Wayward Sailor – 40+ Years of Authentic Sailing Adventures

Welcome aboard! With over 40 years of sail-chartering history in the Virgin Islands, Wayward Sailor offers an unforgettable, hands-on experience that captures the true spirit of the sea. This isn’t your typical boat ride—it’s authentic sailing for genuine adventurers.

Whether you’re a seasoned sailor or a curious first-timer, Captain Phil and his crew will take you on a personalized journey filled with island stories, snorkeling stops, and Caribbean breezes. Book your adventure today and experience the magic of St. John from the deck of a classic sailboat.