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5 Ways to Go from Cruising to Adventuring

When I first purchased my 1987 Beneteau First 375, I had visions of mimicking the exploits of Tania Aebi, the Martin family and other daring sailors I admired.
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When I first purchased my 1987 Beneteau First 375, I had visions of mimicking the exploits of Tania Aebi, the Martin family and other daring sailors I admired. Seven years later, I’ve yet to venture more than 20 miles offshore, but have still managed to have more than my share of adventures. Here’s how:

1. Take the train

Instead of keeping your boat in one place and sailing every weekend to the same destinations, leave your boat in a new place each weekend and use the train to get home. My wife, Alina, and I explored the Connecticut coast that way in 2009 and the Long Island coast in 2010. We would slowly sail along the coast on Saturday and Sunday, drop the boat on a mooring, and then take the train back to NYC for work on Monday. On Friday, we’d resume our voyage, returning by train to wherever we had left the boat. It was like having a summer home in a different place each weekend.

2. Sail at night

We eventually reached the end of the railroad line—Greenport, on the eastern end of Long Island—but we had our eyes on Nantucket. Sailing there overnight was both efficient and worth doing for its own sake. By early evening, we saw all of the other boats sail home. After that it was just us and the wind and waves and the sun setting over the water. The darkness heightened what we heard and felt. The sunrise on a becalmed sea was even better.

3. Repair something underway

After many weekends of “train sailing” and a couple of overnight passages, something will undoubtedly break. In adventure tales, sailors often jury-rig ingenious fixes, and you can try the same. Alina once patched a hole in our inflatable at night while sitting in it in the middle of a bay. As part of the process, she deflated both chambers so the air pressure would not push the glue out. Not only did she save the dinghy, we also learned it won’t sink when deflated.

4. Rely on the kindness of strangers

If you’ve completed steps one through three, you’ve mastered radical self-reliance—you can go anywhere you want, day or night, and you don’t need anyone’s help to do it. Next, try the opposite. You’ll find that when you do unusual things, strangers are more likely to help. For example, from the train station, walk down a suburban road with a watermelon in one hand and an extra sail in the other, and someone will inevitably offer you a ride to the marina.

5. Sail to a different cruising ground

Once we explored just about every port on Long Island Sound, it was time to go somewhere new. The Chesapeake was an obvious choice, both because it’s a good place to sail and because we have family in the area. Our favorite part of the Chesapeake is the northern part—Bohemia River, Sassafras River and Still Pond—where you can swim in fresh water, and the temperature is already in the upper 70s by late May. Best of all, we got to use all of the skills we acquired closer to home. 

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