Christopher Lentell Dowley died on Sunday May 26 at his home in Marblehead of complications from a bone marrow transplant for leukemia undergone 10 years ago. He was 66.

Chris was born on March 8, 1958 to Elizabeth and Robert Dowley in Troy, N.Y. He is the grandson of Marion and Leroy Dowley and the great-grandson of Augusta Lentell and George B. Dowley— all of whom were lifelong homeowners on East Chop, beginning in 1902. He spent every summer there well into his 20s until he found the spot where he settled for good — Marblehead, close to the sea.

Chris graduated from the School of Natural Resources at the University of Michigan, Ann Arbor in 1980. His professional life began shortly thereafter when he joined the family business: Wells & Coverly, a men’s clothing store in Troy and Syracuse, N.Y. — the start of his signature bowties and pocket squares.

He later transitioned into a successful 35-year career in financial planning, first with American Express Financial Advisors and then, inspired by his entrepreneurial and adventurous spirit, his own firm, Dowley & Company. He was a leader in the field, constantly studying ways of advancing his knowledge and skills to help his clients. His many clients in the Marblehead and Albany, N.Y. area and beyond greatly benefited from his financial advice as well as his life coaching.

He sold his business a few years ago but within a short period of time decided to get back out into the work world. His love of cycling led him to a job at Marblehead Cycle. He achieved hero status there in a very short time with his organizational skills and, as one co-worker wrote, his insistence on both “vision and focus.”

Like so many seasonal Vineyarders, sailing became one of his lifelong passions. His father taught him to sail in a dinghy on Crystal Lake. Outgrowing the small boat and the pond, he transitioned to East Chop Yacht Club and then on to the Vineyard Haven Yacht Club. He was a keen strategist with an adventurous spirit in all things. That combined with a competitive streak made him a much sought after crew by fellow sailors.

He graduated from Tabor Academy where he raced 420’s and won the nationals in 1976. He had the memorable experience of crewing for Capt. Bob Douglas on the Shenandoah for several summers and then in adulthood back on the Shenandoah with his son. He and his family often chartered a Hinckley Pilot named Sally and sailed for weeks through Vineyard waters, to Block Island, Newport or Shelter Island and explored much of coastal Maine.

He met the love of his life, Laura Freysinger in 1993. They became partners in great adventures including heli-skiing in British Columbia, biking the Boston-to-New York AIDS rides in the ‘90s and, more recently, hiking in New Zealand.

Whenever they were on the Vineyard, if he wasn’t reading on the terrace, no day went by without a sail, a swim, a bike ride or a walk on one of its many trails. Their adored son Gavin, born in 2001, expanded the couple’s lives and became part of the adventurous duo joining them in sailing, skiing and hiking. Gavin also came to be an avid hockey player and fan like his Dad, honing his skating skills beside their home on Redds Pond.

Gavin attended the Waldorf School at Moraine Farm where Chris acted as treasurer for the board over many years, bringing his financial expertise to an organization he loved.

True to his spirit, Chris (and Laura) opened their hearts, home and adventures to two beautiful sisters when they needed it. Laetitia and Raissa joined the family and enriched their lives in countless ways. He was the happiest and proudest Grandpa Chris to Laetitia and Lolo’s daughters, Joanna and Julia.

Chris requested his ashes be scattered in Vineyard Sound and a marker placed in the Oak Grove Cemetery in Tisbury near his grandparents, parents and older brother, Brian.

He is survived by his wife Laura Freysinger, son Gavin Dowley, their daughters Raissa Mulombe (Boston) and Laetitia Mvuezolo, her husband Lolo Bokanga, and two grandchildren Joanna and Julia (Atlanta, Ga. as well as his sisters: Jennifer Dowley (Millerton, N.Y.) and Gillian Dowley McNamee (Chicago, Ill.); and his brother Craig (Mary) Dowley (Ireland and East Chop). His nieces and nephews will greatly miss him: Addison and Marion (Millerton, N.Y.), Malcolm (Boston), Luke (Santa Monica, Calif.), Nico and James (Chicago, Ill.), and Turlough (Castlebellingham, Ireland).

In lieu of flowers, contributions in his name may be made to Waldorf School at Moraine Farm, Beverly MA, Peon Yacht Club or Marblehead Youth Hockey PO Box 1426 Marblehead, MA 01945

A celebration of life will be held in the late summer.