During the 1998 Orange Bowl in Miami, Richie chartered a 47 foot sailboat on Biscayne Bay and took several of his classmates from the University of Tennessee sailing for the day. Not only was it fun, but he was able to see firsthand how rewarding it was to introduce people to sailing that otherwise wouldn’t have the opportunity. Over the past 25 plus years, Captain Richie has exposed thousands upon thousands of guests to the magic of sailing on a multitude of vessels spanning the entire Gulf of Mexico, Eastern Seaboard, Bahamas, and Caribbean.

Captain Richie Mahoney

Owner & Founder

Captain Richie holds a 1600 / 3000 ton Master’s license from the United States Coast Guard. He began his sailing career at the age of 4 on the mountain lakes of Northeast Tennessee and Southwest Virginia. He has sailed on the collegiate level, done extensive coastal cruising, made ocean passages, and has skippered in several high profile regattas. Professionally, he has captained a wide array of vessels from the offshore oil and gas industry to offshore tug boats to high capacity passenger vessels and everything in between.

Captain Richie has been featured in several magazines such as Southwinds, Canvas Rebel, Voyage Tampa as well as the Sailing Legends podcast.


Captain Michael Martin

Tampa, Florida

Operations Manager

USCG Licensed 50 Ton Master



Captain Glen Sears

Buffalo, New York

USCG Licensed 100 Ton Master