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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

Avoid the stress of navigating Toronto on your own aboard a hop-on hop-off bus. Choose from 24- or 48-hour options to suit your schedule. Listen to audio commentary as you stop at popular destinations such as Casa Loma and the Distillery District. Take in scenic views from the top of a double-decker bus, or shelter from the sun or cold inside the bus.

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.

Enjoy an unforgettable night at Niagara Falls on this small-group evening tour. Savor a 3-course dinner at a restaurant with views of the thundering falls lit up in vivid hues. Then, hop on a Niagara Falls cruise and watch a fireworks show over the water. Finally, head to Illumination Tower and enjoy the chance to control the color of the lights over the falls.

Discover one of the world’s most famous waterfalls on this Niagara Falls day tour from Toronto. Take a scenic drive along the Niagara Parkway with your guide. Admire top regional attractions such as the floral clock. Enjoy numerous photo stops including the Niagara Whirlpool and the Niagara River viewpoint. Spend about three hours exploring the Niagara Falls site and marvel at the swirling, surging flow.

Enjoy a relaxing three-hour yacht cruise around Toronto’s islands in Lake Ontario, admiring the city views along the way. You can choose to sit back and relax on the beanbags on deck, or to take the helm and have a go at steering the yacht yourself. This is a small-group activity so you can enjoy the peace and quiet out on the lake.

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

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.

Experience Niagara Falls from land and air on this small-group tour. Fly over the falls on a helicopter ride; get close to them on the seasonal boat tour; and feel the power on the Journey Behind the Falls walk. Round-trip hotel pickup in Niagara Falls, Ontario is included for a seamless experience.