I'm on three meds to regulate it now. I was put on two immediately upon diagnosis and a 3rd when it didn't come down far enough. The third was a beta blocker and it brought my BP down into good normal levels and as a nice side effect, essentially cured my headaches.
I have the same family history as you. Parents and grandparents all had terrible high blood pressure and were all medicated. My maternal grandmother was one of the healthiest people you'd ever meet- she was only 5'3 tall and never weight more than 110 lbs her whole life. Exercised regularly. There were no processed sugar treats in her house- she was the quintessential healthy farmers wife. Her blood pressure was always super high. Meds were the only option.
I'm not in great shape but I'm not terribly over weight. My quality of life has improved so much since getting my BP regulated that it is more than worth it being on the proper meds to keep it in check.
I can literally feel it when my BP spikes- it sucks. I feel awful. Just get the medical help you need.