Frequent readers may recall that my 1966 Pearson Commander, Good Buddy, was a bargain bin craigslist find; that I dragged her 60 miles to my home in Connecticut from Long Island. Because of the considerable distance between me and the boat (nearly 2 ½ hours by car), and her low-lowRead More

Several years ago I stumbled across the flyer for an intriguing small-boat race, and the kicker was that it was practically in my own back yard. Called the Connecticut River Dinghy Distance Race, the event, which always took place in early May, was sort of a Gumball Rally for localRead More

It’s always neat when what you assume about a given situation is wrong, but in a way that leaves you hopeful about the current state of things. Take last fall, for example, when I checked in on the progress being made on the Mayflower II, a reproduction of the famousRead More

Without a doubt, there are many distractions to help bridge the gap between boating seasons these days, a lot of them thanks to technology. I’m thinking specifically of online classifieds (a personal favorite; see the trouble it got me into), YouTube and Vimeo, sailing vlogs, and streamable documentaries – allRead More

I hate to admit this, especially since my wife has been saying it for years, but I think I’ve got a problem. The problem is that I have too many boats. While this may be true, I take comfort in knowing I’m not alone. Many of us suffer from thisRead More

For the last three summers, since buying my latest “big” boat, I’ve had the same three goals: 1) Hunt down Points East columnist David Buckman while he’s cruising in Maine. Me aboard my Good Buddy and David aboard his Leight, we’d go find a few of those eel ruts he’sRead More

If you’re a sailor, chances are you’ve thought about what it would be like to circumnavigate. The idea of a continuous voyage that lasts years, and involves exotic destinations – it’s heady stuff for the coaster, and there’s no shortage of literature on the topic, which makes for especially greatRead More

In the early 2000s I was lucky enough to race to Bermuda not once, but twice, with Jim Mertz, the “Iron Man of the Onion Patch,” who participated in 30 Newport Bermuda Races between 1936 and 2004 – a record that probably won’t be topped anytime soon. Jim is goneRead More

The first personal account of a trip on the Maine Island Trail I ever read was Steve Callahan’s 2002 article “Reflections at the Water’s Edge,” which documented a trip he and his wife Kathy did on a section of the trail in the pages of “Cruising World” magazine. Callahan andRead More

For cadets between their second and third years at the U.S. Coast Guard Academy in New London, Connecticut, June is a special month. Classes are over, the grass on their hillside campus overlooking the Thames River is green again, and afternoon southwesterlies – warm, and full of promise – haveRead More