There's a First Time For...Sailing Offshore

I took up sailing in my 30s after poking around Maine for some time taking photos. My first sailing experience was aboard a windjammer in Camden, and it was glorious, but it was the photos I’d taken of the small sailboats at anchor nearby that really stuck with me.
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I could not get Nova Scotia out of my head.

I took up sailing in my 30s after poking around Maine for some time taking photos. My first sailing experience was aboard a windjammer in Camden, and it was glorious, but it was the photos I’d taken of the small sailboats at anchor nearby that really stuck with me. Sailing lessons followed, as did the books of Lin and Larry Pardey. Soon my wife and I owned our first boat, an aging flush-decked 20ft double-ender. 

Somewhere around the time we graduated to a 25-footer, I read an article about a race from Portland, Maine, to Yarmouth, Nova Scotia. I wasn’t a racer, but the idea stuck: someday I would sail to Yarmouth. A decade or two went by, and then one day I saw a 60-year-old face in the mirror and told myself,“If you’re going to do this, you’d better get on it.” I called my buddies Jim, Carl and Peter to see if they were interested. They immediately signed on. Now I would really have to do this, but there was just one problem: I had never been offshore. 

Yarmouth is almost exactly 200 miles east of our mooring in Falmouth, Maine. It’s not like sailing to Bermuda, but it’s far enough and cold enough that you could get yourself into real trouble. The crew and I met that winter to bat around ideas. From that point on, the trip was not just a dream, but a plan. It was official. It was on our calendars for July. I figured on a two-night passage.

There was a lot of work to be done and, as these things inevitably go, a fair amount of cash to spend. The various tasks fell into three categories: 1) things the boat needed anyway; 2) equipment specific to this trip; and 3) trip planning.

Loda May, our 1984 Cape Dory 31 twin-headsail sloop, still had her original standing rigging, so I replaced it. The first reef in our mainsail was quite modest and our second reef was not that high, so I added a third one to be on the safe side. In anticipation of gale conditions, I also asked the loft to put a set of reef points in our hanked-on staysail, after which I mounted the necessary blocks and rigged the extra reefing lines.

I replaced the long-dead depth transducer. Since that meant getting inside the steering pedestal to run the new cable, I also lubricated the chain and checked the steering cables and attachment points.

Most of the boat’s fuel lines were outdated, so I installed new ones. I bought a spare electronic fuel pump for the Universal M-25 engine, and packed it along with the necessary hose barbs. A trip to Wal-Mart netted three excellent 5-gallon jerry cans, which I lashed to a length of composite lumber I U-bolted between two stanchions.

The elderly VHF radio needed to be upgraded to a new one with DSC. While I was at it, I dropped fifty bucks more for AIS reception. That meant doing some wiring between the radio and Loda May’s multifunction display, so we could see the ship icons on screen and let the DSC know where the heck we were. We installed an electronic hailer/horn on the mast, and ran wiring to connect it to the radio. Being able to sail or motor in the fog while the radio automatically generated a fog signal was a great improvement and very comforting.

I am not sure I would have bought an EPIRB just for coastal cruising, but for a trip like this one I felt it was necessary. I chose a unit with GPS, swallowed hard at the price, and felt better for it. I had never liked the way the lee cloths in the main cabin were attached, so I removed and reattached them. I bought a good-quality manual bilge pump and stowed it in the cockpit locker as a backup to the two bilge pumps already onboard.


The four of us each threw in a C-note and rented a liferaft for the 10 days we might conceivably need it. The raft was assigned to the cabin sole and was tied to the table leg with a single easily released line. The first aid kit was updated, and I purchased new flares. We all bought personal strobes, and I replaced Loda May’s ad-hoc ditch bag with one that was properly stocked.

Nova Scotia research material began to pile up. An electronic chart for Canada arrived. My buddy Lenny gave me a Canadian courtesy flag, and I researched customs and immigration procedures. I also chatted up some folks who had already sailed the same waters. 

I chose Jim as my second-in-command, based on his sailing experience. Carl volunteered to take on provisioning and maintaining the log book. Peter is a psychiatrist in the real life, so we figured all bases were covered. 

Carl agreed to bring his handheld GPS to back up my handheld unit, which backed up the ship’s plotter. We planned to keep jacklines rigged the entire trip, and all crew would be required to stay clipped on at night. The skipper’s naptime was proclaimed sacrosanct. I created a waypoint at the spot where we’d need to change chart cards. Call me compulsive.

In June, we went for a shakedown sail in snotty weather. We inspected Loda May again from stem to stern. Sometimes I thought, “This is overkill,” until I remembered all that could go wrong if we weren’t adequately prepared. A few times, I wondered if I was really ready for this, until I remembered that in this life, there are no guarantees. So finally, at some point long before we left (maybe, say, eight hours), I declared we were ready.

On a clear, windless July morning, we set out on a heading of 88 degrees true from  Casco Bay’s Halfway Rock. After motoring for four hours, we were gifted with a perfect 10-15 knot breeze out of the south-southwest. Up went all three sails, and then, having eased away from the lobster-trap-strewn Maine coast, we deployed our Sailomat 601 windvane. We staggered our four-hour watches so that two of us were always on, but a body changed every two hours. The wind held steady, porpoises swam alongside, day turned to night, shooting stars crossed the sky, and tall tales were told. The next thing we knew, it was morning and a large courteous container ship was changing course to pass astern of us. We just kept trucking along at 6 knots.

At some point, it dawned on me that at the rate we were going, it would only be a one-night trip. I guess you could say that was my only “disappointment.” Perfect conditions continued, up went the Canadian and quarantine flags, and by 1700 hours on Day 2 we found ourselves safely tied up in Yarmouth Harbor. We had never changed course, never added or subtracted sail area, hardly touched the vane gear, and here we were! Thirty three hours had just sailed by. The dream had been fulfilled. Just like that.

Yarmouth is a funky, friendly town and deserved a longer visit. But my three shipmates had only a week to go cruising, so we spent one night there and sailed for Brier Island around noon the next day. Over the next two nights we enjoyed a brief tour of the Bay of Fundy, complete with breaching whales, fresh crab cakes and massive tidal ranges.

We re-entered the United States at Bar Harbor, Maine, where we tied up on the splendid waterfront, cleared customs and capped off the trip with a festive dinner ashore. I traded out the guys and the liferaft for my newly arrived wife and cat, and began a slow two-week cruise back to Falmouth. 

I’m glad I chased my dream, and encourage you to pursue yours. As you do so, remember that no matter how much you prepare for the worst, there is simply no way to guarantee that things won’t turn out to be absolutely perfect. 

Photos by Dean Abramson

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