Private Sailing in downtown Toronto

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If you’re looking to see Toronto from a fresh perspective, a private sailing tour around the Toronto Islands offers an intimate and scenic escape just minutes from the city center. Though we haven’t personally jumped on this boat, extensive reviews and descriptions paint a picture of a relaxing yet exciting experience that combines breathtaking views, personalized interaction, and a touch of nautical adventure.

What we love about this experience is the chance to get stunning cityscape photos with the Toronto skyline as a backdrop, the opportunity for a romantic outing in downtown Toronto, and the relaxed, private nature of the tour. Plus, the possibility of learning a few basic sailing skills adds a fun, interactive element.

One thing to keep in mind is that transportation to the departure point isn’t included, so you’ll need to plan your ferry or transit to Hanlans Point. This experience is particularly well-suited for couples, small groups, or anyone wanting a memorable, personalized way to enjoy Toronto’s waterfront without the crowds or typical tourist hustle.

Good To Know

• Private, personalized experience with a knowledgeable captain
• Best views of Toronto skyline from the water
• Ideal for romantic outings or small groups
• Opportunity to learn basic sailing skills if interested
• Departure from Toronto Islands, requiring separate ferry transportation
• Flexible booking with free cancellation up to 24 hours in advance

You can check if your dates are available here:

An In-Depth Look at Private Sailing in Downtown Toronto

What Makes This Tour Special?

This tour offers a rare opportunity to enjoy the Toronto skyline from a personal sailboat. Unlike larger cruises, a private experience means you can tailor your outing—whether you want to take photos, relax, or get some hands-on sailing experience. The tour is designed to be informal and friendly, with a captain eager to share insights and help you capture perfect social media-worthy shots.

The Departure Point and Planning

The experience begins at the Toronto Islands, with guests needing to take a ferry to Hanlans Point. From there, it’s about a 10-minute walk to the boat parking area. This two-step process adds a layer of adventure and makes the entire outing feel like an escape from the city hustle. However, it’s worth noting that transportation costs and logistics are not included, so plan accordingly.

Duration and Timing

With a 1-hour window mostly available in the afternoon, this tour is perfect for a late-day escape when the city’s lights begin to twinkle and the water sparkles. It’s a short, sweet experience—ideal if you’re looking for a quick but impactful activity without committing to a full day.

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What’s Included?

A sailboat with a captain is the core of the experience, ensuring safety and expert navigation. The guide, who speaks English, is friendly and eager to meet guests, answer questions, and help you pose for memorable photos. If you’re interested in sailing, they might even let you try steering the boat, making it a hands-on learning experience.

What Isn’t Included?

Transportation to the departure point is on you, which can be a consideration if you’re not staying nearby or don’t want to navigate Toronto’s ferry system. The boat itself is private, which means no large crowds—just your group and the captain.

The Experience Itself

Expect to glide smoothly past the Toronto Islands, with the skyline as the backdrop—a view that’s especially striking at sunset or during golden hour. The captain is praised for their knowledge and friendliness, often sharing tips for posing for photos or capturing the perfect shot. Some reviewers mentioned that the captain even offers some basic sailing lessons, adding a unique, interactive element that elevates the tour beyond just sightseeing.

What Reviewers Say

One reviewer noted, “The guide was super friendly and knew exactly how to get the best angles for photos, making the whole experience really special.” Others appreciated the quiet serenity of sailing away from the crowds, emphasizing how peaceful the water was compared to busy waterfront promenades. The 1-hour duration was described as “just right”—enough to enjoy the views without feeling rushed.

The Value for the Price

At $83 per person, this private sailing seems quite reasonable, especially considering the exclusivity and personalized attention. It’s a great way to splurge on a unique, scenic experience without the hefty price tag of larger cruises or dinner tours. Plus, the flexibility of booking with free cancellation offers peace of mind.

Who Would Love This?

This tour is perfect for couples seeking a romantic outing, small groups of friends, or anyone wanting a personalized, scenic water adventure. It’s especially appealing if you love photography or are interested in a more authentic sailing experience, away from commercialized tours.

Practical Tips for Your Sailing Adventure

• Dress comfortably and consider bringing a light jacket—winds can be cooler on the water.
• Plan your ferry or transportation to Hanlans Point in advance to avoid last-minute stress.
• Bring your camera or smartphone for capturing views and fun selfies.
• If you’re interested in learning to sail, express this when booking—your captain is happy to teach some basic skills.
• Arrive a few minutes early to get settled and introduce yourself to the captain.

Final Thoughts

A private sailing tour in downtown Toronto offers a memorable blend of scenic beauty, personalized service, and a touch of nautical fun. With stunning panoramic views of the city skyline against a peaceful water backdrop, it’s an experience that can elevate your visit—whether you’re celebrating a special occasion or simply craving a unique way to see Toronto.

While the logistics of getting to the departure point require some planning, the effort is well worth it for the intimacy and exclusivity of this experience. The knowledgeable captain, who doubles as a friendly guide and photo assistant, ensures you’ll leave with more than just photos—you’ll have a story to tell.

This is best suited for travelers who value quality over quantity, enjoy a little adventure, and want a beautiful, private perspective on Toronto’s waterfront. If you’re after a relaxing, picturesque, and customizable outing, this sailboat experience offers excellent value and genuine charm.

FAQ

Do I need my own transportation to the departure point?
Yes, transportation to the Toronto Islands isn’t included. You’ll need to take the ferry to Hanlans Point and then walk about 10 minutes to the boat parking.

How long is the tour?
The experience lasts approximately 1 hour, usually available in the afternoon, making it perfect for a short, scenic escape.

Is this a group tour or private?
It’s a private tour, meaning only your group will be on the boat with the captain, providing a personalized experience.

What’s included in the price?
The price covers the sailboat and the captain guiding and assisting you during the trip.

Can I learn to sail during the tour?
Yes, if you’re interested, the captain may offer to let you steer the boat and learn some basic navigational skills.

What should I wear?
Comfortable clothing suitable for being on the water, and consider bringing a light jacket as it can be breezy.

Are there any hidden costs?
Transport to the departure point isn’t included, so budget for ferry or other transit costs separately.

Is this experience suitable for children?
While not explicitly stated, the private nature and relaxed environment could make it suitable for families, provided children are comfortable on the water.

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

A private sailing in downtown Toronto offers a delightful mix of scenic views, personal touch, and nautical fun — perfect for those wanting to see the city from a different angle without the crowds.

You can check if your dates are available here: