Top Toronto Cruises & Sailing

Experience the best of Toronto with a Premier Dinner Cruise aboard the luxury vessel, Toronto Odyssey, and spend your evening in Toronto Harbor with dining, picturesque views, and DJ entertainment. While onboard, you’ll enjoy our chef-prepared plated menu, distinctive service, and breathtaking views of Toronto’s skyline from our climate-controlled deck. The Premier Dinner Cruise includes the selection of one salad, one main and one dessert. Sample salads; Garden Salad, Caesar Salad, Cream of leek and potato soup Sample entrées; Honey Sesame Chicken, Pan Seared Atlantic Salmon, Braised Beef Short Ribs and Vegetable Coconut Curry. Sample desserts; Chocolate Caramel Brownie, Country style carrot cake, Classic cheesecake and Fresh fruit plate Extras & Upgrades available onboard: - Cocktails, wine, and beer - Additional F&B upgrades (e.g. Roasted Garlic Shrimp, Atlantic Lobster Tail, AAA Beef Tenderloin) Additional Information: - We do our best to accommodate dietary restrictions

Relax on a 1-hour sightseeing cruise through Toronto’s scenic harbor and island parklands. Take in skyline views from a replica steamship while enjoying a narrated tour. Capture photos of highlights like the Toronto Islands, Island Airport, CN Tower, and the historic Gibraltar Point Lighthouse. It’s the perfect way to unwind and see the city from a fresh perspective.

Get a different perspective of the beautiful city of Toronto on this harbor front boat cruise. Set out from historic Pier 6 and look out at the glittering skyline, which includes the CN Tower, Rogers Center, and First Canadian Place. Pass by Toronto Island. Your captain provides entertaining narration along the way.

Enjoy a one-of-a-kind way to tour the Toronto Harbour on this tall-ship boat cruise. Hop aboard your vessel, a three-masted 1930s schooner, and set sail. Help the crew raise the sails or sit back and relax with on-board drinks and bites (additional expense). Enjoy panoramic views over Toronto’s islands and skyline—a view that few other visitors get to see—listen to sea shanties, and marvel as the ship’s cannon is fired.

Spend an afternoon enjoying brunch with stunning views of Toronto’s skyline. Enjoy a buffet with sweet and savory options as you sail along Toronto’s harbourfront, passing by landmarks like the CN Tower and Sugar Beach. The cruise offers a relaxing way to sightsee and enjoy the city’s beauty without dealing with crowds and traffic.

With Toronto situated on the edge of Lake Ontario, travelers have the opportunity to see the cityscape from a unique perspective. Head out to Toronto Harbour for a cruise around the bay on this onboard experience that includes a 3-course chef-prepared lunch to enjoy while you take in city views from the vessel’s climate-controlled deck.

Experience Canada’s Niagara Falls and Niagara-on-the-Lake on a full-day tour from Toronto with customizable options. Instead of planning your itinerary, you can simply opt in to the extra features you're interested in. Learn about Niagara Falls during the scenic drive from Toronto, and enjoy a trip to the Falls without the need to book accommodations for the night.

This cruise of the Toronto Harbour gives you the chance to enjoy scenic views of the Toronto skyline while enjoying a glass of prosecco. Enjoy incredible views of the city, island parklands, waterways and more! Your fully-licensed Captain will show you the sights including the Western Harbour Castle Hotel, The Lagoons and the Toronto Islands. On our way out into the harbour you can spot the Harbourfront Centre, CN Tower, Rogers Centre, Sugar Beach, the Redpath Sugar Refinery, and the historic Gibraltar Point Lighthouse. For an additional one hour other sites featured on this part can also include a tour of historic Hanlan’s Point, the Island Yacht Club, Toronto Island channels, and the woodlands of the Island Bird and Wildlife Sanctuary. Enjoy the scenery from the luxury of our rear outdoor seating area or relax and sunbathe on the front deck of the 44 feet cruiser yacht!

Step aboard our private Single-Floor Yacht and enjoy a one-of-a-kind cruise through Toronto Harbour with breathtaking skyline views. Unlike crowded public tours, this experience offers exclusivity, comfort, and personal service—making it ideal for couples, families, or small groups looking for a more intimate way to enjoy the city from the water.

A shared sailing experience is a cost-effective and hassle-free alternative to hiring your own boat. No experience is required, as a captain takes the lead as you embark on a scenic journey to see views of Humber Bay, Lake Ontario, the Eastern Gap, and beaches along the Toronto shoreline. During the trip, you can either sit back and enjoy the views, or participate and get some sailing tuition from the captain.

Escape the city and explore Algonquin Provincial Park on a full-day trip from Toronto. Enjoy scenic lookouts, an easy guided hike, the Visitor Centre, wildlife viewing, and breathtaking Canadian landscapes. Experience one of Ontario's most beautiful natural destinations in every season. Famous for its forests, lakes, and wildlife, Algonquin is a paradise for nature lovers and photographers. You may spot moose, loons, beavers, and other native species while discovering why it's one of the top day trips from Toronto.

This cruise of the Toronto Harbour gives you the chance to enjoy scenic views of the Toronto skyline while enjoying a glass of prosecco. Enjoy incredible views of the city, island parklands, waterways and more! Your fully-licensed Captain will show you the sights including the Western Harbour Castle Hotel, The Lagoons and the Toronto Islands. On our way out into the harbour you can spot the Harbourfront Centre, CN Tower, Rogers Centre, Sugar Beach, the Redpath Sugar Refinery, and the historic Gibraltar Point Lighthouse. For an additional one hour other sites featured on this part can also include a tour of historic Hanlan’s Point, the Island Yacht Club, Toronto Island channels, and the woodlands of the Island Bird and Wildlife Sanctuary. Enjoy the scenery from the luxury of our rear outdoor seating area or relax and sunbathe on the front deck of the 44 feet cruiser yacht!

Experience the spectacular Niagara Falls on a day trip from Toronto, spending the day exploring the region's scenery, history, and varied attractions. This fun, flexible tour combines independent time at Niagara Falls with an optional in-season boat tour and Journey Behind the Falls experience. With pickup and drop-off at select downtown Toronto hotels and locations, enjoy a seamless day out at the natural wonder.

See the best of Toronto in just half a day—and let someone else handle the logistics—on this hassle-free, guided tour. With hotel transfers, admission tickets, and a (seasonal) harbor cruise included, getting around is made easy. Visit historical highlights such as Queen’s Park, Old City Hall, and St. Lawrence Market, and even ascend to the top of the CN Tower for city panoramas that are hard to beat.

Take in sweeping aerial views of Toronto from the comfort of an 8-person executive plane. Don’t forget your camera: The pilot’s flight path is designed to showcase top landmarks such as the CN Tower, Rogers Center, Toronto Islands, and Lake Ontario. For your comfort and convenience, the experience includes access to the airport’s VIP lounge prior to departure.

Explore Toronto's rich heritage and vibrant neighborhoods on a private three-hour walking tour with expert guide David B. (Dave). Drawing from his experience in urban affairs, navigate through key historical sites and immerse yourself in the city’s multicultural atmosphere. Visit iconic landmarks like St. Lawrence Market and the Distillery District while discovering hidden gems in Kensington Market and Chinatown. Gain insights into Toronto's evolution, architecture, and public spaces, tailored to your interests for a personalized experience. - Private three-hour tour led by a knowledgeable urban design expert - Explore diverse neighborhoods including Kensington Market and Chinatown - Visit historical landmarks like Old City Hall and the waterfront - Flexible pace with opportunities for photos, snacks, and local shopping

Toronto has so many landmarks to explore that it can be tough to know how to fit everything you want to see into one trip. Thankfully, this half-day small-group walking tour takes you to a curated selection of the city’s most popular sights. Walk the Hockey Hall of Fame, pass by the historic Union Station, gaze up at the lofty CN Tower, and much more.

Departing from the central waterfront, Obsession III offers spectacular dinner cruises to fit any occasion. Whether you’re new in town or a native Torontonian, whether you’re celebrating a first date, birthday, anniversary or a night out with friends, we offer the perfect location. Enjoy a contemporary sit down dinner with an assortment of appetizers, followed by your choice of salads and entrees. Be sure to save room for our delicious dessert selection to round off your meal! Throughout dinner, our on board DJ will be playing background music and will transition later in the evening to dancing the night away with a DJ, classic and current hits.

Discover the thrill of Niagara Falls during this full-day trip from Toronto, limited to just 15 people. Watch and hear the thundering falls aboard the popular Hornblower cruise. Stroll the Niagara on the Lake Heritage District, and check out the designs on the Floral Clock, all in just one packed day.

Simplify your departure from Toronto with an easy private transfer from your accommodation to Pearson Airport. There’s no need to haul your luggage onto public transport or drive all around the city picking up strangers. Your driver will pick you up from your lobby and transport you directly to the airport in good time for your flight. Arrive feeling calm and ready for your onward journey.

Experience the Canadian side of Niagara Falls from all angles—above, under, and behind the falls—in one action-packed morning or afternoon tour. Enjoy the popular Journey Behind the Falls experience, zip up to the top of the Skylon Tower for a panoramic view over the falls, then set sail on a thrilling boat ride (May–December) beneath Horseshoe Falls.

Experience Niagara Falls by day and night on this small-group day tour. A driving tour of the area helps you get your bearings. Then, see the Falls from three different angles: from above at Skylon Tower, up close aboard a cruise, and the Journey Behind the Falls. Relax after a day of sightseeing with dinner at a restaurant offering dramatic views of Horseshoe Falls lit up.

One ticket gets you entrance to more than 100 surreal and reality-bending rooms in Toronto’s Museum of Illusion. From holograms to vortex tunnels, game rooms to 3D puzzles, and much more, the Museum of Illusion has plenty of exhibits that promise a full day of fun for kids, teens, and adults alike. Choose a time that works best for you, secure your tickets in advance, and then explore all at your own pace.