreat" that feels like a meeting with better catering

The best company outing creates space for real connection — not just proximity. Sailing does that naturally.

A private sailing experience on Toronto Harbour — for company outings, retreats, and client events.

Gone Sailing Adventures runs private corporate sailing experiences designed for two types of groups: internal teams that want to connect outside the office, and companies that want to entertain clients in a setting that feels elevated and thoughtful.

Both use cases come up naturally in the corporate world — and both are served well by sailing. For team outings, it's the shared novelty that does the work: most people in your group have probably never sailed before, which means nobody arrives as the expert, and everyone experiences something genuinely fresh and new together. For client events, sailing signals something different from the standard lunch, hospitality venue or common round of golf. It's high-class, private, scenic, and memorable in a way that reflects well on the company that booked it.

Either way, you're leaving the office and going somewhere real — with the Toronto skyline and islands behind you and Lake Ontario on the horizon.

Meet at Our Waterfront Dock

Your group arrives at 415 Queens Quay West, right on the Toronto waterfront. We handle the welcome, the safety briefing, and everything else. You just show up.

Set Sail Privately on Lake Ontario

The city falls away the moment you leave the dock. Your captain and crew handle the sailing — your group handles the conversation. Whether you're running a 2-hour social sail or a 3 or 4 hour structured experience, the atmosphere is relaxed, private, and entirely yours.

Come Back with Something Worth Talking About

The best company outings are the ones people reference for months afterward. We create this every time we leave the dock.

A stronger choice than another restaurant, venue, or indoor group activity.

The case for sailing as a company outing or corporate retreat experience comes down to one thing the alternatives can't replicate: genuine novelty shared across the whole group.

In a team of 30, you might have one person who's sailed before. That means everyone else — from the junior staff to the VPs — arrives at the same starting point. Nobody has the upper hand. Nobody can hang back and let the experts do the interesting part. That engagement creates a connection that carries back into the workplace.

Gone Sailing Adventures has run corporate outings for engineering firms, financial services companies, legal teams, and sales organizations across Toronto. We're fully licensed by Transport Canada and the Alcohol & Gaming Commission of Ontario. We have a comprehensive risk management program — developed through experience with major corporate clients including Shell Oil — and can provide full safety documentation for companies that require vendor compliance sign-off before approving an event.

If you're the person who has to present this to leadership or get it through a risk management review, we make that part easy.

  • Private sailing for corporate groups of 10–40+
  • 2-hour social sail or 3-hour structured team challenge format
  • Customized to your specific requirements
  • Transport Canada licensed — risk management documentation available
  • Departs from 415 Queens Quay West, downtown Toronto
  • Captains with years of sailing experience
  • Suitable for internal team outings, leadership retreats, and client entertainment
Hot Flash – Sailing Yacht

Professional, licensed, and built for corporate planning.

Corporate events carry a different kind of weight than personal outings. There are internal approvals, risk considerations, and guest expectations to manage — and when it goes wrong, it reflects on the person who booked it. We understand that dynamic because we’ve worked with corporate clients who take those considerations seriously.

Gone Sailing Adventures operates under Transport Canada licensing with a risk management manual developed over years of running corporate events on Lake Ontario. Our captains bring between 10 and 50 years of experience to every outing. When Shell Oil brought a group to Toronto for a corporate event, we provided a full two-page executive risk assessment — a summary of our 50-page risk management program — covering potential risks and mitigation factors for every aspect of the outing. That’s the level of documentation we can produce when your company needs it.

For the office administrator or HR manager tasked with organizing this event: we’re the vendor that makes your job easier, not harder. We communicate clearly, show up prepared, and run a clean, professional experience from initial inquiry to disembarking.

Frequently Asked Questions

Is this better suited for team outings or client entertainment?

It works well for both, and the format adjusts accordingly. For internal team outings, we focus on connection and shared experience. For client entertainment, the experience feels polished and distinctive — a strong alternative to the standard golf game, client lunch or hospitality venue. We've hosted both types of events for Toronto & International companies across a range of industries.

Yes, with a practical note: it works best as a focused retreat experience or a retreat component rather than a full multi-day program. It's a strong choice for companies that want to bring their leadership team or a key group together in a setting that removes them from the normal office environment and creates space for real conversation.

Yes. We have a comprehensive risk management program and can provide documentation for companies that require a formal vendor safety review. We've done this for major corporate clients including Shell Oil, and the process is straightforward.

None at all. Your Transport Canada licensed captain and experienced Mate handles the sailing. Your group just shows up and enjoys the outing — unless of course, you want to sail; instruction included.

Where do you depart from?

415 Queens Quay West, Toronto — at the Spadina wavedeck on the waterfront. It's accessible by TTC (Spadina streetcar to Queens Quay), GO train from Union Station, and on foot from much of downtown Toronto's office core.

We work with groups of 10 to 40+ people. Larger groups sail across multiple yachts and reunite on the water; smaller groups (<12) can stay together on one vessel.

Comfortable, weather-appropriate clothing. We'll provide guidance in advance of your outing.

We monitor conditions closely and communicate early. Most weather is manageable on Lake Ontario — our captains have 10 to 50 years of experience reading conditions. For severe weather, we work with you on rescheduling. Your group's experience and safety come first. We also offer Weather Protection as an additional option.

I am continually amazed at the power of first experiences.

I’ve been sailing Lake Ontario for decades. My captains have between 10 and 50 years on the water. And the thing that keeps all of us coming back — every season, every outing — is watching what happens to people the first time they step aboard.

The colleague who was quiet the whole way to the dock is suddenly at the helm, laughing, asking questions. The executives who spent the morning in back-to-back meetings are sitting on the bow talking about something that has nothing to do with work. The client who came out of obligation is asking about lessons.

That’s what a first experience does. It creates a before and after. And it’s what we build every company outing and corporate event around.

Fair Winds,

Captain Howie Colt, Founder — Gone Sailing Adventures

Book your preferred date before the season fills up.

Corporate and client sailing dates on Toronto Harbour fill quickly from May through October, often 4 to 12 weeks out. The earlier you reach out, the more flexibility you'll have on timing, format, and group size. If you're working toward a specific date or coordinating multiple schedules, now is the right time to start.

Whether you're planning a company outing, a retreat-style experience, or a client entertainment event, we're straightforward to work with and quick to respond.

Gone Sailing Adventures · 415 Queens Quay West, Toronto, ON M5V 1A2 · (416) 240-0202 Operating on Lake Ontario, Toronto Harbour, and the Toronto Islands, spring through fall.

Testimonials
What Our Guests Say

Corporate Event Request

YOUR SAFETY IS AT RISK

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.

  • The operator must be licensed by Transport Canada with a commercial license known as either:
    – Limited Master under 60tonne.
    – Small Vessel Operators Permit (SVOP).
  • The name of the vessel must be visible on the stern (back) or the registration number beginning with the letter “C” must be visible on the side of the vessel near the front. Boats with a registration number beginning with “ON” are not licensed for passengers.
  • If the vessel is under 12m (40’) it should participate in the Transport Canada Small Vessel Compliance Program and display a “Blue Decal” and have corresponding certificate.
  • If the vessel is over 12m (40’) or carries more than 12 passengers, it MUST BE INSPECTED by Transport Canada and have an inspection certificate on board.
  • All vessels must have commercial liability insurance and coverage specifically for the number of passengers approved to be carried on board.
  • The vessel must comply with commercial safety requirements beyond recreational standards. Many of these illegal operators do not have the proper training, carry proper safety equipment, nor do their recreational boats meet the design/construction requirements of a commercial, passenger carrying vessel. These illegal operators try to stay under the radar of Police/OPP/RCMP/Transport Canada by:
  • hiding the name of their vessel by hanging items over the stern
  • not letting you know where they will have you board until just before the start of your charter.
  • pick you up at a public park (where docking is not permitted).
  • suggest to you that you are friends of the owner/operator out for a ride and not a paying customer.
  • allow you to drink alcohol while the boat is underway (illegal-same as a car) but tell you to hide your bottles etc.
  • insist on a cash transaction or part of it as a way of defrauding the internet listing company.
  • Make you sign a “Charter Agreement” just before you board without giving you details of the document beforehand.

    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).

    Link to Global News Report on Charter Accidents

Check before you book
&
Know before you Go!