After graduating from college in 1985, Gary Maynard established G. S. Maynard & Co, Inc., also known as Five Corners Shipyard, in Vineyard Haven, Massachusetts. Over the next twelve years, he and his crew restored historic wooden vessels, ranging from an eight-foot Bahama dinghy up to the ninety-foot pilot schooner Alabama, now sailing out of Vineyard Haven Harbor. Their restorations have been widely recognized by such institutions as Mystic Seaport Museum, have been featured numerous times in Wooden Boat Magazine and have won multiple awards at prestigious classic boat shows around the world.

In 1998, Gary closed down the Shipyard, sold the boatbuilding machinery and he and his wife and business partner Kristina took their growing family on an ocean voyage aboard their own classic boat Violet. They and their two small children sailed their 100-year-old boat through the Caribbean, the Panama Canal and on to the South Pacific, Hawaii and even as far north as Glacier Bay, Alaska.

On their return from their adventure, Gary and Kristina established Holmes Hole Builders, this time focusing on the construction of high-end architectural residences on Martha’s Vineyard. Under Gary and Kristina’s direction since 2001, Holmes Hole Builders has built over $200,000,000 worth of the finest homes on the island, as well as several notable commercial properties. Their projects have been widely published, in periodicals such as Architectural Digest, Dwell, Fine Homebuilding, Boston Home, House Beautiful, The Wall Street Journal, Vineyard Style and Martha’s Vineyard Magazine.

Gary is an expert traditional boat sailor, an avid cyclist and a published novelist. He holds a Bachelor of Arts in Linguistics, Phi Beta Kappa, from Brown University. He resides in West Tisbury, enjoying an “empty nest” with Kristina, now that their two children are successfully launched.

Kristina serves as Gary’s most trusted advisor, particularly when it comes to people-related issues, from employee relations to contract negotiations. She works in the office as our marketing director, but more importantly behind the scenes at HHB, creating and nurturing our “family” culture, including sailing aboard Alabama, organizing our unique company Triathlon Team, and managing the many unusual company benefits that help our people feel appreciated, respected and passionate about their jobs.

Although she grew up in Canada, Kristina has lived on the island since she was fourteen and attended the Martha’s Vineyard Regional High School. She seems to know and be known by everybody who lives here. Kristina spent summers racing at the Vineyard Haven Yacht Club before falling in love with sailing bigger boats. Kristina helped to restore and maintain the Maynards’ lovely 1911 sailboat Violet, and served as her Mate for many years, cruising New England, chartering out of Vineyard Haven, and voyaging to the South Seas and Alaska. She has also worked as a sea cook aboard the schooners When and If and the Sylvina W. Beal and as a housepainter, a sailmaker, a gymnastics teacher and as marketing director for the Vineyard Playhouse. Somehow she managed to be a full-time Mom as well.

These days, Kristina is an active dressage rider, competing on her Oldenburg mare Dia all over New England. Kristina loves to travel and enjoys hiking adventures with Gary, but is also happy gardening at the couple’s new home in West Tisbury. Kristina is an active ally for indigenous and LGBTQ communities, as well as an advocate for affordable housing on Martha’s Vineyard.