Private Sailing in downtown Toronto

Imagine gliding across the waters of Lake Ontario, surrounded by Toronto’s majestic skyline, with only your private group and a friendly captain aboard. That’s what this private sailing experience offers—a chance to see the city from a different angle, in a relaxed, personalized setting. While it’s just an hour long, it packs in enough charm and scenery to make it a memorable part of your Toronto trip.

What makes this experience appealing? First, the spectacular views of Toronto’s iconic skyline from the water are truly breathtaking, especially for photographers and Instagram enthusiasts. Second, the personalized nature of a private tour ensures a flexible, intimate outing tailored to your group’s mood and interests. But it’s worth noting that transportation to the ferry point isn’t included**, which could add a little planning for travelers coming from downtown or other parts of the city. This tour suits couples, small groups, or anyone craving a calm, scenic break amid a bustling city.

Key Points

• Unique perspective: Offers a stunning, up-close view of Toronto’s skyline from Lake Ontario.
• Private & personalized: Customizable experience with a knowledgeable captain guiding your journey.
• Ideal for photos: Perfect for capturing memorable shots of the skyline and sailboat.
• Flexible and safe: Cancel up to 24 hours in advance with full refund, reservation with pay-later option.
• Accessible for romantics & adventurers: Romantic ambiance with the chance to learn basic sailing skills.
• Departure point: From the Toronto Islands, after a ferry ride from Hanlans Point.

You can check availability for your dates here:

Setting the Scene: Where and How

This tour begins on the Toronto Islands, a peaceful retreat just a short ferry ride from downtown. After arriving at Hanlans Point, you’ll walk about 10 minutes to the boat parking area—an easy, scenic walk that primes you for the adventure ahead. Since transportation isn’t included, it’s good to plan your ferry timing in advance, especially during busy periods. The departure is typically in the afternoon, aligning well with daylight hours for optimal photos and visibility.

What the Tour Includes

For $83 per person, you get exclusive access to a well-maintained sailboat with a captain at the helm. This private setup means no crowds, just your group soaking in the views and enjoying personalized attention. The boat’s captain isn’t just a driver but also a guide who will suggest the best poses for photos and help you snap shots that you’ll want to share for years.

The Experience Itself

The hour-long cruise is a chance for some quiet relaxation as you glide past the Toronto Islands and take in the spectacular city skyline—a view that’s especially striking at sunset or in the late afternoon light. The captain is friendly and knowledgeable, eager to share tips on sailing and navigation if you’re interested. It’s a relaxed environment, perfect for couples looking for romance or small groups wanting a unique city experience.

Photogenic Moments & Tips

We loved the way the captain offers suggestions for poses—leaning against the mast, sitting at the bow with the skyline behind, or capturing reflections in the water. If you’re into social media, this is a goldmine for eye-catching shots. The captain also promises to snap photos of you against Toronto’s impressive skyline, ensuring you get some great keepsakes.

More Great Tours Nearby

Learning and Engagement

For those curious about sailing, the captain is happy to let you steer the boat briefly and teach some basic navigational skills, turning a leisurely cruise into a mini sailing lesson. Even if you’re not familiar with boats, this adds a layer of fun and learning to the experience.

Scenery and Views

The highlights are undoubtedly the views of downtown Toronto from the water—sky-high skyscrapers like the CN Tower, Rogers Centre, and the Harbourfront blend into the shimmering lake. The scenery changes with the light, making each time of day uniquely captivating. Many reviews mention how the photos taken here are some of the best of Toronto’s skyline, perfect for capturing a memorable snapshot.

Considerations and Practical Tips

While the tour’s value is high, remember that it doesn’t include transportation to the islands—so if you’re staying downtown, factor in ferry or transit times. The tour is generally available in the afternoon, which aligns well with prime daylight hours for photography. As a private experience, group sizes are small, meaning it’s ideal for intimacy but may not appeal if you’re seeking a larger, social cruise.

Price & Value

At $83 per person, this is a premium but reasonable cost considering the exclusivity and personalized touch. The private nature means you won’t share the boat with strangers, and the guides’ attentiveness adds value—especially for couples, families, or small groups wanting something special. Compared to larger harbor cruises or dining options, this offers a more authentic, tranquil way to experience Toronto’s waterfront.

Authenticity & Reviews

Many travelers have highlighted the knowledgeable guides and stunning views as standout features. One reviewer remarked, “The captain was super friendly and suggested great photo spots,” while another appreciated the peaceful, intimate environment away from crowds. The ability to learn basic sailing skills also appeals to those wanting a hands-on experience.

This private sailing experience is best suited for travelers seeking a peaceful, scenic way to see Toronto from the water without the hustle of large boats or commercial tours. It’s ideal for romantic couples, small groups of friends, or even solo travelers who want a quiet, personalized adventure. If you’re a photography enthusiast or looking for a unique social media moment, this tour offers plenty of opportunities. And if you’re interested in sailing or learning navigation basics, the captain’s guidance makes it even more engaging.

However, if you’re on a tight schedule or not comfortable arranging transport to the ferry, you might want to consider how to coordinate your arrival. Also, those looking for a longer or more comprehensive cruise should explore other options, but for a quick, high-quality snapshot of Toronto’s waterfront, this is hard to beat.

This private sailing experience delivers a special, intimate glimpse of Toronto’s skyline from the water. The combination of spectacular scenery, personalized guide service, and the chance to learn a few sailing tricks makes it a memorable addition to any visit. While it’s a brief outing, its quality and authenticity make it well worth the price for those craving a peaceful, scenic break from city sightseeing.

It’s particularly suited to couples, small groups, or photography lovers wanting to capture Toronto in a unique way. If you’re after a calm, personalized adventure with excellent views and friendly guidance, this tour hits the right notes. Just remember to plan your ferry and transport so you can arrive relaxed and ready to enjoy the ride.

Do I need to bring my own transportation to the departure point? No, but you’ll need to take the ferry to Hanlans Point and then walk about 10 minutes to the boat parking. Transportation isn’t included, so plan accordingly.

How long is the tour? The cruise lasts about 1 hour, typically in the afternoon, providing plenty of time for sightseeing and photos without feeling rushed.

Is this tour private? Yes, it’s a private group experience, meaning you won’t share the boat with strangers, making it ideal for intimacy and tailored interactions.

Can I learn to sail during the tour? Absolutely! The captain is happy to let you steer the boat and teach some basic navigational skills, adding an interactive element.

What’s included in the price? The tour includes the sailboat and a captain but does not cover transportation to the ferry point.

Is there a full refund policy? Yes, you can cancel up to 24 hours in advance for a full refund, offering flexibility in case your plans change.

This detailed review aims to help you decide if this private sailing tour matches your interests and schedule. It’s a unique way to see Toronto from the water—peaceful, scenic, and personalized. Whether you’re celebrating a special occasion or simply want a quiet escape, it’s a charming, authentic experience that offers a fresh perspective on the city’s stunning skyline.

You can check availability for your dates here: