Vineyard Haven is one of the great anchorages for wooden boats in the United States. The magazine asked Matthew Stackpole, executive director of the Martha’s Vineyard Historical Society, to identify and describe his six favorite boats in Vineyard Haven harbor.

"I was pleased, humbled, and terrified by the request,” writes Stackpole, who was raised in Nantucket and Mystic, Connecticut, and served as first mate on the topsail schooner Shenandoah – one of the vessels he names 
here – from 1967 through 1970. “First, it would have been easier to select thirty boats, and second, I feared being killed by the owners of the vessels 
not listed. What follows is unabashedly subjective and unscientific, but I have tried to select a variety of vessels that demonstrates the scope and diversity of the harbor. Think of 
what follows, then, as an appetizer that I hope will inspire the reader to take a look and enjoy the amazing 
array of craft that makes this harbor so interesting.”

Stackpole, by the way, didn’t include the twenty-foot 1925 Herreshoff Fish-class sloop he owns with his wife Martha.

Banzai

Built in 1905, one of a fleet of eighteen ordered by the New York Yacht Club, this New York 30 represents the beauty and amazing sailing qualities that came from the mind and yard of Nathanael G. Herreshoff of Bristol, Rhode Island – one of our country’s greatest boat designers. Splendidly restored over four years by Carlos D’Antonio of West Tisbury, who has owned her since 1988, Banzai displays all the best attributes of simplicity and 
elegance in a Herreshoff design. Banzai is amazingly fast and maneuverable; she can tack (that is to say, turn through the wind) in her own length. One of the great joys of owning her must be seeing the looks on the faces of those sailing much more modern “racing” vessels as Banzai cruises past them – at 100 
years of age.

Shenandoah

Lying dramatically at her mooring at the head of Vineyard Haven harbor for the past forty-one years, Shenandoah 
has become a symbol of the Vineyard 
for people coming and going. With her raked masts and square yards, she has great character, and many times I’ve heard children say, “Look, there’s a 
pirate ship!” It was she who first brought me to the Vineyard in 1966, and I had 
the great experience of sailing her in the coastal-cruising trade for five summers. One hundred and eight feet long on deck, she has no engine, relying on her 7,000 square feet of sail. It is hard to 
describe the thrill of Shenandoah beat-ing to windward up Vineyard Sound at twelve knots with all sails set. The passion of Robert S. Douglas for traditional 
sailing ships got her designed and built 
in 1964; Shenandoah herself attracted the men and women who keep alive and vital the traditions of wooden-boat design and construction on Martha’s Vineyard – most notably at the Gannon and 
Benjamin Marine Railway, but also in barns, sheds, and schools all over the 
Island. Any harbor would be improved 
by Shenandoah’s presence; how different Vineyard Haven would be without her.

Malabar II

Jim Lobdell and his wife Ginny of 
Tisbury have owned several interesting vessels, and I think Malabar II is most fortunate to be the one they settled on. Jim has extensively rebuilt her; this John Alden design is one of the queens of 
the American Schooner Association, 
participating in regattas up and down 
the East Coast. Equally at home on Vineyard Sound or a trip to Maine or 
the Chesapeake, Malabar demonstrates how efficient and handy her gaff schooner rig is. The Lobdells can sail 
her by themselves, or bring along a large crowd of friends. Another example 
of this design – Jeff Robinson’s Phar 
Luong, which Jeff built in southeast Asia – is moored nearby. Warner Bros. so admired the Malabar II designs that it hired both vessels to star in the Kevin Costner movie Message in a Bottle in 1999. In addition to the fame, they 
both returned with new suits of sails!

Juno

Launched two years ago, Juno is the largest sailing vessel to be built on the 
Island since the 279-ton brig Island Queen was launched from what is now Martha’s Vineyard Shipyard in 1860. 
Designed by Nat Benjamin and built by Gannon and Benjamin, she comes from the same ethos of yacht design that 
produced the first Gannon and Benjamin boat in 1980 – the Canvasback called Sally May – and the Bella class nestled just north of the Steamship Authority wharf in Vineyard Haven. Juno reminds me of the beautiful schooner Brilliant at Mystic Seaport Museum, and the sixty-three-foot Alden schooner When and 
If in Vineyard Haven – but Juno has her own wonderful strengths and characteristics. She is equally at home on Vineyard Sound or making an ocean passage. 
Her lines are exquisite, her construction strong and elegant. Below decks, the joinery is worthy of the finest wooden furniture. Nat’s designs build on the designs of those who went before him, informed by his own experiences on the water. The combination results in beautiful vessels that sail well in any sea.

Kanga

Erford Burt of Vineyard Haven, who died in 1993, was a versatile boat designer and builder. He began his career in 1927, working for Manuel Swartz Roberts at what is now the Old Sculpin Gallery in Edgartown. Before starting Burt’s Boatyard (now Maciel Marine) on the Lagoon in Vineyard Haven, Erford worked for Martha’s Vineyard Shipyard, and there, in the mid-1930s, designed the Vineyard Haven 15. More than forty were built, some in fiberglass. Fast, handsome, and able, the 15 – a reference to waterline length in feet – trained several 
generations of Vineyard sailors. Kanga, pictured here, was the eighth hull in the class, built in 1938. Owned by Denys Wortman of Vineyard Haven and 
restored for him by the Gannon and Benjamin Marine Railway in 2000, Kanga embraces the tradition of Vineyard boat design, construction, and repair 
carried on by Philip Hale at the shipyard and Ross Gannon and Nat Benjamin 
at the railway. As Hale says of the 15: “They take you for a great sail and they get you back.”

Violet

Beautifully restored by Gary Maynard in the cement building at Five Corners in Vineyard Haven – and sailed halfway around the world by Gary, his wife Kristy, and their two children – Violet’s admirable shape and rig is noticeably different from most of the other vessels in the harbor. Designed as a fishing vessel in Scotland, she demonstrates that function, seaworthiness, strength, and beauty can all go easily into one design. Gary’s ability as a shipwright is well known, and I admire not only how strongly built (and rebuilt) Violet is, but also Gary and Kristy’s attention to detail and the meticulous way in which she is maintained. The effort and the results, however, do put a lot of pressure on the rest of us mere mortals.