
Modern weather forecasting is so good that we aren’t often caught out, but we all take a chance once in a while, especially when we’re under pressure to be somewhere else. Coastal sailing in near-gale conditions isn’t the same as ocean storm survival. Instead, we have to think hard about possible shelter and local dangers. Different boats have varying abilities. So do crews. Here’s a hypothetical scenario with three boats facing the same dilemma. They start together, heading for the same destination, but end up in three different places.
It is before dawn one day in August and three boats are anchored in Fort Pond Bay, just inside Montauk Point on Long Island, New York. They have something in common. They’re each manned by male crews who have agreed to meet their wives on Martha’s Vineyard the following morning. This means the pressure’s on, big-time.
Our guys haven’t left themselves much in the way of slack. They’ve around 70 miles to make good to Vineyard Haven via Block Island and Vineyard Sound, but they’re experienced and they don’t mind a few night hours if that’s what it takes. Besides, the forecast looks almost perfect, with 15 knots of breeze out of the south nicely abaft the beam. There’s a front hanging around out to sea, but the forecast implies that this will stay put, at least until the following night. The weatherman hints that the dirty stuff may make its move early, but the boys are optimists. Besides, they’re in a deep hole if they don’t arrive, so there’s only one decision: Go for it, and soon!
The boats
The three boats are very different. The smallest is Tiny Tot, a light displacement, a 22-foot sloop with a lifting keel and an outboard engine. Her sailing performance is better than average for her size. Her two crew are young and fit and are experienced racing sailors.
Next up comes Minnie in the Middle, a 35-foot charter boat, with big cabins, a huge freezer, a powerful engine and sails like flour bags. To be kind to her crew, they are healthy middle-aged guys, but they spend most of their year earning their keep in offices and don’t trouble their personal trainers too often. They’ve been ashore the night before celebrating the last of their freedom and are somewhat the worse for wear.
The final yacht is Big Bopper. She’s a 45-foot S&S-designed cruiser-racer from the Golden Age of seaworthiness, the mid-1970s. Her skipper is a tough egg in his fifties (he’s the one with the wife most likely to hammer his credit card) and the crew are his son and son-in-law. All are veterans of several Bermuda races.
Passage plan
Big Bopper is confident he’ll make Vineyard Haven in one shot. With this breeze he might manage to carry his asymmetric, but even if the angle’s too shy, he’ll manage the best part of 7 knots on the reach. He should be in by Happy Hour, and he hasn’t given much thought to what might happen if it should turn rough.
Minnie in the Middle also hopes to be in by dark, or at least before bedtime. Because of the prevalence of an east-going stream, so long as they catch the early tide past Montauk Point, they’re in with a good chance of a push-up Vineyard Sound at the other end. If it wasn’t for the ladies, they’d have stopped for another night on the tiles in Block Island. But it’s not to be.
Tiny Tot is more concerned about the weather. Being small, her crew have considered the options of Block Island or even a run for Newport if the front arrives early and backs the wind to the southeast. They have given little consideration, however, to contingency plans for heading off the retail therapy session if they don’t show up in time. To get the full benefit of the tide rips, they are going to be first to leave.
In case the breeze should back, all the boats wisely opt to get upwind by going south around Block Island.

The action and the bad news
Tiny Tot heaves in her light anchor, pops her cruising chute and whizzes off into the rising sun just as Minnie’s boys are putting the coffee on. By the time she’s east-southeast of Block, Minnie is in sight and slowly narrowing the gap, perhaps motorsailing. The Bopper is hammering up fast, well heeled over, with a bone in her teeth. They’re 30 miles out now, and the radio issues a new forecast. It isn’t what any of them want to hear.
Block Island Sound and Martha’s Vineyard are expecting the front early—in the next two hours in fact, with winds backing southeasterly and increasing to 35 knots, gusting to 45—a whole gale, with rain and poor visibility. The front is forecast to take four hours or more to pass through, after which the wind will veer southwesterly and drop to 20 knots.
Already, the sea is showing signs of building and the cloud is thickening dramatically. Aboard Big Bopper, the barometer has fallen 0.18 inches in the previous two hours, so there’s no doubting what’s coming. The boys are out of luck.
The options
Here are three boats, all confronting what on the face of things is the same situation, but because of what they are and who is on board, their dilemmas are very different. All are under pressure to continue, but the conditions, as forecast and backed up by observation, will be more than uncomfortable; they are potentially dangerous. The water is not deep and the seas will lump up rapidly, possibly becoming steep enough to cause a knockdown. The boats are going to have to work to weather to make their destination, and it has to be said that their ability to do this varies enormously. Here’s what each crew made of its situation.
Tiny Tot
The breeze is already heading Tiny Tot as the boys shape up to decision time. One thing’s obvious. There’s no way they can press on into a potential 40 knots of wind. They aren’t powerful enough. Their outboard engine will be out of the water as much as it’s in, and submitting a 22-footer to what could easily end up as a 15-foot beam sea just to meet your wife on time is madness. The Tot must change her plan, pronto.
Block Island is closest, but to get there she must take the rising sea on the beam. The entrance to Great Salt Pond is narrow too, and if the wind has backed she’ll be going dead into it. Her crew decides to head for Newport, 25 miles to the north. That way, they’re running away from the weather and delaying its arrival.
The entrance to Newport is easy, even downwind, and they’ll be doing what their boat likes best. She virtually planes, given a good helmsman and the right conditions. She’s got both now. They square away onto a broad reach and scorch off into the scud. On the way, one of the boys plots a double-checked GPS waypoint in the middle of the entrance. As visibility cuts down, they steer for this, checking log and course carefully as a backup.
The front arrives when they’re 8 miles out. They douse the main, gybe and run in under jib, making shelter an hour later. Then it’s into the Black Pearl for a bite and a well-earned stiffener, four hours of sleep, and then back out again at midnight in a decreasing sea, a southwest breeze and bright stars. They carry their spinnaker most of the way and arrive just in time to meet the better halves of their relationships who have just arrived on the Vineyard ferry.
Minnie in the Middle
It never occurs to Minnie’s crew to head for Newport. In truth, it wouldn’t have been such a sound option for them anyway. They aren’t feeling too good; in fact, one is horribly seasick already. With their furling 150 percent genoa, there is no way they are going to make the Vineyard without motorsailing. They wisely realize that although it seems strong, they do not know how the engine would behave under pressure.
Perhaps the tanks are dirty. A long motorsail in heavy going would stir them up and stop the engine for sure. Better not take the chance. Instead, they decide to keep the engine in reserve. It has plenty of power, so the Block Island entrance wouldn’t hold the sort of horrors it did for Tiny Tot. They decide to turn round and nip into the Salt Pond. They’re anchored just as the first big gusts come hammering over the island.
Unfortunately for Minnie’s crew, once they have the hook well dug in, they can’t resist going ashore to celebrate their salvation. They have a frightening time of it clambering back on board from the dinghy in a gale of wind and lashing rain. No one fancies putting back to sea when the wind eases, so they spend the night in their bunks instead. They finally make the Vineyard the following afternoon. Alas, they are too late. As they tie up, the bags of designer clothing are piled on the dock alongside the black looks.
Big Bopper
No prizes for guessing what she does. A well-found boat of her description was born for this sort of thing. The crew won’t enjoy bashing on, but the boat won’t mind a bit. Her skipper also knows that if the weather guys are wrong and more wind turns up than she can handle, all he has to do is douse his headsail completely, triple-reef the main, start his well-maintained engine and steer up into the seas at slow ahead.
This old fishing boat survival method works every time, so long as you’ve got the power to keep the head up to the seas. The vital thing is not to fall beam-on and risk being rolled. The Bopper can do this all day if she has to. She won’t run out of fuel because the front will pass in a few hours, and the knowledge that she has this technique up her sleeve gives her crew total confidence.
As it turns out, she doesn’t have to do this, and she arrives in Vineyard Haven in time for a late supper. All hands enjoy the sleep of the just and the skipper gets up to take Tiny Tot’s lines as the coffee’s brewing. His wife is still on the mainland waiting for the ferry.
I don’t know what you think after assessing the situation these captains faced. We reckon all their choices were sound, even though one got in trouble with his wife. The fact that only two of them made it, and in wildly different ways, shows that boats vary as much as the people that crew them. The important thing is to understand your own ship, not to ask more of her or her crew than they have to give and to stay quietly off the statistics lists. – T.C.