Top Canada Sailing Tours

Soak up coastline views at the most scenic time of day on this small-group sunset cruise out of Halifax Harbour. Sail down the narrows of the Northwest Arm past George's and McNabs Islands as the sun sets over beautiful homes. Toast the experience with four included Nova Scotian wines—sparkling, Tidal Bay, rose, and red—paired with local cheese boards during a guided tasting.

Take a sailing trip out into the Howe Sound with this small-group sailing experience. Your captain will meet you and your fellow passengers in Squamish, about a 40-minute drive north of Vancouver. You'll then set sail out into the Howe Sound, where you'll have the opportunity to try your hand at sailing yourself. You may even spot whales or dolphins.

Enjoy spectacular waterfront views—and even help hoist the sails—as you take a ride on the Tall Ship Silva along the scenic Halifax Harbour. This schooner gives passengers the opportunity to join the crew in manning the sails, tying knots, or even taking a turn at the helm. If you prefer, you can sit and watch the action while admiring many of the region's top landmarks from the water's edge.

Set sail for a tranquil evening on Howe Sound with our enchanting afternoon sailing experience! Our certified instructors are dedicated to providing a safe, comfortable, and unforgettable outing. Guests are welcome to be as hands-on as they like, from learning the ropes to simply relaxing and enjoying the breathtaking scenery. Our sailing experiences take place aboard our exquisite 2007 49ft Beneteau sailboat which is renowned for it's comfort, performance, and elegant design Our spacious layout provides ample room for guests to relax and enjoy the journey in style. The Beneteau has generous deck space, with plenty of room to stretch out, or even gets hands on with the sails! Below deck, you’ll find a bright and airy salon. The Beneteau 49 is celebrated for its stable and responsive handling, making for a smooth and enjoyable ride. After your adventure, guests are welcome to enjoy our beautiful waterfront property equipped with a BBQ, hot showers and a Jacuzzi hot tub.

Experience gold and pink-hued skies while escaping the hustle and bustle of the city on this sunset harbor cruise. Take in the views from the upper deck, snap photos of the city from a vantage point most travelers don’t get the chance to see, and relax on board with optionally purchasable wines, beers, and cocktails.

Let the power of mother nature propel you as you cruise across the harbor on Halifax's only wind-powered sailing experience. This small-group tour is a great introduction to sailing: you can be as hands-on with the sailing process as you like, or simply sit back and enjoy the scenery.

Go sailing in Halifax with this small-group tour designed for families. Meet your captain for a morning sail on a 45-foot yacht to experience a wind-powered adventure. Learn new sailing skills and set out along the coastline. Kids can earn an official crew member certificate during the excursion.

Spend a day immersed in Kelowna’s beautiful nature as you embark on a sailing cruise on Okanagan Lake. For this adventure, board your private vessel and enjoy a few hours of relaxation, letting the wind guide your boat across the lake. Sail past key landmarks including downtown Kelowna, City Park, Hot Sands Beach, and the Floating Bridge.

Escape to the open waters of Vancouver on a sailing adventure that offers the best of the city’s scenic vistas. This 2.5-3 hour sailing experience takes you through the picturesque False Creek and English Bay, where you’ll be able to take in the views of the city skyline, mountains, and waterfront landmarks. This is more than just a sightseeing cruise — it’s an authentic West Coast sailing experience led by someone who’s truly at home on the water and teaches you the ropes. If you’re an adventurer at heart, this sailing journey blends discovery with relaxation, entertainment, and flavours. With a little luck, we may even sight the Dall's porpoise or a pod of Orcas! - Exclusive sailing experience with a maximum of six guests - Engage with a knowledgeable skipper sharing local history and tales - Opportunity to see marine wildlife

This two-hour sail allows you to soak in the sights along the coastline so close to our urban center! Pass by landmarks such as George's Island, Pier 21, Point Pleasant Park, and more. This laid-back sail is designed for you to enjoy maximum relaxation, and leave the work to our crew. If you'd like to be involved in the sailing, we would love the opportunity to show you the ropes! After being greeted with a custom local cocktail (or mocktail!) upon arrival, you can choose to explore the sailing yacht, take in the sights, or try your hand at the helm.

Get a new perspective on Vancouver by getting out onto the water. This small-group boat tour takes you sailing around the city and its harbor aboard a 50-foot Jeanneau sailboat departing from North Vancouver. Relax with an included drink and snack as you take in the views of Coal Harbour, Stanley Park, Passage and Bowen Islands, Point Atkinson, Howe Sound, and more.

Discover the sights and sounds of Halifax as you sail along its coast on a moonlight cruise. Join a small group and board your yacht, taking in the illuminated skyline while you sail. Enjoy a relaxed evening with your friends and family paired with good music and some of Nova Scotia’s best craft beer, wine, and spirits (for purchase).

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.

Set sail on the tranquil waters of the Saint John River aboard our O'Day 34 sailing yacht, for a 2.5 to 3-hour introduction to boating experience. Led by a certified Sail Canada instructor, this cruise offers first-time boaters a unique opportunity to learn the basics in a comfortable environment. Whether you are completely new to sailing or have some experience, the session is tailored to meet your needs and enhance your confidence on the water. Enjoy the serene surroundings as you navigate through basic sailing techniques on this memorable outing. The cruise is for up to 6 people, so there is a chance of sharing the experience with others.

If you've always wanted to try sailing, get your sea legs on a small-group sailing adventure on Vancouver Island. Learn sailing essentials from an experienced skipper, and then put your new skills into practice while navigating the Strait of Juan de Fuca. With wind in your sails, look for wild marine life including humpback whales, orcas, sea lions, and dolphins.

We provide a memorable 3 hour sailing adventure, on our safe, comfortable Hunter 35.5 yacht, which may include possible sightings of orca whales, eagles, seals, and porpoises. Guests are welcome to help as much or as little as they want sailing the boat, or just relaxing! Optional stop at Sidney Spit Marine Park by prior arrangement.

Make the most of British Columbia’s natural beauty by exploring Okanagan Lake from Naramata. Craft your ideal experience–your activity level and how involved you’d like to be as you set sail aboard a yacht are up to you. Relax on board, go for a swim, or try paddle boarding in the water.

Discover the power, beauty, and thrills of Niagara Falls in one seamless 5 hour tour. Drive past scenic gems like Dufferin Islands and the International Control Dam, then get up close behind the Falls at Journey Behind the Falls and Table Rock. Snap photos at the seasonal Floral Clock, soar over swirling rapids in the Whirlpool Aero Car, and cap it off with an exhilarating boat ride right at the base of the Falls. This is more than a tour—it’s a full-day adventure combining iconic views, thrilling experiences, and unforgettable memories. Perfect for first-timers or those short on time, it’s your ultimate Niagara experience. Book now to secure your spot and make memories you’ll never forget!

Go sailing at sunset in Halifax with this private yacht tour complete with wine and cheese. Climb aboard a boat for a scenic tour that includes a tasting of four Nova Scotia wines plus cheese and snacks. Set sail into the Northwest Arm to see local landmarks including the Dingle Tower and lush parks. Plan a romantic evening in Halifax with this private boat cruise and customize the itinerary if you wish.

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.

Your private sailing charter will offer you a unique and scenic perspective of Vancouver Harbour and its surrounding inlets. Contagious is an Oceanis 46.1 and has all the features of a large cruising Yacht with a rare balance between elegance, usable space and performance. Contagious is easy to sail and pleasantly comfortable.