As often as I can.
But when I know that's what kind of day or occasion it will be, I generally start out with a milder smoke and work my way up in strength and intensity as the day goes on. That way I don't burn out my taste buds to the point that I can't taste anything.
Planning that strategy and sticking to that plan is tough at times, especially at a herf where all of us are gifting & trading cigars. Here I'll be smoking a Padron 1964 natural as my first mild cigar of the day and someone hands me a stick that I've never smoked before...and it's a tasty Nicaraguan powerhouse...inpatients soon sets in. As Steinbeck wrote, "the best laid schemes of mice & men often go awry."