Sailing in Downtown Toronto 

5.0/5 (1 review)
 36 Stadium Road, Toronto, ON M5V 3P4, Canada

Sailing in Downtown Toronto 

Toronto, ON, Canada
28 feet
6
5.0/5 (1 review)

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.

Domenic Grasso
Captain
Domenic Grasso
responds within an hour

Trip availability and prices

Trip Date:
Group Size:
Select date to see availability
September 2026
SuMoTuWeThFrSa
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Number of days
1
Group Size
2 adults • 0 children
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3 Hr – Midweek Sailing in Toronto
FREE Cancellation 1 day notice
3 hour trip starts at 5:00 PM
Seasonal trip
(Mon, Tue, Wed, Thu)
US $284
Private tour: up to 4 people
3 Hr – Weekend Sailing in Toronto
FREE Cancellation 1 day notice
3 hour trip starts at 5:00 PM
Seasonal trip
(Fri, Sat, Sun)
US $355
Private tour: up to 4 people

Customer reviews

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Rating

5.0
(1 review)
5.0
Boat & equipment
5.0
Captain & crew
5.0
Experience

All reviews (1)

Showing 11 of 1 review
Camille Rodriguez
Camille Rodriguez
us
Texas, US
Member since 2026
5.0
Verified
New
Great activity, great vibes, amazing views
3 Hr – Weekend Sailing in Toronto on September 5, 20264 adults

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!

FAQs about Sailing in Downtown Toronto

Sailing in Downtown Toronto offers the following trips to customers:
  • CA $400 per group, additional CA $100 per person after 4 guests - 3 Hr – Midweek Sailing in Toronto (3 hours)
  • CA $500 per group, additional CA $150 per person after 4 guests - 3 Hr – Weekend Sailing in Toronto (3 hours)
When you book a trip with Sailing in Downtown Toronto, you can expect the following amenities onboard:
  • GPS
  • VHF Radio
  • Anchor
  • Wheel Steering
  • Kitchen
  • Bathing Platform
  • Audio System
  • Outside Speakers
  • Ice Box
  • Grill
  • Galley Stove and Oven
Sailing in Downtown Toronto offers the following activities:
  • Sailing, Catamaran & Gulet Tours
  • Canal Boat Tours
  • Sunset Dinner Cruises

Your operator

Domenic Grasso
Domenic Grasso
Domenic Grasso

Toronto, Ontario, Canada

1 Customer reviews
Response time within an hour
Member since June 2026

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.

1 Customer reviews
Response time within an hour
Member since June 2026

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.

What the boat is like

Boat category
Other
Boat type
Sailing
Boat manufacturer
Hunter
Boat Model
280
Year built
1997
Boat length
28 ft
Capacity
6 persons
Engine model
Yanmar
Max crusing speed
6 knots
Powered by
1 x 18HP
Engine Type
Inboard
Fuel Type
Diesel
Number of cabins
2 cabins
Number of berths
2 berths
Number of heads
1 head
Number of full baths
1 full bath
Number of toilets
1 toilet
Boat category
Other
Boat type
Sailing
Boat manufacturer
Hunter
Boat Model
280
Year built
1997
Boat length
28 ft
Capacity
6 persons

Which kind of activities are offered

Sailing, Catamaran & Gulet Tours
Canal Boat Tours
Sunset & Dinner Cruise

Which amenities are available onboard

GPS
VHF Radio
Anchor
Wheel Steering
Kitchen
Bathing Platform
Audio System
Outside Speakers
Ice Box
Grill
Galley Stove and Oven

What's included in the trip price

What’s allowed on the boat

Child Friendly
Smoking
Alcohol
Pets
Swimming

What additional terms you should be aware of

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.

How cancellations work

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.

More details

How you can pay

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

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Sailing in Downtown Toronto
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5.0
/5
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US $284