
Dick Stuart
Captain Dick Stuart
Captain Dick, a mechanical engineer by training, enjoyed a successful career in construction sales management before turning his lifelong love of sailing into a full-time adventure. He began sailing at the age of 10 in an El Toro on Lafayette Reservoir in Northern California. Growing up, much of his time was spent sailing on San Francisco Bay and bareboat chartering extensively throughout the Caribbean.
In preparation for what he once thought would be a retirement dream plan, Dick continued to hone his sailing skills over the years. He holds a 100 Ton Master’s License with Sailing Endorsement, an FCC Marine Radio Operator Certification, and a Dive Instructor Certification. Known for his excellent reputation as “the troubleshooting ninja,” he uses his knowledge of mechanical systems to anticipate the “what ifs” and keep the experience running smoothly.
Safety is Captain Dick’s top priority for his guests, but fun is a close second. An adventure seeker and water lover, he moved to the beautiful island of Puerto Rico in 2017 and loves sailing the aquamarine waters and island-hopping throughout the Caribbean.
Captain Dick welcomes all guests with his famous captain’s cocktails nightly. He is also an avid cribbage player and is always ready to challenge the best.









































































