CaptainJosh Gillespie US 1978
Dog OnboardFriendly dog Cavapoo 0
Number of Crew: 1Languages:

Crew Profiles:
Josh, after a decade on Wall Street, is a recovering banker but is no stranger to tropical islands. He has been a lifelong professional mariner in one aspect or another. At 17, he joined the US Navy as an electronics technician and served for four years. After college, he spent another 8 years on active duty as a surface warfare officer, taking on a wide variety of roles, from navigator to engineering officer on ships such as a guided missile destroyer, an amphibious ship, and a submarine tender. He also undertook several transoceanic crossings. In his last 10 years with the Navy Reserve, Josh worked for the Navy’s Military Sealift Command and retired in the fall of 2022. He has lived in various places, including across the US, as well as in Italy, Spain, Japan, China, Hong Kong, and Singapore. Sailing has always been an important hobby for him, be it renting sailboats on Naval bases, crewing in local regattas, or entertaining friends with weekend island trips on his previous daysailer in Hong Kong. He's an avid and curious explorer, but meeting new friends, hosting, and entertaining brings him the most joy. He earned a degree in economics and history from Fordham University and a graduate business degree from NYU Stern and the Hong Kong University of Science and Technology. At different times, he has spoken functional or fluent Mandarin, Cantonese, Japanese, and Spanish.

In his free time, he continues his three-decade passion for scuba diving, learns to spearfish, practices yoga, keeps up with the financial press, enjoys snowboarding, and takes cooking classes wherever he can. 


Though at times it seems Captain Josh is actually Pip’s emotional support human, Pip is a reliable and devoted 1st Mate. Friendly to a fault, he loves being around people and loves to photobomb his guests. Non-shedding and hypoallergenic 20 lb Cavapoo, people love him snuggling up them on a couch or hammock.. It’s rare that I’m not napping, but I love chasing squirrels, chasing rabbits, running up and down the beach, and of course, chasing blowing leaves.

Josh Gillespie

Onboard Dog