I have sailed on a cat of similar size and design as the Alpha - (a 38' with stub keels). We tried to sail upwind from Granada to Carricou. The same day an Atlantic 42 headed the same direction, and a 40+ Catana. I wasn't pleased with our progress, particularly when I noticed a heavy open gaff rigged workboat, towing a skiff, was easily beating me. All three cats ended up motoring most of the distance and I'm not sure any of them beat the gaffer.

A collection of race results proves that a very performance oriented cat (like Gunboat) will not quite keep up with a performance oriented monohull upwind, but the difference is small. However in races like the Heineken regatta, the cruising cats similar to the Alpha are not even allowed to sail the same course as the cruising monohulls, because they do not stand a chance of finishing in the same day.

Certainly there are cats that can go upwind pretty well as the recent ACup proved, and there are plenty of very slow traditional monohulls. I'm not sure which I would bet on if a heavy cruising cat with stub keels like the Alpha were put against a Westail 32, but against any more modern monohull upwind, it would be no contest in any conditions. Comparing the Alpha 42 to say a J-133, it is considerably heavier, has far more windage, and no effective lateral plane. The J will be faster on every point of sail in all conditions. This is not speculation, but very supportable by race results, passage times, etc.