As brisk nights of fall have us closing windows and digging out sweaters, sailors begin thinking about hauling and storing the boat for the winter.

There are two major issues a sailor deals with before the exercise is set into motion. The first is when and the second is where. To some extent, both are related. Fall cruising weather in New England is so spectacular that one never knows when to haul the boat. A weekend or a couple of days appear without a cloud in the sky, some fresh northerly air and the waters simply sparkle. Standing out from the Vineyard, there are few sails in sight, no motorboats (except for those engaged in the fishing frenzy of the derby) and the occasional commercial fisherman. It’s hard to put your boat away knowing that you could miss such sailing.

The ability to make the most of those days on the water and the cozy nights on a quiet anchor in an empty harbor keeps boats on moorings or in slips a little longer. A bright day with a pleasant breeze sets thoughts toward weekend sails, not a delivery run to the boat yard.

I used to work out of an office at the southern tip of Manhattan. From my desk, I looked down at New York Harbor and across to my boat slip in Liberty Landing, N.J. Watching the sailboats from New England heading down the East River, past the Statue of Liberty and south to winter destinations in the Bahamas or the Caribbean, it was all I could do to concentrate on business and not speculate on the next weekend’s cruise.

That speculation and the anticipation of a glorious weekend sail kept me putting off the plans for when to haul the boat. Then Thanksgiving would roll around and I’d need to get serious and let the boatyard know I was coming. Of course, the reality of New England weather in late November meant that I was facing lousy odds and the trip to the boatyard was going to be a cold and miserable experience.

That’s why the when of hauling is related to the where. You can’t be too far away from your yard if you’re heading to the barn in December. Obviously you need a yard with trusted and experienced staff, with secure facilities and with knowledgeable owners. But you also need one you can reach in a hurry.

Since my “when” tied to my procrastination and desire for just one more sailing weekend, I had to scramble for crew to take December trips from Jersey City to New Haven (Branford) Conn. My wife flatly refused the opportunity to motor into the inevitable easterly head wind, to brave frozen spray and shiver in the cabin.

The joy of a night tied up in Stratford, Conn., with a frozen heating system (reverse cycle air conditioner/heaters don’t work when ice builds up at the intake fitting) escaped her notice. The deck ballet on balls of icy hail failed to interest her. The dexterity of working with frozen lines lacked excitement.

In fairness, she did have some sound reasons to avoid these trips. Even wearing modern cold weather gear, with all the polartech and wicking materials and space age insulation, standing in a cockpit, stamping feet and staring into a bitter headwind is something less than thrilling. It’s just bloody cold, nautical mile after nautical mile. The hot cup of coffee, the hot mug of soup, the tot of grog are all fine, but none get to your extremities. Fingers and toes just stay cold, numb and unhappy.

That’s why the 70 or so nautical miles from Jersey City to Branford, Conn., was the limit for our trips to winter storage. Branford happens to be sort of mid-way between Jersey City and Vineyard Haven, which made for convenience. Branford also happens to be the location of a small family-owned boatyard with years of sailboat experience and careful craftsmen. I believe strongly that you should chose a yard like you’d chose a bank or a law firm, not for the letterhead but for the quality of the people who work there. National or regional chains now own many yards, Private equity firms own others; in short, some yards are good, some not. It’s the ability and experience of the people that make all the difference.

My last trip to storage with a 50-foot cutter was an example of when and where conspiring against me. This trip was to take the boat to the broker who would sell her, not to a yard of my choice. My son and I left Vineyard Haven for Annapolis, Md. And yes, I put off leaving until late October. A cold southwest storm system stalled off the coast. Instead of the expected run to Delaware Bay with an easterly off the quarter, we sheltered in the lee of Long Island and beat our way to Jersey City (yet again.) We waited five days for the weather to settle a bit. The next weekend had us beating down the Jersey Shore, slamming into head seas, shredding the jib, motoring through the Chesapeake and Delaware Canal and then to Annapolis. My son and I were safe on the boat, but the when of trip and the where of the yard made our final voyage not a happy romp at sea, but a grinding slog. A grinding, shivering slog.

On the train from Annapolis, instead of the healthy tans of summer, we wore salt-crusted growth of beard stubble and greasy, matted hair. None of the Amtrak passengers wanted to sit near us or hear our sea stories. So much for the romance of the sailor home from the sea.

Jim Malkin lives in Chilmark.