Browse our upcoming sailing expeditions below.
ARC Rally Atlantic Crossing | Gran Canaria – Saint Lucia
November 18 - December 18 2025 | $9995 Sold Out ...
Trade Winds and Turquoise Dreams | BVI – Dominican Republic
13 March - 23 March 2026 | $4990 Sailing from ...
Crossing Hemingway’s Path | Dominican Republic – Key West
27 March - 10 April 2026 | $5990 Sailing from Dominican ...
How to Sign Up:
First, pick an upcoming trip that interests you and place a deposit. We’ll send you all the details ahead of your journey, with what to pack, a tentative itinerary, and what to expect. You’ll meet us at the dock and be introduced to the captain and the rest of the crew. We’ll have all the necessary provisions to welcome you aboard, including comfortable sleeping berths and delicious meals. The first day or two are spent getting to know the vessel and preparing to sail safely. You’ll help us work and sail Sea Dragon, building sailing skills, while having a life-changing adventure.
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