When Patrick Kenealy wants to take his 36-foot yacht for a spin, he doesn’t need to round up a crew. Instead, as he did one clear Sunday morning in September, he simply pulls away from his slip, cuts the engine, wraps a line around an electric winch, steps on a button, and without leaving the wheel of the boat, hoists the mainsail. Just like that, the Sea Witch catches the wind and begins to cut through the dark blue water of San Francisco Bay.

Kenealy is an energetic 46-year-old, a general partner at venture capital firm IDG Ventures. He grew up sailing along the New England coast with his father and brother, but when he moved to California in 1990, work and family left no time for weekends on the water. Now that his children are 11 and 15, he wants to give them an experience like his own.

Until recently, the dilemma for time-pressed sailors like Kenealy was that boats that were big enough to use for taking family and friends out on for an afternoon were designed for long trips, while those made for daysailing were usually too small—under 25 feet long. But his boat, an M36 built by Morris Yachts in Maine, is large and stable enough that he feels comfortable taking his children out on the occasionally rough and blustery bay. It has room for guests to socialize above deck and open space below for preparing drinks and relaxing. It has the classic lines of a vintage sailing vessel but incorporates the latest technology, making it relatively simple for one person to sail.

Kenealy has been out on the Sea Witch more than 100 times since he bought the yacht nearly two years ago, and he often uses sailing excursions in place of golf outings to size up potential investment prospects. “When you take people out on the boat, you can tell a lot about them—how useful they make themselves, how they act,” he says. “Out here, the quality of your conversation changes.”

Just five years ago, a boat like Kenealy’s would have to have been custom designed, because only cruisers capable of making long trips were built this big. But cruisers typically have little space for socializing, and their large interiors are carved up into sleeping cabins, a galley (kitchen), and storage space. Boatbuilders figured that if you were spending half a million dollars on a boat, you should be able to sail across the ocean on it—even if you never planned to.

But a handful of high-end yacht builders, including the Maine-based Hinckley Co. and Morris Yachts, started paying attention to buyers like Kenealy. They realized that even customers who can afford to drop $400,000 to $1 million on a yacht—and in some cases, especially those customers—don’t have time for long sailing adventures. “Family commitments, second homes, and other activities like golf and skiing are all competing for people’s time today,” says Cuyler Morris, president of Morris Yachts. “In order to keep sailing in people’s quivers, we recognized that we had to make a boat that was easy to sail and a joy to own.”

Ted Fontaine, who made his name creating handcrafted yachts of more than 100 feet in length, was the first to take a stab at this market. Based in Portsmouth, Rhode Island, he heard customers say they wanted a big, attractive boat on which to take their friends out for an afternoon or a quick weekend trip (or, as one of his customers put it, a vessel that “sails eight, drinks six, and sleeps two”).