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Sail in downtown Toronto

With Captain

100% refund within 24 hours of your trip

5.0(28 reviews) ·

40 bookings

Canada,Ontario,Toronto,Sailing

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This date is available.

Unwind on a relaxed cruise or turn up the music for a livelier outing, with skyline views, island scenery, and an easygoing, welcoming atmosphere.

Clean, comfortable powerboat with onboard bathroom, BBQ, and Bluetooth speakers, giving you an easy setup for music, snacks, and relaxed time on the water.

Guests praise the captain as warm, patient, and flexible, sharing local stories, teaching beginners, offering photos and options to tailor the route to your group.

Renters say this listing is great for:

Family TimeParty/EntertainmentSightseeingPhotography

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AI Overview

Owner's Description

Sit back, relax and enjoy a peaceful boat ride around the Toronto Islands *OR* crank up the music and have a blast. BBQ and bathroom available onboard. Bluetooth speakers provided. Bring your own alcohol and snacks. Dog's welcome! I'm happy to accommodate special requests such as getting up close to the CN Tower for pictures, sailing lessons, or stopping at the beach for a BBQ and a swim. Pricing for 3 hour sail (1 or 2 hour sails are the same price): Monday to Thursday Pricing : 1-4 People: $450 5 People: $550 6 People (max) : $650 Friday, Saturday, Sunday (and Holidays) Pricing: 1-3 People: $550 4-6 People: $150 per person If the weather is bad, feel free to cancel the day of the sail for a full refund. Commercially insured, licensed, certified, and registered with Transport Canada.

Dom

40 total bookings

Capacity: 6 guests

Sailing: Sail

Reviews

5.0 (28 reviews)

Listing Accuracy
Awesome
Departure & Return
Awesome
Vessel & Equipment
Awesome
Communication
Awesome
Value
Awesome
Itinerary & Experience
Awesome

67 photos have been added by reviewers who booked this listing.

HD
Harry

Dom was amazing he takes great pictures was Betty accommodating and gave us lots of fun facts! Was a beautiful experience overall!
GK
Galina

Dom is a great and hospitable captain. He was very kind, he offered drinks, always checked with what we would like to see and was ready to offer alternatives. I would highly recommend his services!
AB
Alan

Dom was a great host. He went above and beyond. We have nothing but good things to say about our experience. Ot was a great experience and we would definitely recommend it for anyone visiting the area or locals just wanting to get out on the water and enjoy the beautiful views.
KD
Katherine

We had an amazing time sailing with Dom! The views of the Toronto skyline were incredible, and we learned so much about the Toronto Islands and about sailing along the way. What we especially appreciated was Dom’s ability to make sailing feel accessible and unintimidating—he cuts through the insider language and conventions and focuses on the practical knowledge that really matters when you’re getting started. It made sailing feel much more approachable and feasible for complete beginners like us. Dom was an incredibly warm and welcoming host, and the whole experience was relaxed, fun, and genuinely informative. We also loved how easy it was to bring our own snacks and drinks. Highly recommend!
Rudi

Dom is a great sailor. Very willing to teach. Very open for any suggestions. We had a great experience with him.