Western Long Island Sound offers a wide variety of sailing conditions, anchorages, and activities. The St. Barts Sailing kept Bright Star, a 1980 Sabre 34, at Glen Island Yacht Club in New Rochelle for close to twenty years.
The sailing season included many days and evenings on the Sound, including Thursday evening racing, plus a few overnight trips to further destinations.
Trips to New York Harbor were always popular as well as challenging. The passage through Hell Gate, where the East River and Harlem River meet, can only be made at certain stages of the tide. At other times the tidal flow is so strong Bright Star under full power was pushed backward by it. We learned this the hard way by mistiming a northward journey once.
Once in the harbor the sailors faced constant shipping traffic, with everything from the Staten Island Ferry to replica tall ships plying their trades across these waters. A favorite refuge for an overnight stay was the shallows between the Statue of Liberty and Ellis Island. There are few places in the world where a sailboat can rest in such close proximity to sites of such historical and national significance.
When we chose to head east, Port Jefferson on the north shore of Long Island was a natural destination. Getting there took a full day of sailing, which could be rewarded with a good seafood dinner. With a completely protected harbor and quaint fishing village feel, Port Jeff’s only drawback was the frequency of the ferry that goes between it and Bridgeport, Connecticut.
Port Jefferson was also a convenient stop on the way to Block Island. Block lies at the eastern end of Long Island Sound, a couple days sailing from New Rochelle. We made the trip with Bright Star a few times, and on other occasions we chartered boats in eastern Connecticut to sail over.
There are pros and cons to both approaches: Sailing Bright Star took several more days and more organization; chartering a boat is expensive and you’re never quite sure of the quality of the vessel until you see it. Such was the case on our last charter: the big old Morgan we’d arranged for was a floating bathtub with a park bench mounted on the stern. Midway to the island, in very light wind, the engine died. Fortunately, it worked again early the next morning when the wind had kicked up and our anchor dragged in the crowded Salt Pond.