Private Sailing in downtown Toronto

Private Sailing in Downtown Toronto: A Personal Voyage with Spectacular Views

If you’re looking to add a touch of elegance and adventure to your Toronto visit, private sailing offers an intimate way to see the city’s iconic skyline. For just $83 per person, you’ll spend an hour aboard a personal sailboat, cruising around the Toronto Islands while taking in panoramic views that are hard to beat. Your guide, a friendly captain, will not only steer you past the city’s shimmering skyscrapers but also share tips for the best photo angles and even offer you a chance to try your hand at navigating the boat.

What truly makes this experience stand out is the personalized nature of the tour — it’s a private group setting, which means you can relax and enjoy without the crowds. Plus, the spectacular backdrop of Toronto’s skyline creates a perfect setting for memorable photos, romantic moments, or just a peaceful escape from the urban hustle.

One thing to consider is that the tour departs from Hanlans Point on the Toronto Islands, requiring you to take the ferry there, which adds a bit of logistical planning. Beginners might want to be comfortable with boat safety, as this is a true sailing experience, not a sightseeing cruise on a large vessel.

This tour will appeal most to couples seeking a romantic outing, groups of friends wanting a unique experience, or anyone eager to see Toronto from a fresh vantage point. If you enjoy personalized, scenic adventures with a splash of sailing, this could be your highlight.

Key Points

• Personalized Experience: Private group with a captain, offering a tailored sailing adventure.
• Spectacular Views: Unbeatable angles of the Toronto skyline and Islands that are perfect for photos.
• Learning Opportunity: Chance to get hands-on experience with basic navigation if you’re interested in sailing.
• Logistical Considerations: You need to take a ferry to the Islands, as transportation isn’t included.
• Flexible Booking: Cancel up to 24 hours in advance for a full refund, with the option to reserve now and pay later.
• Duration: A full hour on the water, usually scheduled in the afternoon for optimal lighting and weather.

You can check availability for your dates here:

A Closer Look at the Toronto Sailing Experience

When we think of Toronto, images of tall buildings and bustling streets often come to mind. But from the water, the city takes on a different personality — one that’s peaceful, yet filled with stunning vistas. This tour offers a chance to see the Toronto skyline from a unique perspective, with the Toronto Islands adding a natural touch to the urban scenery.

The Departure Point and Logistics

The tour departs from Hanlans Point on the Toronto Islands, accessible by a short ferry ride from the mainland. The walk from the ferry dock to the boat parking area takes about 10 minutes, so you’ll want to factor in that extra bit of time. Once aboard, you’ll meet your captain — the guide and boat owner — who is eager to share his knowledge and ensure you get the most out of your hour on the water.

The Itinerary and What You’ll Experience

Your hour-long sailing adventure begins with a warm welcome aboard. As you settle into the boat, the captain will give a brief safety overview and then start guiding you around the islands. You’ll likely cruise past the Toronto Islands, which includes spots like Ward’s Island and Centre Island, offering views of lakeside cottages and lush greenery contrasting with the cityscape.

The highlight, of course, is the view of downtown Toronto, where skyscrapers like the CN Tower and Rogers Centre create a striking silhouette against the sky. Your captain, who is attentive and friendly, will suggest great ways to pose for photos — whether it’s leaning against the rigging, sitting on the bow, or capturing the city reflected in the water.

Photography and Social Media Opportunities

One of the most praised aspects of this tour is the photo-friendly environment. The captain actively offers tips for the best angles and even takes photos of you, making it easier to get those perfect shots for Instagram or memories. Expect to snap images of the skyline, the sailcloth billowing in the breeze, and the peaceful waters around the islands.

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Sailing and Learning Experience

For those curious about sailing, there’s a bonus — the captain might invite you to try steering the boat or learn some basic navigational skills. This isn’t a disembodied cruise; it’s an interactive experience that can be as relaxed or hands-on as you like. For beginners, this can be a fun way to dip your toes into sailing, while seasoned sailors will appreciate the opportunity to see the city from the water.

What We Love About This Tour

We especially appreciate the personal attention you get with this private experience. Unlike large boat cruises, this is about quality over quantity — you won’t be jostling for space or fighting over the best photo angles. The spectacular cityscape views are another major plus. Seeing Toronto from the water offers a fresh perspective that’s both romantic and inspiring — especially at sunset or in the late afternoon when the light is perfect.

The Value of the Experience

While $83 per person might seem modest for a private sailing expedition, it’s important to consider what’s included: a personalized boat with a captain and a full hour of sailing with photo opportunities and some sailing lessons. Compared to larger cruise options, you get a more intimate, flexible, and engaging experience. Keep in mind, transportation to the islands is not included, so budget extra time and a small ferry fee.

The Price and Who It’s For

Given the small group size and personal touch, this tour represents great value for those wanting a special, memorable outing without breaking the bank. It’s especially suitable for romantic couples, small groups of friends, or solo travelers who enjoy nautical adventures and cityscapes.

Final Thoughts: Is It Right for You?

If you’re craving a different view of Toronto that’s less crowded and more personal, this sailing tour fits the bill. It’s a rare chance to combine gentle sailing, some basic navigational fun, and top-notch photo opportunities all in one hour. It’s also flexible enough to accommodate both sailing novices and seasoned enthusiasts, thanks to the captain’s friendly approach and willingness to teach.

However, do remember that the departure point requires a ferry journey, and if you’re not comfortable with boat safety or have mobility issues, you might want to consider other options. Still, for those who love the idea of drifting past Toronto’s skyline on a sailboat, this experience is a highlight waiting to happen.

In all, this private sailing adventure offers an authentic, scenic, and personalized way to enjoy Toronto’s waterfront. It’s a great choice for travelers seeking a peaceful yet visually stunning experience, with enough flexibility and charm to make your time on the water truly memorable.

FAQ

Do I need sailing experience to join this tour?
No, you don’t need prior sailing experience. The captain will guide you and is happy to show you the ropes or let you try steering if you’re interested.

How do I get to the departure point?
You’ll take a ferry to Hanlans Point on the Toronto Islands. The walk from the ferry dock to the boat parking area takes about 10 minutes. Transportation isn’t included, so plan accordingly.

What should I wear?
Dress comfortably and warmly, especially if it’s a breezy day. Layers are recommended since weather can change quickly on the water.

Is this tour suitable for children?
The tour is designed for private groups, so it’s best suited for adults or older children who are comfortable on boats.

How long is the tour?
The sailing itself lasts about 1 hour, usually scheduled in the afternoon to enjoy the best lighting and weather.

Can I cancel if my plans change?
Yes, you can cancel up to 24 hours in advance for a full refund, giving you some flexibility in planning your trip.

Whether you’re seeking a romantic escape, an outdoor adventure, or a chance to see Toronto from a different angle, this private sailing trip offers a charming and memorable way to experience the city’s waterfront. With stunning views, personalized attention, and a chance to learn a bit about sailing, it’s a practical and delightful addition to any Toronto itinerary.

You can check availability for your dates here: