Gary grew up sailing around the world on a wooden yawl, worked as a merchant sailor aboard traditional windjammers, tugboats and a drilling rig tender before starting his first company as a shipwright and wooden boatbuilder in Vineyard Haven. He and Kristina re-built their own historic boat and raised their two children aboard, ocean cruising as far as the Caribbean, South Pacific and Alaska. They pivoted to custom homebuilding in 2001 and have now built over $200,000,000 of the finest architectural residences on Martha’s Vineyard. Gary is an adventurer, an avid cyclist and a published novelist. He holds a BA in Linguistics, Phi Beta Kappa, from Brown University.

Kristina brings her charming enthusiasm and love of people to her role as Manager of Marketing and HR. She has carefully built the cooperative, supportive and respectful culture at Holmes Hole Builders, creating a treasured and sought after place to work where the team is allowed to reach their full potential over many years of employment. Having lived on the island since she was a freshman at the high school, Kristina knows simply everyone on the Vineyard. She has worked as a sea cook, a baker, a sailmaker and Director of Marketing for the Vineyard Playhouse, all while raising two children who have now flown the coop. She is an intrepid traveler, an expert sailor and a craftsman in her own right.

For nearly twenty years at HHB, Aaron has managed complex and challenging projects across a wide variety of architectural styles with a cool hand, a discerning eye and exacting expectations. Aaron’s primary role as Project Manager puts him at the crucial interface between owner, architect and our site supervisor, where he is an indispensable voice of reason and experience. He is a lifelong islander and he and his wife are now enjoying empty-nesting, traveling, cycling, hiking and, best of all, doting on their new granddaughter.

Paul worked with Gary and Kristi almost forty years ago as a shipwright on several well-regarded historic vessel restorations and has honed his skills as a fine woodworker ever since. Paul divides his time between running our extraordinary cabinetry shop and providing high-level management for our major restoration work as a Project Manager. Paul is a valued, considerate and philosophical voice at HHB. He can be seen wing-sailing or surfing year-round even on the coldest days. Paul and his wife are also treasuring their time with their baby grandson. Paul has a BA in Philosophy/Psychology from Colgate University.

Mitch has had a steady hand on the helm of our front office for almost two decades. He brings calm, unruffled expertise in construction management as well as considerable small business experience to the table. He can be relied on to track every penny of our clients’ accounts as well as guide operations with a minimum of fuss. Mitch and his wife have successfully launched two children and are holding their own with two more teenagers at home. He still gets out on his bike as often as he can. Mitch has a BA in Health Services Administration from Bucknell University.