American Sailing Association
Passage Offshore is an American Sailing Association certified sailing school with courses offered in some of the most unique sailing destinations in the world. This 6 to 9 day course teaches you the true art of sailing and connects you with adventures that motivate us to explore.
Course Certifications
Basic Keelboat 101
Coastal Cruising 103
Bareboat Charter 104
Coastal Navigation 105
Captain
Dwyer grew up in the mountains of New Hampshire and spent a good portion of his childhood in the backcountry. After a stint building a ski factory in Asia, Dwyer quit his job, bought a sailboat, learned to sail over the course of a couple months, and sailed single-handed 12,000 nm down the west coast of the Americas to Chilean Patagonia. Dwyer draws his culinary inspirations from his travels and his time around the campfire. He has a soft spot in his heart for dumplings (of all shapes and sizes) and he once cooked a three course meal over a volcanic vent during a ski tour high in the Andes. He's committed to lowering his environmental footprint and focuses on adapting his cooking to whatever ingredients are local and seasonal.
Captain
Born and raised in Key West, FL, Capt. Lilly has lived her life surrounded by saltwater. With over 20 years of boating experience, Lilly learned to operate her own boat - navigating it through the narrow channels and over the shallow waters of the Florida Keys backcountry years before she could drive a car. At 15 she sailed from Key West to Boston. Lilly is an avid angler and free diver, loves to surf, hike, and explore the many gifts Hawaii has to offer. In her lifetime of experience on the water Lilly has matured into a skilled boat handler with an emphasis on the safety of her crew and passengers, and a gift for sharing her love of the ocean. After graduating from the University of Florida, Lilly moved aboard a 125-ft gaff-rigged schooner that she crewed seasonally from Key West to Boston. In the Caribbean, Lilly worked with a fleet of boats including large catamarans and schooners. She has managed the fractional ownership business SailTime and the American Sailing Association School in Virginia Beach, where she maintained, operated, and taught sailing aboard a fleet of boats. She currently holds a 100-ton GRT Master Captains License with Sail and Tow endorsements and her teaching certification through the American Sailing Association.
Founder, Captain, & Broker
Captain Armstrong founded the Sailing Collective with a passion for connecting people with the world through adventures and sailing. Having been raised with values based on multi-cultural awareness and the importance of global culture, Armstrong combined his enthusiasm for sailing and exploration to create an intergrated sailing vacation organization open to adventuers, explorers, and sailors alike. In addition to founding the Sailing Collective Travel Co, Armstrong is the co-autor of Sailing the Seas. He is also a trained musician having graduated from music conservitory in New York City and holds a graduate degree in Economics. Captain Armstrong is also wildly passionate about food and wine, which is very evident to anyone joining him on a Sailing Collective voyage.
Captain
Janet grew up in Maryland and in the Adirondacks of NY where she developed her love to sail. In college, she was named All-American in lacrosse and also played soccer while earning her Psychology degree. Post graduation she moved to Key West, Fl where she began her career working as a sailor. She enjoys spending time with her black lab mix “Brewer”, performing comedy at the local comedy club, and traveling. She has recently acquired her EMT certification nationally and in the state of NY where she hopes to work as an EMT/firefighter in the future.
Captain
Hailing from the not-at-all-coastal town of Bordertown, South Australia, Jack grew a healthy obsession with BMX riding at a young age. His sailing started when his cousin Riley invited him to help sail a boat he had just bought called La Vagabonde. La Vagabonde happened to be moored a few boats away from Libertas (captained by James) in Cape Verde as both boats prepared to cross the Atlantic. They all caught up again on the other side, with both crews literally running into each other in Road Town, BVI. La Vagabonde has since become a Youtube sensation, with over 300K subscribers, and Libertas is the flagship of Sailing Virgins fleet. Following the second meetup, James and Jack spent several weeks in the Caribbean sailing together. Jack subsequently worked several European and Caribbean seasons with The Yacht Week as skipper, lead skipper and ultimately Route Manager, as well as some transats under his belt. Jack holds his Yachtmaster Instructor certificate from the Royal Yachting Association and loves to teach catamaran hacks.
Captain
Jamie grew up just outside landlocked London although this didn't stop him from finding his way to the water. He started racing dinghies at eight years old and turned his hobby into a job at thirteen as a sailing instructor throughout his youth. whilst at university studying mechanical engineering he progressed to a Commercially endorsed Yachtmaster and spent the summers skippering throughout the Mediterranean. After a year of office life working in the tech sector Jamie chose to swap the desk for the waves and became full time yacht crew. Captaining SY Solitaire a 75ft sloop on charter for season, multiple stints on superyachts and ocean crossings. He has amassed in excess of 15000 miles at sea. He is a keen skier and enjoys anything out on the water or outside.
Captain
Brenden is an engineer, sailor, and climber currently based in Charlotte, NC. He grew up in Connecticut, sailing on Long Island Sound at the Longshore Sailing School during the summers, and has been chartering monohulls and catamarans for about 15 years. Currently working as a structural engineer inspecting bridges and dams across the US, Brenden previously spent 9 years as an engineer in the Middle East and West Africa, and is also a partner of a bar in Brooklyn, NYC. Brenden enjoys the camaraderie and culture sharing that’s often so quickly found in a port, as well as the privacy and natural beauty of a secluded anchorage.
Captain
A native to Maine and unabashed thalassophile, Jon has worked on the water for over 12 years and has sailed over 15,000 miles. On land he has walked the width and breadth of two nations and has lived in cities from New York to Honolulu to Bangkok. While solo journeys have incredible value, for him, it is the communal expeditions in outdoor settings that have defined Jon’s time in the wilderness as they provide the rare combination of camaraderie and growth that only can be known through group adventure. He holds a USCG masters license, and has participated in international competitions on traditional 18th century wooden Bantry Bay Gigs, canoed Alaska's Inside Passage rain forest, and operated a marine research vessel for Cornell University. When not on the move, he enjoys living in small island communities off the New England coast.
Co-Founder, Captain, & Operations
Since a young age, Ross Beane has been relentless about sharing his love of wilderness travel with people wherever he goes. Having worked with programs from Alaska to Maine, he enjoys guiding people of all ages and abilities into beautiful and remote locations to foster technical know-how and an appreciation of the natural world. From having studied outdoor education and wilderness emergency medicine, he brings with him an understanding of risk management that keeps everything safe without compromising fun. On tiny boats, very large ones, and everything in between, Ross has made many safe crossings. He has taught sailing for The Wooden Boat School, New York Harbor Sailing Foundation, and the Manhattan Sailing School before joining Dayyan to help start the Sailing Collective.
Captain
Tyler Sauter is a boatman that would fit in on a ship if you dropped him in the ranks anywhere throughout time. As a boat builder, he worked and taught at the WoodenBoat school where he studied traditional methods of construction and restoration and studied boat building at the Landing School in their Marine Industry program. As a sailor, Tyler taught small boat handling at the WoodenBoat school in Maine and has embarked on many voyages on ships big and small. He currently lives full time on his sailboat in the northeast sailing where work and whim may take him.
How It Works
Select private and double cabins are available for each departure. We sail on 45' - 55' monohulls with catamarans offered during catamaran training courses. Upcoming schedule is listed below, select View Course for detailed information about the course and Book Now to register.
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