Captain Jay Phillips has worked in just about every aspect of the sailing industry and is truly a humble expert. Jay started his first Charter Boat, the Rendezvous, in Ocean City Maryland when he was 21 years old. For three years Jay entertained thousands of guests on the backwaters and Ocean Front of Ocean City Maryland, Dewey Beach, Rehobeth, and Lewes Delaware.

After the Rendezvous Jay moved to Annapolis and was fortunate enough to learn from several of the best Yacht Racers in the industry. Other than Racing J22's, J24's, Melges, Mumm 30's, International 14's, J105', J120's, Santa Cruz 70's, Frers 65's, J30's.......... Jay ran charter boats for Watermark Cruises, Northeast Wind Yacht Group, JWorld Sailing School, Chesapeake Sailing School, and taught sailing under the auspices of the ASA and US Sailing. He is currently certified to teach over 15 course levels of sailing.

Next was the British Virgin Islands, where Jay started out working with Sunsail, Moorings, BVI Yacht Charters, Horizon Yacht Charters, and others as a sailing instructor and yacht captain. Over a 10 year period Jay delivered more than 30 yachts back and forth from the East Coast to the Caribbean, accumulating over 50,000 offshore miles. Jay finished his career in the BVI as a Sailmaker and loft owner for the industry leader, North Sails.

Currently, Jay is looking for new adventures in Southwest Florida with his new boat, Stargazer, a beautiful classic of the fiberglass era, Pearson 36. You will be hard pressed to find anyone running a charterboat with such an extraordinary breadth of experience in the Sailing Industry.

Jay has held his USCG Masters License since 1990. (click here for Jay's Full Resume)