Our voyages take you along gorgeous coastlines and we offer just as much onshore. Once Caledonia arrives in port, your options are endless: saunter off and explore a new landscape, hike up to breathtaking lookout points, navigate local waters on one of our kayaks, or even hop on a bike for an afternoon adventure.

Whether you're sailing solo, looking for a romantic getaway on the sea or a unique family vacation, Canadian Sailing Expeditions and our crew will make it happen. Through flexible itineraries and extensive travel partnerships, we can accommodate groups of all ages and guests of all interests. With Canadian Sailing Expeditions, you’ll witness towering cliffs and picturesque shorelines from a completely different point of view. Once in port, the choices are all yours. Cycling through charming waterfront villages, kayaking across spectacular bays, discovering local culture and cuisine and appreciating spectacular scenery and wildlife from up close. The bottom line? If you’re looking to get away, you’ve found the right place.

With Canadian Sailing Expeditions, you’ll go as far beyond the ordinary as you wish. We offer you the Caribbean and coastal Canada. The choices are all yours!

Our Company
Founded in 2000, Canadian Sailing Expeditions is led by a group of professionals who combine over 35 years of experience in the marine industry as owners and operators of traditional tall ships. By sharing their passion for exploring, Doug Prothero, David Evans and Michelle Clark give people a chance to rediscover themselves while exploring the lore and beauty of our seacoast. From family getaways to personal journeys, we make adventure accessible.


Our Culture
Along with our diverse voyages – like coastal cruising, sail training, daysails and corporate charters – we provide an equally memorable experience through the friendliness and spontaneity of our crew. The very nature of a sailing adventure requires a certain flexibility, and our staff has a reputation for adjusting on-the-fly to accommodate guests. Sometimes this involves an extra day in port or even bringing local chefs on board for an impromptu dining experience. Whatever we can do to enrich your voyage, we’ll happily do it.

Canadian Sailing Expeditions embraces diversity and excellence. We pride ourselves in offering experiences where all individuals are valued and respected.