Discover the Magic of Sailing: Private Tours for Every Occasion

Experience Toronto from a new perspective with a private day sailing charter. Enjoy the stunning views of the city's downtown skyline, providing the perfect backdrop for a striking photo. Whether you're seeking a romantic cruise for two, a fun-filled boating adventure with family and friends, or a unique setting for your corporate event, birthday or bachelor/ette party, a day sailing charter is the perfect way to explore Lake Ontario and its surroundings. With a private sailboat and one of our experienced, Sail Canada certified captains, you can sit back and relax, taking in the sights and sounds of the harbor. Alternatively, you can take a turn at the helm, help with trimming the sails, or simply enjoy the view. Our captains are happy to provide an introduction to sailing, making this trip perfect for beginners and first-time sailors. A private sailboat charter is the perfect setting for special occasions and weekend getaways. We prioritize your safety and comfort to ensure that your sailing trip is enjoyable, memorable, and worry-free. Available day tours: Friends & Family Wine & cheese Photo shoots Sunset sailing Toronto Island adventure Canada Day fireworks International Air Show Introduction to sailing Mileage builder $100 per person (Mon - Thurs). $150 per person (Fri - Sun & Holidays). Max: 5 people. Sail Canada certified, insured, licensed and registered with Transport Canada. If you have any questions just hit “Send Inquiry” and send a custom offer!