About Us! - Wayward Sailor
Wayward Sailor by definition:
"In search of one's own destiny"

The Wayward Sailor is in excellent condition and is very safe and comfortable with all the necessary safety equipment and more. Capt. Phil is very safety conscious and has a spotless record in the last 30 plus years of boating experience.


She sails beautifully and provides a leisurely sail or an exciting sailing adventure for the first-time boater or experienced sailor.

The spacious cockpit has lots of room to stretch out and relax. The bow of the sailboat provides romantic "alone" time for viewing the sunset or for a private family adventure.

The sails complement her gleaming white hull with a classic look.

The traditional tanbark sails were carefully designed and made by Capt. Phil's friend, Sailmaker Manfred Diettrich of St. Thomas. At 80 years of age, he is still a skilled craftsman who was apprenticed as a sailmaker at 14 years of age in Germany.


The Wayward Sailor is a classic 30' Islander sloop built in Cosa Mesa, California in 1966 by the Wayfarer Corp.

Since Capt. Phil has owned her for the past 30+ years, he has logged well over a hundred thousand miles under her keel, traveling throughout the Caribbean and the Bahamas.

With beautiful lines and well-appointed details, the Wayward Sailor provides every comfort for your day aboard. She has a full galley, optional shade, a cushioned cockpit and a head (onboard bathroom) and an easy access boarding ladder.

The Wayward Sailor was named after a wonderful book, "The Saga of the Wayward Sailor", by Tristan Jones. Tristan was a great adventurer, author, and sailor, always sailing with his three-legged, one-eyed dog, Nelson, named after Admiral Nelson of the Royal British Navy. His books are still in print.

Travel to/from shore to the vessel is by comfortable, safe dinghy.


Capt. Phil Chalker
PO Box 37
St. John, VI 00831-0037
(340) 473-9705
Email Capt. Phil