ASA and PSIA Instructor
Join Date: Apr 2000
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Practically speaking you cannot tip over a keel boat like a Cat32 with white sails. If the boat heels excessively, it will automatically turn towards the wind, overwhelming any effort you could make to maintain let alone increase, the heel angle.
Over 20 degrees or so of heel, most boats start to experience increasing sideslip so progress upwind is actually reduced by the excessive heel.
If you really go looking for trouble...large sea action or an out-of-control spinnaker can lay a keel boat over, or even roll one, but for most production boats like Catalina, the boat's inherent stability will roll it back...
Certified...in several regards...