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.
Basic Keelboat 101
Coastal Cruising 103
Bareboat Charter 104
Coastal Navigation 105
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.
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.
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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