Most first cigars go wrong before the first real puff. The cut is too deep and the wrapper unravels, or the foot gets charred on one side and the cigar burns crooked for an hour. Both are avoidable, and both are worth explaining to the table before anyone lights up.
The cut
A premium cigar is sealed at the head with a cap, a small round of wrapper leaf glued in place. You are removing just enough of that cap to open the draw. Find the shoulder, the point where the rounded head starts to curve, and cut above it. Cut past the shoulder and the wrapper has nothing holding it, so it starts to peel.
A straight (guillotine) cutter is the default and works on almost any cigar. Cut in one quick, firm motion; hesitating crushes the head. A punch bores a small hole in the cap. It keeps the head intact but can feel restrictive on thick cigars. A V-cutter makes a wedge notch, a middle ground between the two. For a party, one decent double-blade guillotine is all you need.
The toast
Toasting means warming the foot, the open end, before you actually draw through it. Hold the cigar at an angle with the foot just above the flame, not in it, and rotate slowly until the whole face of the foot glows evenly at the edges. Skip this and the cigar lights unevenly, and an uneven start usually means a crooked burn.
The light
Use a butane torch, a soft-flame butane lighter, cedar spills, or wooden matches. If you use matches, let the head burn off before it touches the cigar so you taste wood and not sulfur. Avoid gasoline lighters and scented candles; the fuel taste carries straight into the smoke.
Put the cigar to your lips, hold the flame just off the foot, and draw gently while rotating. When the foot is lit all the way around, take it out of your mouth and blow softly on the ember to check that it glows evenly.
Smoking it at a party pace
Cigar smoke is tasted in the mouth, not inhaled. A puff every minute or so keeps it lit without overheating it, and an overheated cigar turns bitter. Let the ash fall on its own instead of tapping it every few minutes; a longer ash helps the cigar burn cooler. If it goes out, blow gently through it to clear stale smoke, then relight the same way. When you are done, set it down in the ashtray and let it go out on its own. Don't stub it out.
Our Cigar & Whisky Journey kit builds the whole night around one cigar per guest, with a whisky poured at each third. For what to pour, start with cigar wrappers and whisky styles.