Toronto’s location on the northwestern shore of Lake Ontario makes it a prime spot for sailing adventures. With its bustling harbor, towering skyline, and nearby islands, Toronto offers a variety of memorable water-based experiences. Whether you’re after a laid-back daytime cruise, a romantic sunset sail, or an exclusive private charter, the options are plentiful. We particularly like the 2-hour Shared Sailing Experience for its friendly atmosphere and stunning views, including the iconic CN Tower, and the Luxury Yacht Prosecco Cruise for a quick but indulgent cityscape tour. Each experience offers something unique, making Toronto an ideal city for both casual sailors and those seeking a more luxurious outing.
Toronto is especially great for sailing because of its accessible waterfront, the scenic Toronto Islands, and the modern skyline that’s best viewed from the water. Whether you want to learn how to sail, enjoy a romantic hour on a private yacht, or just relax with a glass of Prosecco while taking in the city views, there’s a tour for you. The city’s waterways are safe, well-regulated, and full of interesting sights, from historic landmarks to natural scenery. Plus, many tours require no prior sailing experience, so you can enjoy the ride even if you’re new to boating.
1. 2hr Shared Sailing Experience in Toronto
At number one, this shared sailing experience offers a fantastic way to enjoy Toronto’s waters without the expense or hassle of renting your own boat. No experience is necessary—your captain handles the sailing while you sit back, relax, or participate in steering if you wish. Over roughly two hours, you’ll cruise past Humber Bay, Lake Ontario, the Eastern Gap, and beaches along the shoreline, with a small group that ensures personalized attention. The boat is equipped with comfy onboard beanbags, and you’ll get excellent views of the CN Tower and Toronto skyline.
Made for those who prefer a relaxed, social atmosphere, this tour is praised for its friendly crew and beautiful scenery. Reviewers often highlight the professionalism of Captain Rob and his helper, and many mention how peaceful and scenic the ride is, especially with blankets and optional prosecco for sale. It’s perfect if you want a hassle-free way to see Toronto from the water without needing any sailing skills. The value for the price — around $140.10 per person — is excellent for a small-group experience with memorable views.
Bottom line: If you want a relaxing, no-stress introduction to sailing on Lake Ontario, this tour is hard to beat for its intimate setting and spectacular city views.
2. 60-Minute Toronto Luxury Yacht Sightseeing Prosecco Cruise!
Number two on our list is the luxury yacht cruise that combines sightseeing with a glass of prosecco. For about an hour, you’ll cruise around Toronto Harbour, passing landmarks like the Harbourfront Centre, Rogers Centre, and the Toronto Islands, all while enjoying the city’s skyline and waterways. The boat departs from a private dock in downtown Toronto, making it easy to hop aboard.
This cruise stands out for its elegant setting and the opportunity to sip prosecco as you take in the views. The captain, fully licensed, shares insights about Toronto’s harbor and cityscape, making it both a visual treat and an informative experience. Reviewers love the spaciousness of the boat and describe the experience as romantic and relaxing, with many noting it’s one of the best things they did in Toronto. The ticket price of around $107.64 per person offers very good value for a short luxury cruise in the city.
Bottom line: Ideal for couples or small groups wanting a classy, scenic tour with a beverage, this cruise packs a lot into a short trip, perfect for a quick taste of Toronto’s waterfront.
3. 3hr Shared Sailing Adventure
Number three is the 3-hour shared sailing adventure, which is a longer, more immersive experience. Departing daily from May to September, this tour takes you around Toronto’s islands on a yacht, allowing plenty of time to relax or try your hand at steering. The trip includes views of Sugar Beach, Gibraltar Point Lighthouse, and the Toronto skyline from the calm waters of Lake Ontario.
This tour earns high praise for its personalized attention and the chance to really unwind. The crew creates a friendly atmosphere, and the experience is suitable for anyone looking for a peaceful, scenic day on the water. The cost of about $177.42 per person is reasonable considering the extended duration and small-group setting. Guests love the opportunity to sit on deck beanbags and enjoy the natural beauty of Toronto’s waterfront away from crowded land-based spots.
Bottom line: For those wanting a longer, relaxed sailing day with options to steer or just soak in the views, this adventure is a top choice.
4. Toronto: Sailing Yacht Cruise of Toronto Harbor and Islands
Number four offers a flexible sailing cruise, available in 2, 3-hour day sails, or a 2-hour sunset trip, aboard a luxury 41′ yacht. The variety allows you to choose the perfect time—whether you want to see the city in daylight or enjoy a sunset. The yacht’s size and amenities provide a comfortable ride, and the captain and crew focus on delivering a smooth sailing experience.
Guests often mention feeling the breeze and enjoying Toronto’s skyline from the water, with some opting for sunset sails to experience the city’s lights. The tour is perfect for those who like a flexible schedule or want to indulge in the luxe side of Toronto boating. The price of $136 per person balances comfort and value, making it a versatile option.
Bottom line: This flexible tour is great for groups who want options and a comfortable, private yacht experience with stunning views.
5. Toronto: Private Luxury Yacht Sightseeing Cruise & Prosecco
Number five provides a private luxury yacht cruise, perfect for romantic outings, small celebrations, or special occasions. With just your group aboard, the focus is on comfort and exclusivity. The cruise features views of the Toronto skyline, Toronto Islands, and Gibraltar Point Lighthouse, with a glass of prosecco included.
The fully licensed captain will show you the city’s most famous sights, and you can relax on the deck or in the rear seating area. The price of about $108 per person for an hour offers good value for privacy and tailored service. Reviewers appreciate the attentive crew and the chance to enjoy the Toronto waterfront without the crowds.
Bottom line: Ideal for couples or small groups seeking a private, intimate experience with a scenic backdrop and a touch of luxury.
6. 90-Minute Toronto Luxury Yacht Sightseeing Prosecco Cruise
Number six is a slightly longer 90-minute cruise, combining the scenic Toronto skyline with a glass of prosecco. This trip explores the Toronto Harbour and the Toronto Islands, including views of Hanlan’s Point Beach, with a final return to the harbor. It’s perfect if you want a quick, upscale experience with a little more time than the one-hour cruise.
Guests highlight the beautiful boat and the captain, who shares insights about the sights. The experience is well-suited for those wanting a short but luxurious escape on the water. At $141.46 per person, it offers a premium feel for a relatively brief trip.
Bottom line: For a short, elegant cruise with a touch of bubbly, this is an excellent pick.
$141.46 per person
7. VIP Luxury Yacht Charter for up to 12 Guests
Number seven is the VIP yacht charter, offering four hours of exclusive access to Lake Ontario. Perfect for celebrating a special event, it includes a trip to Hanlan’s Point Beach with a barbecue, along with sailing among the Toronto Islands. The boat can hold up to 16 people, giving plenty of space for friends or family.
Guests love the flexibility and social vibe, with reviews noting the staff’s friendliness. The price of about $1,633 per group makes this a worthwhile splurge for those wanting privacy and all-day fun. The itinerary includes stops for water sports and relaxing in the harbor.
Bottom line: If you’re planning a celebration or a group outing, this charter offers the most privacy and flexibility, with a mix of sailing, swimming, and socializing.
8. Yacht Proposal Package with decoration and Prosecco
Number eight is a special occasion yacht proposal, decorated with a “MARRY ME” sign and balloons. Over two hours, you’ll enjoy a scenic cruise with a glass of prosecco, perfect for proposals or romantic celebrations. The yacht departs from downtown Toronto, with views of the skyline and Toronto Islands.
While reviews mention the decor and romantic setting, some note that the price is high for the experience—around $1,073 for up to 12 people. This tour suits couples or small groups celebrating a milestone and wanting a memorable, personalized touch. It offers a scenic, intimate backdrop to a special moment.
Bottom line: Best for romantic occasions and special celebrations, but be aware of the premium price.
$1,073.01 per group (up to 12)
9. Luxurious 40ft Yacht Charter
Number nine features a 40-foot yacht charter, ideal for groups up to 17 people. While reviews are not provided, the focus is on a relaxed, enjoyable experience with optional add-ons and discounts for larger bookings. It’s a budget-friendly way to enjoy a private yacht cruise with friends or family.
The boat’s size and amenities aim to ensure comfort and fun, making it suitable for casual celebrations or day trips. With no reviews, it’s more about the value and flexibility than detailed feedback, but the overall concept suggests a straightforward, enjoyable outing.
Bottom line: For those after a flexible, affordable private yacht experience, this is a solid option.
$540 per group up to 17
10. Private Sailing in Downtown Toronto
Number ten is a personal sailboat experience that offers a private cruise around the Toronto Islands. The host is your own captain, providing a customizable, intimate experience with great views of the skyline. Perfect for romantic outings or small groups looking to sail with a personal touch.
This experience stands out because of its personalized approach, allowing you to take photos of the skyline and enjoy the water at your own pace. Its price of $83 per person makes it accessible for those seeking a private, relaxed sailing adventure in the heart of Toronto.
Bottom line: Excellent for couples or small groups wanting a tailored, romantic water experience with the flexibility of a private boat.
$83 per person
11. Sailing in the Harbour – Hands-on Toronto Sailing Experience
Number eleven offers a hands-on sailing experience with a local guide. You’ll learn sailing basics and try steering the boat yourself during the trip around the Toronto Islands. The tour’s small group size (max 8 people) means plenty of personalized attention.
This experience is ideal if you want to actively participate rather than just watch. You’ll see the Toronto skyline from the water and learn skills that might even inspire you to take up sailing yourself someday. It costs around $90 per person, offering a good balance of learning and scenic fun.
Bottom line: Perfect for those curious about sailing and wanting an active, hands-on experience in Toronto’s waters.
$90 per person
How to Choose the Right Sailing Experience
When selecting a sailing tour, consider your budget, time availability, and what kind of experience you want. For short, scenic trips with a glass of Prosecco, the 60-minute luxury yacht or the 90-minute cruise are excellent options. If you’re craving a longer, more immersive ride with the chance to learn sailing, the 3-hour shared adventure or the full-day private charter fits the bill. Budget-conscious travelers might prefer the private sailing in downtown Toronto, while special occasions call for the luxury yacht proposal or VIP charter.
Booking early is advised, especially in peak summer months, to secure your preferred time and experience. Also, check whether you want a relaxing sightseeing cruise, a learning experience, or a private celebration to guide your choice.
Final Thoughts
From quick, champagne-infused harbor cruises to extended sailing adventures on Lake Ontario, Toronto’s sailing experiences cater to many tastes. If you’re after a romantic escape, the luxury yacht cruises are perfect. Those seeking a more active, participatory outing might enjoy the hands-on sailing experience. And if you’re traveling on a budget but still want a memorable trip, the shared day sail offers great value.
Whatever your choice, Toronto’s waterways promise stunning views, memorable moments, and plenty of opportunities to enjoy the city from a different perspective. Be sure to book early, especially for the most popular tours, and prepare for a splash of adventure on Lake Ontario.