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Experience Toronto's stunning skyline and Lake Ontario aboard a shared sailing trip. Relax, enjoy the views, or take the helm with no prior experience needed.
Imagine gliding across Lake Ontario, with the Toronto skyline shimmering in the background—a peaceful yet exciting way to see the city from a different perspective. That’s exactly what the 2-hour Shared Sailing Experience offers. Though we haven’t personally taken this trip, reviews and detailed descriptions paint a vivid picture of an enjoyable, well-organized outing suitable for anyone eager to enjoy Toronto’s waterfront without the hassle of boat ownership.
What makes this experience stand out? First, its small-group setting ensures you won’t be lost in crowds, and second, the chance to enjoy breathtaking views of the city’s iconic landmarks. On the downside, it’s weather-dependent, so a rainy day might mean a cancellation or reschedule. Still, if you’re looking for a relaxed, scenic activity that’s perfect for solo travelers, couples, or small families, this sailing adventure hits the spot.
This trip is ideal for those who want an authentic taste of Toronto’s waterfront, whether they have sailing experience or not. It’s particularly great for travelers seeking a calm, scenic break from busy city streets, and who appreciate the personal touch of small-group outings. If you’re hoping to snap photos of the skyline, enjoy some peaceful sailing, or even participate in the sailing itself, this tour offers plenty of flexibility.
Sailing fans have several other Toronto options to choose from
From the moment you arrive at 415 Queens Quay West—an accessible spot near public transportation—the feeling is one of anticipation. The crew from Gone Sailing Adventures is noted for their professionalism and warmth, making sure every guest feels welcome and safe right from the start.
Once aboard, the vessel comfortably accommodates up to 12 travelers, creating an intimate environment. The licensed captain takes charge, steering the boat smoothly past Toronto’s most famous sights, including the towering CN Tower and other skyline highlights. You’ll find yourself enjoying scenic vistas of Humber Bay and the eastern beaches, with plenty of opportunities for photos.
What really sets this trip apart is the flexibility to participate or relax. Many reviews praise the crew’s friendly attitude and willingness to involve guests—whether you want to take the helm or just sit back in a beanbag with a blanket and soak in the scenery. One review even mentions enjoying some Prosecco for sale, adding a touch of celebration to the cruise.
A highlight for many is the chance to capture the Toronto skyline at sunset or during daylight, with the boat gliding just far enough from the shore to enjoy unobstructed views. Some guests mentioned how peaceful it was when the engine was turned off, just sailing with the wind, and the views became even more stunning and serene.
The onboard amenities help you relax—the beanbags on the foredeck offer a comfy spot for lounging, and blankets are available if the weather turns cool. This thoughtful approach to comfort keeps the focus on enjoyment rather than discomfort. The crew’s professionalism and courteous manner make the experience feel safe and well-organized.
Several reviews mention the crew’s friendliness and the genuine, warm atmosphere onboard. For example, one guest said, “JC and Donna made you feel like family,” which points to the personal touch that differentiates this sailing experience from larger, more commercial tours.
More ways to experience Toronto from the water include these boat tours
At $140.10 per person, this experience offers quite good value given the scenic beauty and personalized service. Compared to other Toronto water tours that can be longer or more commercial, this small-group sailing provides an authentic, relaxed atmosphere—perfect for those who want a quality experience without feeling rushed or crowded.

Your journey begins at the meeting point near Queens Quay, where the crew will welcome you aboard. After a quick safety briefing, you’ll set sail into Toronto’s harbor. The captain will lead the way, choosing the best routes to showcase the city’s highlights.
You can expect to cruise past Humber Bay, where the waters are calmer, and enjoy panoramic views of the Toronto skyline. As you near the eastern beaches, the scenery shifts to a more relaxed, lakeside feel. During the cruise, you’ll be free to sit in the cozy beanbags or participate in sailing if you’re feeling adventurous—taking the helm is optional.
Throughout the trip, the crew keeps safety a priority, and the atmosphere remains casual. Many guests comment on the perfect balance of relaxation and engagement, with some even noting that they felt like “master and commander” for a little while.
The trip concludes back at the starting point, leaving you with plenty of time to explore more of Toronto’s waterfront or hop on nearby public transit.
The overwhelmingly positive reviews speak volumes: all 23 reviews rate it a perfect 5 out of 5. Guests consistently mention how breathtaking the views are, especially the Toronto skyline and sunsets. One reviewer described the trip as “super relaxing,” highlighting the wind and the crew’s dedication to safety and comfort.
Another praised the crew, saying, “Captain ROB and His Helper ROB were excellent,” emphasizing the professionalism and friendly attitude that made the trip a delight. Several reviews also mention that this was their first sailing experience, and they would happily repeat it, which speaks to the accessible, welcoming nature of the tour.
Guests appreciated the peaceful sailing when the engine was off, describing it as “very relaxing and romantic.” The opportunity to sit in comfortable blankets, listen to your own music through a Bluetooth speaker, and watch the sunset became a memorable highlight for many.
The small-group format, often described as “well-organized,” ensures a more personal experience—further reflected in comments like “the crew made you feel like family.” For those seeking genuine, less commercialized encounters with Toronto’s waterfront, this tour hits the right note.

This sailing adventure offers an enjoyable, laid-back way to see Toronto from the water. The combination of stunning views, friendly crew, and relaxed atmosphere makes it a standout choice for anyone wanting to detach from the city’s hustle for a couple of hours. It’s especially appealing for those who appreciate authentic experiences that aren’t overly commercialized but still feel special—like a little escape.
For travelers seeking a family-friendly activity or a romantic outing, the trip’s gentle pace and beautiful scenery will resonate. The small-group setting ensures personalized attention, making it feel more like a friendly boat trip with friends than a large tour.
While weather can be a gamble, the tour’s flexibility and the quality of the reviews suggest that most will find it well worth the price. The fact that every review is perfect speaks to consistent satisfaction, making this a dependable choice for a memorable Toronto outing.
“Amazing experience.. Team was so welcoming and incredibly courteous, professional and warm. Everything was well organised. Not to forget, the views…”
Is this sailing experience suitable for beginners?
Yes, no prior sailing experience is required. The licensed captain handles the boat, and guests can choose how much they want to participate.
How long does the tour last?
The trip lasts about 2 hours, providing ample time to enjoy the scenery without feeling rushed.
What should I wear?
Bring layers and a hat, especially if it’s sunny. Blankets are available if it gets chilly, and comfortable clothing is recommended.
Can I participate in sailing activities?
Yes, you can participate as much or as little as you like. You may take the helm if you wish, or simply relax on the deck.
What’s included in the price?
The fee covers the licensed captain and the vessel. Beverages are not included, but you can purchase Prosecco onboard.
Is the tour affected by weather?
The tour requires good weather. If canceled due to poor conditions, you’ll be offered a different date or a full refund.
This 2-hour shared sailing experience offers travelers an authentic, relaxing way to enjoy Toronto’s waterfront. Whether you’re celebrating a special occasion or simply want a peaceful break from city life, it’s a well-organized trip with consistently positive reviews that highlight the stunning vistas and friendly crew.