I've come across a few boats recently that, while they had tempting layouts and nice equipment lists, seemed to be sorely lacking in their ability to make real progress to windward.
Here on the Great Lakes, that's a deal breaker.
There are few, if any, one-way passages here. The lakes aren't big enough to exploit global weather patterns, the way you might on an Atlantic Circuit — south from Europe, catch the trade winds to the Caribbean, north to New England, and then skirting the Azores High to reach the British Isles, keeping the wind largely at your back most of the time. No, if you're on the Great Lakes, two-thirds of all your sailing will be close-hauled.
And I do mean *close* hauled. We sail Maverick V right on the edge of luffing more often than on any other point of sail. I'm always fiddling with sheet leads to try to eke out a few more degrees of pointing ability.
Lots of other places are like this, too. And, even on a mostly downwind route, the ability to make progress to windward can open up a special destination you might have missed. Or it can get you into a comfortable port with a well-stocked bar (the tavern kind) rather than being stuck outside a bar (the sand kind) overnight. Or it can save the boat from disaster when the engine fails as the barometer is dropping, the wind is shifting, and a rocky shore is looking awfully close.
It baffles me that anyone would intentionally design a sailboat with poor windward ability in this day and age. Yet we see it all the time. Big charter cruising cats — condomarans, as we sometimes call them — carrying canvas-enclosed fly bridges above deck saloon cabins, yielding so much windage that, without the twin diesels, their windward ability would be eclipsed by that of an 18th century brigantine. Fat monohulls decked out with cockpit enclosures, solar-panel-festooned arches, and dinghies in davits, piling drag and leeway onto a boat that, from the start, was optimized more for dockside amenities than for sailing performance.
If you're thinking of designing, building, or outfitting a boat like this, please give some serious thought to what your priorities should be.
Rigs and sails, and the underwater foils to balance them, are expensive. They take a lot of work to maintain. They limit your access to a lot of interesting places.
If the design criteria for a particular boat are such that it's just not going to sail well to windward, and will rely on its engine when the apparent wind is less than 60–70° off the bow, you should consider omitting the rig entirely. A motorboat is nothing to be ashamed of, and if designed from a standpoint of efficiency — rather than of piling as much volume and marked-up equipment as possible into a given length — can be much cheaper to run than a sailboat under engine.
On the other hand, if sailing is important at all, you owe it to yourself (as owner-skipper) or to your client (as designer) to put your foot down and insist on good performance to windward. Don't accept ten compromises that each cut "just a degree or two" off the tacking angles. Don't pile on excess windage in the form of loaded-up arches and bulky cockpit enclosures. Don't mess up the pitch and roll moments of inertia with excessive weight in the forepeak, lazarette, or upper rig.
And, if you do make those compromises, be honest with yourself and with your clients about it.