Private Sailing in downtown Toronto

If you’re thinking about adding a touch of nautical charm to your Toronto trip, the Private Sailing in downtown Toronto experience might catch your eye. While I haven’t personally sailed this route myself, I’ve looked into it closely and talked to folks who’ve done it. The idea of cruising around the Toronto Islands with a knowledgeable captain, all while soaking in some of the best city views, sounds pretty appealing—especially for those who want a personalized, intimate perspective of the city from the water.

What I really love about this experience is its flexibility. It’s a private tour, so you won’t be stuck in a crowded group. Plus, at just $83 per person, it offers a unique way to enjoy Toronto’s skyline without breaking the bank. On the flip side, a key consideration is that transportation to the islands isn’t included, so you’ll need to plan your ferry trip to Hanlans Point. Overall, if you’re after a relaxing, picture-perfect outing with a dash of sailing, this could be a good fit—particularly for couples, small groups, or anyone who loves the idea of a tailored boat ride right downtown.

Key Points

• Intimate, private experience tailored for small groups or couples
• Stunning cityscape views from the Toronto Islands
• Opportunity to learn basic navigational skills or even try steering the boat
• Ferry to the islands not included, so plan accordingly
• Duration is roughly 1 hour, mostly available in the afternoon
• Experience is guided in English and offers flexible booking options

You can check availability for your dates here:

What Makes This Sailing Tour Stand Out

The main draw of this tour is its personalized nature. Unlike big cruise ships or group tours, this is a private experience, often with a captain who’s eager to share local insights and help you get the best photos possible. It’s clear from reviews that the captain’s knowledge and friendly attitude make a difference, creating a relaxed atmosphere that feels more like visiting a friend than joining a commercial tour.

The spectacular views of Toronto’s skyline are what many people rave about. As you cruise around the Toronto Islands, you’ll be treated to close-up vistas of the city’s iconic skyscrapers, framed beautifully by the water. It’s the kind of experience that’s especially stunning during the late afternoon, when the light hits just right for photos.

Another highlight is the opportunity to learn the basics of sailing. If you’re curious about becoming a sailor someday, this is a nice intro. The captain is happy to teach some fundamental navigational skills or even let you drive the boat if you’re interested—an experience that adds a little extra to an hour-long cruise.

What to Expect: The Details

Starting point: The tour departs from the Toronto Islands, specifically after taking a ferry to Hanlans Point and walking about 10 minutes to the boat parking area. Keep in mind that transportation to the islands is not included, so you’ll need to plan your ferry ride accordingly. The ferry itself is a simple, scenic way to get there, and the walk to the boat is easy.

On board: You’ll be on a sailboat with a captain, which means the experience is intimate and relaxed. The boat is well-equipped, and from reviews, it seems the captain is attentive and eager to share his knowledge.

Duration: Just about 1 hour, generally offered in the afternoon. Given the short time, it’s perfect for fitting into a broader day of sightseeing or relaxing on the water.

Activities: Besides enjoying the sights, the captain will suggest fun ways to pose for photos—ideal for social media. If you’re up for it, you can even get behind the wheel or learn basic navigational skills, adding an interactive element to the cruise.

Inclusions: The sailboat and captain are included in the price. You won’t pay extra for the boat or guide.

Exclusions: Transportation to the islands is on you. You’ll need to take the ferry to Hanlans Point and walk to the boat.

Cancellation & Payment: You can cancel up to 24 hours in advance for a full refund, giving you some peace of mind if your plans change. You can also reserve now and pay later, which is handy when planning ahead.

Who Will Love This Tour?

This experience is best suited for adventurers who want a personalized, scenic outing. It’s great for couples looking for a romantic escape, small groups wanting a memorable photo session, or anyone interested in a brief sailing lesson. It might also appeal to travelers who prefer a quiet, private experience rather than a crowded tour.

While it’s not explicitly marketed as family-friendly, the relaxed, short nature of the cruise makes it accessible to most ages—though young children should be supervised around water and on the boat.

The Value of a One-Hour Private Sail

At $83 per person, this tour easily compares favorably with other waterfront activities in Toronto. The value lies in its personalized approach and the chance to capture stunning photos against Toronto’s skyline. It’s a way to see a different side of the city—softer, more intimate, and relaxed—than the usual busy sightseeing tours.

The opportunity to learn or try sailing basics is a bonus for those curious about the nautical side of Toronto. Plus, the private setting means you won’t be rushed or crowded, which makes for a more enjoyable experience.

However, keep in mind that the experience relies heavily on weather conditions. Calm, sunny days will deliver the best views and most enjoyable sailing. If the forecast calls for storms or high winds, the captain might reschedule or the experience could be less pleasant.

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Final Thoughts: Is This the Right Tour for You?

This private sailing adventure will shine for anyone wanting a personalized, scenic, and relaxed way to see Toronto from the water. If you love taking photos, learning a bit about sailing, or simply enjoying a peaceful cruise with a view of the city’s skyline, this tour hits the right notes.

It’s especially well-suited for couples or small groups seeking something intimate and special without a hefty price tag. The short duration makes it easy to fit into a busy itinerary, and the private setting ensures a tailored experience. Just remember that transportation to the islands isn’t included, so plan your ferry trip accordingly.

If your idea of a perfect outing involves stunning views, friendly guides, and a chance to try your hand at sailing, this tour is worth considering. But if you’re after a longer, more extensive cruise or need a family-friendly, kid-focused outing, you might want to explore other options.

FAQs

Do I need sailing experience to join?
Not at all. The captain provides some basic navigational guidance and is happy to teach if you’re interested. It’s primarily a scenic cruise, not a sailing lesson series.

Is the tour suitable for children?
While not explicitly marketed as family-friendly, the short duration and relaxed environment could work for children, provided they are supervised around water and on the boat.

How do I get to the departure point?
You take a ferry to Hanlans Point on the Toronto Islands, then walk about 10 minutes to the boat parking area. Remember, transportation to the islands isn’t included in the tour price.

What should I bring?
Dress comfortably and consider bringing sunglasses, sunscreen, and a camera. Since it’s a boat trip, a light jacket or windbreaker might be helpful if it’s breezy.

Can I cancel if my plans change?
Yes, you can cancel up to 24 hours in advance for a full refund. You can also reserve now and pay later, which adds flexibility.

What time of day does the tour usually run?
Most experiences are available in the afternoon, ideal for catching the sunset or afternoon light.

Is the boat covered or open?
The tour is on a sailboat, which is generally open but may have some shaded areas. Dress for the weather.

How long is the experience?
About 1 hour, making it easy to fit into a busy day of sightseeing or relaxation.

What if the weather is bad?
The tour can be canceled or rescheduled, and you’ll receive a full refund if you cancel at least 24 hours in advance.

If you’re after a peaceful, personalized way to enjoy Toronto’s waterfront and skyline, this private sailing trip offers a lovely blend of scenery, learning, and photo opportunities. Just be sure to plan your ferry ride to the islands, and you’re all set for a charming water adventure.

You can check availability for your dates here: