First 27.7 should be a pretty good upwind performer. We used to race
a lot against a certain First 31.7 and she did it pretty well upwind, way too well for our taste...
For me, this sounds like a rigging
problem. As Pete7 suggested, it’s a good idea to check that mast is not leaning to one side. You also want to check that the mast is straight and not curved to port or starboard or even both. On our racing
boat, we have a pretty complicated Bergrstöm&Ridder rig with seven individual shrouds on each side. It’s a lot of work to get everything right: rake, pre-bend, straight mast, and equal tension.
We also once had an issue with keel
causing similar problems. We grounded just slightly and checked the keel
only. After tuning the rig endlessly for nothing, we finally found out, that the bulb had got loose just enough so that it had been able to turn about 5 degrees to port. For some reason, the offset did not cause such problems when reaching and running. I do not recall
, if the lifting keel on 27.7 has a bulb or not, however, you might want to check the keel as well.