The Master's Pocket Cruiser

1983 Custom Thomas Gillmer Trawler — $33,000

You wake up to the sound of water lapping against the hull in a quiet, fog-draped New England cove. You step up into the enclosed pilothouse, make a cup of coffee, and fire up the 58-horsepower diesel engine beneath the floorboards. As you pull the anchor, you raise the small steadying sail, kill the engine noise, and quietly glide out of the harbor at 6 knots. You aren’t in a rush to get anywhere, and your boat burns less than a gallon of fuel an hour.

Currently located in Maine, this 30-foot pocket trawler is a maritime unicorn. It was designed by Thomas Gillmer, the renowned naval architect and former chairman of the US Naval Academy’s Marine Engineering department. He designed it specifically for his own retirement cruising. Built at the prestigious Martha’s Vineyard Boatyard, it is a brilliant hybrid: a highly efficient diesel trawler built on a sailboat hull, complete with a small mainsail and jib for wind assistance and stabilization.

For Boat 2 of our “Custom” week, we are looking at the ultimate subcategory of bespoke boats: The Designer’s Own Vessel. When a legendary naval architect spends his entire career designing famous boats for other people, what does he build for himself when he retires?

You get a boat where every single line, system, and weight-distribution metric was obsessed over by an expert. Normally, buying a master architect’s personal boat costs a fortune. But because this 30-foot pocket trawler is 40 years old and doesn’t belong to a recognizable mass-production brand, the market has completely overlooked it. The “Smart Money” buyer recognizes the pedigree, the incredibly rare Martha’s Vineyard Boatyard construction, and the absolute steal of a $33,000 asking price.