Sailing in Downtown Toronto
Set sail on a memorable sailing experience in downtown Toronto aboard a well-maintained 1997 Hunter 280. Perfect for small groups, this comfortable sailboat accommodates up to 6 guests, making it ideal for couples, families, or friends looking to explore the city from a unique perspective on the water.
Powered by a reliable 18 HP Yanmar diesel inboard engine, the boat offers smooth cruising at up to 6 knots, combining relaxed sailing with steady performance. Onboard, you’ll find everything you need for a comfortable and enjoyable trip, including an audio system, outside speakers, an ice box, and grill, perfect for creating your own atmosphere while cruising the waterfront.
Your captain, Domenic Grasso, brings experience in sailing tours, sunset trips, sightseeing, and canal boat experiences, ensuring a safe, relaxed, and enjoyable journey tailored to your group.
The boat is equipped with practical comforts such as a bathing platform, kitchen, one full bathroom with toilet, and ample space to relax and take in the stunning views of Toronto’s skyline and surrounding waters.
Included safety features such as GPS, VHF radio, anchor, and wheel steering provide peace of mind throughout your trip.
Guests are welcome to bring alcohol, children, and pets, and swimming is also allowed, making this a flexible and fun experience for all types of groups. Optional extras such as lunch can be arranged to enhance your time onboard.
Rates:
Monday–Thursday: $400 per couple or $100 per person (groups of 5–6)
Friday–Sunday & holidays: $500 per couple or $150 per person (groups of 5–6)
Whether you're celebrating a special occasion or simply looking to escape the city, this sailing trip offers a unique and unforgettable way to experience Toronto from the water. Book now and create lasting memories on the lake.
Set sail on a memorable sailing experience in downtown Toronto aboard a well-maintained 1997 Hunter 280. Perfect for small groups, this comfortable sailboat accommodates up to 6 guests, making it ideal for couples, families, or friends looking to explore the city from a unique perspective on the water.
Powered by a reliable 18 HP Yanmar diesel inboard engine, the boat offers smooth cruising at up to 6 knots, combining relaxed sailing with steady performance. Onboard, you’ll find everything you need for a comfortable and enjoyable trip, including an audio system, outside speakers, an ice box, and grill, perfect for creating your own atmosphere while cruising the waterfront.
Your captain, Domenic Grasso, brings experience in sailing tours, sunset trips, sightseeing, and canal boat experiences, ensuring a safe, relaxed, and enjoyable journey tailored to your group.
The boat is equipped with practical comforts such as a bathing platform, kitchen, one full bathroom with toilet, and ample space to relax and take in the stunning views of Toronto’s skyline and surrounding waters.
Included safety features such as GPS, VHF radio, anchor, and wheel steering provide peace of mind throughout your trip.
Guests are welcome to bring alcohol, children, and pets, and swimming is also allowed, making this a flexible and fun experience for all types of groups. Optional extras such as lunch can be arranged to enhance your time onboard.
Rates:
Monday–Thursday: $400 per couple or $100 per person (groups of 5–6)
Friday–Sunday & holidays: $500 per couple or $150 per person (groups of 5–6)
Whether you're celebrating a special occasion or simply looking to escape the city, this sailing trip offers a unique and unforgettable way to experience Toronto from the water. Book now and create lasting memories on the lake.

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Our sailing trip was awesome. Dom is super friendly, he showed us around the islands where we saw many types of birds and then we got to sail while watching the views. Definitely recommend!
Captain Domenic Grasso is a Toronto-based skipper who operates a Hunter 280 sailboat, offering relaxed and scenic cruises on Lake Ontario. He specializes in sailing tours, sunset adventures, sightseeing, and canal-style boat experiences, creating enjoyable and safe trips for small groups. With a focus on comfort and local knowledge, he provides an easygoing way to explore Toronto from the water.
Captain Domenic Grasso is a Toronto-based skipper who operates a Hunter 280 sailboat, offering relaxed and scenic cruises on Lake Ontario. He specializes in sailing tours, sunset adventures, sightseeing, and canal-style boat experiences, creating enjoyable and safe trips for small groups. With a focus on comfort and local knowledge, he provides an easygoing way to explore Toronto from the water.
Security deposit is not required
A refundable deposit is not required by the charter operator.
Fuel is included
Fuel is included in the price of the rental.
Free cancellation up to 1 day prior to trip
You can cancel or modify your booking up to 1 day before the trip date, free of charge. If you cancel or modify your booking later, or fail to show up, you'll forfeit 100% of what you've paid.
Reserve with a 10% booking deposit, pay the captain the rest
When the captain confirms your trip, BoatBooker charges your credit card a 10% booking deposit to guarantee your reservation.
The remaining balance is to be paid directly to the charter operator on or prior to your trip date in one of the following payment methods:
Cash
Bank transfer
