Top Canada Sailing Tours

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.

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.

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.

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.

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.

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.

Prebook your admission ticket to the Skylon Tower and soak up stunning views of Niagara Falls. A glass-enclosed elevator—‘Ride to the Top’—speeds you up to the observation decks in seconds. From your vantage point located 775 feet (236 meters) above the falls, snap photos of Horseshoe and American Falls, the Great Gorge, and Niagara River. The Revolving Dining Room and the Summit Suite Buffet offer sumptuous meal options. Visit at night to see the illuminated falls or check out the seasonal fireworks displays.

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.

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.

Soak in the sights along Halifax's coastline with this scenic sailing yacht tour. The small group size offers a more comfortable experience than crowded boat tours, while offering more savings than a private hire. Sit back and relax, or get some hands-on experience sailing with the crew if you're interested in trying it out for yourself.

Some Niagara Falls tours are American and some are Canadian. Not this one. Get the full experience from both sides of the border on this deluxe tour of everything Niagara Falls has to offer. Visit all the must-see Niagara Falls attractions, from the thrilling Maid of the Mist boat cruise to the exciting Cave of the Winds walk—even a trip to the top of the Skylon Tower and much more. All attraction and admission fees, plus hotel transfers and road tolls are included. Food and beverages are at your own expense.

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

Get to know Toronto’s Distillery District on this walking tour that’s easy on the wallet. A guide takes you around the Victorian Industrial architecture, sharing history and entertaining anecdotes along the way. Hear about business intrigue and the company that became the world's largest distillery.

Set sail on a 3-hour journey through the stunning St. Margarets Bay, blending sailing excitement with the beauty of Nova Scotia’s coastline. Departing from Shining Waters Marina, this adventure invites you to take the helm or simply soak in the fresh ocean air. Midway, anchor near scenic islands for a swim or exploration. Ideal for families and nature lovers seeking both adventure and relaxation, this immersive experience connects you to the water and the landscape. Enjoy personalized service and breathtaking views on a private charter for up to 12 guests. - 3-hour sailing adventure with island anchoring - Opportunities to explore, swim, or relax on deck - Suitable for families and nature enthusiasts - Private charters available for up to 12 guests

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 beauty of Nova Scotia’s South Shore with a JFarwell sailing experience in St. Margarets Bay. Just a short drive from Halifax, this coastal paradise is known for its rugged shoreline, scenic islands, and as home to the iconic Peggy’s Cove Lighthouse. This 2-hour sail is all about slowing down and soaking it in. You'll be greeted with a Nova Scotia crafted beverage as you step aboard your Beneteau Oceanis 45. Glide through the calm, sheltered waters of the bay as the sea breeze carries you past quiet coves and picturesque shoreline homes. It’s the perfect outing for families, couples, or anyone wanting a peaceful break surrounded by nature. - Duration: 2 hours with flexible sailing options - Depart from Shining Waters Marina, 25 minutes from Halifax - Ideal for all skill levels, no sailing experience needed - Private charters available for up to 12 guests

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.

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.

Immerse yourself in the beauty of the Salish Sea. Listen to seabirds as you take in breathtaking mountain vistas and island shorelines. Sea Lions are often seen, and sightings of Humpback Whales and Orcas are common in Georgia Strait. Relax and enjoy the sights, or take the helm for a hands on 3.5 hour sailing experience. 36ft Sunrise is fully equipped with safety gear and Quintin is a Transport Canada Certified Captain.

Set sail on a scenic journey through St. Margarets Bay, renowned for its rugged coastline and stunning islands. During this 2.5-hour Sunset Wine and Cheese sail, indulge in local wines and charcuterie as the sun sets over Nova Scotia's picturesque waters. This relaxing cruise offers the perfect backdrop for intimate gatherings or special occasions. Enjoy the calm evening breeze and take in the serene beauty of the bay while you unwind and embrace the coastal charm of Nova Scotia. - Duration: 2.5 hours, perfect for a delightful evening escape - Enjoy a curated selection of Nova Scotia wines and local charcuterie - Ideal for couples, special occasions, or a memorable night out - Private experiences available for up to 12 guests, ensuring intimacy and exclusivity

Explore Halifax Harbour like never before with a private sailing charter designed just for you. Whether you're looking to relax, celebrate a special occasion, or explore the coastline, each tour caters to your group's preferences. Enjoy visits to Fisherman's Cove, witness breathtaking coastal scenery, and keep an eye out for local wildlife during your sail. With options for various durations and itineraries, this experience offers a unique blend of leisure and adventure. Don’t miss out on creating unforgettable memories on the water in Halifax. - Private yacht exclusively for your group, accommodating up to 10 guests - Flexible routes and customizable itineraries for all occasions - Duration ranges from 2 to 5 hours, tailored to your preferences - Ideal for families, friends, visitors, and special events like proposals or birthdays

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.