Sailing From Annapolis To New York City

Pilgrim at anchor in Spa Creek, Annapolis, during one of the shakedown cruises before leaving for New York City.   Liberty Landing Marina in Jersey City, New Jersey, with the skyline of New York City in the background. (Pilgrim is not in this picture.)


In the early summer of 2007, I sailed as crew aboard the sailing vessel Pilgrim on a voyage from Annapolis, Maryland to New York City. Prior to the New York City trip, I also crewed aboard Pilgrim for two shakedown cruises on Chesapeake Bay.

Pilgrim is a Tayana 42 sailboat recently purchased by Jerome Zukosky, a longtime cruiser and liveaboard. Years ago, Jerome spent a busy career as a reporter, writer, editor, and manager. After he retired in 1991, Jerome bought a Hans Christian 38T which he named Herman Melville; he and Herman wound up spending years cruising the Caribbean. Unfortunately, the boat was destroyed by Hurricane Ivan in Grenada in September, 2004, while Jerome was stateside visiting.

After this disaster, it took Jerome some time to decide what to do. Herman had been insured, so should he take the money and run, or should he buy another boat and resume cruising? Let me add another pertinent fact to the decision-making: Jerome is now 76 years old. Many men his age are tottering around in retirement homes. The fit and able ones are usually consumed by time-filling but non-demanding hobbies. Very few men his age would decide to purchase a 42-foot sailboat, spend a year (and many thousands of dollars) refitting the boat, then take off cruising for points near and far.

But that's exactly what Jerome did.

Jerome Zukosky aboard his boat Pilgrim, in Annapolis Harbor. Click on the right-hand picture to see a bigger version; use your browser's "back" command to return here.

Crewing For Jerome

I met Jerome in the spring of 2007, once Pilgrim had been launched after winter lay-up. His boat wound up next to my boat at Bert Jabin's Yacht Yard in Annapolis. By that time, most of the refitting had been completed and Pilgrim was ready for cruising adventures. Being a conservative sailor, though, Jerome wasn't about to hop aboard and sail away on a long trip. First things first: Make a few shakedown cruises in the local area to test all the gear, work out procedures, and gain confidence in the boat.

In talking with Jerome, I learned that he was seeking crew for the shakedown cruises and a later trip to New York City, where he planned to spend the summer. I think that crewing on someone else's boat is a great way to gain sailing experience, plus it's a heck of a lot cheaper when someone else is paying the bills. I eagerly volunteered, and Jerome scheduled a couple of shakedown cruises on Chesapeake Bay. If everything worked out (with boat and crew), we could then sail up to New York City, which would be Pilgrim's first taste of the ocean and would mark Jerome's return to the liveaboard cruising lifestyle.

In the following sections, I'll tell you about my crewing experiences aboard Pilgrim, plus I'll show you lots of pictures. Although I have divided the story into sections, you can read it sequentially by clicking the "Next Page" button at the bottom of each page.

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