Everything he can do in a bigger boat and more

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Bill Dobson has gotten around on sailboats ... but the 25-foot sailboat he bought used two seasons ago has made him a pocket cruiser convert.

Bill Dobson has gotten around on sailboats. Growing up in the Midwest, he’s raced all kinds of performance boats, from Ynglings to E-scows, and covered the Great Lakes on big-boat classics, including a Pearson 35 and a 75-foot Alden ketch. But the 25-foot sailboat he bought used two seasons ago has made him a pocket cruiser convert.

Read the other stories in this package: Pocket Change   Trailerable Cruiser Specifications

The Offshore 25 from Eastsail Yachts of Bow, N.H., was designed by Eliot Spalding in the early 1980s as a “rugged, trailerable pocket cruiser … for the long voyage.” With its full keel and transom-hung rudder, choice of sloop or cutter rig, and complete accommodations, including an enclosed head, it fits the bill. Yet the 8-foot, 6-inch beam makes it legal to trailer without permits, and auxiliary power is a 20-hp diesel.

Small, seaworthy, easy to handle and with a simple but complete layout, the Offshore 25 was just what Dobson had been looking for. “It was right up my alley,” he says. “It had classic lines, and I liked the cutter rig. That divides up the sails; they’re smaller and easier to deal with by yourself. The accommodations were small, but they work for two people. And there was enough headroom for me.”

After a 30-year hiatus from boating — “raising a family, mortgages” — Dobson’s enjoying every minute back on the water. Each year, he’s extending his cruising grounds. “The first year, I did a lot of coastal cruising in Casco Bay, anchoring every night,” says the 54-year-old consulting engineer from Spencer, Mass. “It is also great for gunkholing. I can go into those nice, small coves that are out of bounds for bigger boats.”

This past year, Dobson started doing what he calls “sails to nowhere.” He drops the dock lines at his GreatIsland marina, points the pocket cruiser in the general direction of the Gulf of Maine, and “sets out into the ocean,” as he puts it. “I’d just sail for 24 or 48 hours, turn around and come back. It’s a different kind of sailing. You don’t have to be navigating all the time; you just relax and enjoy it — tend the sails, read a little bit, sleep, eat a little bit.

“The best thing is how easy it is to go sailing,” he continues. “I don’t have to dig up a crew, and everything on board can be handled by one person or two.”

The boat is relatively small, and Dobson has kept the mechanical and electronic devices to a minimum. “My nav station’s a chart kit on my lap,” he says. That makes the 25-footer easy and inexpensive to maintain. The “to-do” list includes a bottom job, topside paint and refinishing the woodwork, all easily budgeted over time.

“I’d rather have a small boat that can be well-maintained than a bigger one that I can’t afford to keep up as it should be,” Dobson says. “And if the cost is less, I can afford to do more. That’s an important part of it. And that includes things like storage, hauling and overnight slips.”

There’s no sacrificing seaworthiness for size, either. On the Gulf of Maine, 6- or 7-foot waves and 25-knot winds are nothing unusual, and the boat’s not only proved itself a good performer when reefed down, it’s surprisingly dry, too. “I think it’s that clipper bow,” says Dobson.

The pocket cruiser’s stiffest test to date? An offshore summer thunderstorm with torrential rains and 60-mph winds. “It was really no big deal,” he says. “The tiller was lashed down; the sails were all tied up. I went below and rode it out.”

Calmer waters beckon this season. Dobson and the dark green boat with the distinctive tanbark sails will lead the annual cruise of the Bluewater Sailing Club in Maine. “I’ve got the smallest boat in the fleet,” says Dobson. “I’m calling it, ‘Leading from behind.’ ”

And there’s more to come, as distant horizons beckon the little boat. Next year — or maybe the year after — Dobson would like to take the Offshore 25 to the tropics. “It would be a great boat in the Bahamas,” he says. “We’ll see. I feel like there’s really nothing I can’t do in this boat that I could do in a bigger boat.”