Captain Dean has over 15 years experience sailing Cayman waters and is the owner of Point Blue Sailing along with his wife, Karen. Having spent a lifetime in sports and recreation with a degree in leisure management, Captain Dean is a retired professional squash player who moved to Cayman in 2003 and spent nine years coaching squash and developing junior squash programmes in Cayman. Sailing quickly became a passion for Dean after buying a 30-foot cruiser for family sailing in the early 2000s.

While spending several years as a stay at home dad to three kids, Dean studied for the Yacht Master examinations through the Royal Yachting Association and has spent many days on Cayman waters, as well as blue water sailing voyages across the Caribbean and Gulf of Mexico as crew and as captain. Captain Dean has also participated in the Clipper Around the World Ocean Race in 2022 and again for Leg 6 of the 2023 / 24 edition of the race where he crossed the North Pacific from China to the USA in March / April of 2024.  The crossing took 28 days non-stop from Qingdao, China to Seattle, USA finishing in 2nd place.