Having had the privilege of helming the Californian, a top sail schooner, during a blow off San Diego (yes water running down the decks, seas 15-25 feet), I can say that even these boats don't go to weather very well. Tacking is an exercise in patience and practice. You must fall off a point or two to pick up speed and then time it just right to put the helm over. To complete the tack the boat must start about 7 or 8 points off the wind and then carry all the way through to the the same point on the new heading. Only then can you harden up to somewhere around 6 points. to finish that trip we actually got caught off shore San Diego and spent almost 4 hours trying to get into the harbor due to minimal engine assist and wind blowing directly out the harbor mouth.
One of my most fun sailing adventures even though it wasn't on my boat.
One of my most fun sailing adventures even though it wasn't on my boat.