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The First Five Cigars

Updated 2026-08-28 · by Eric

This is the order I'd hand someone starting out, and every cigar on it is one I bought, smoked, and rated here. It's a progression, not a top five. Each slot teaches one thing, and the pick is the cigar on my shelf that teaches it best.

The list starts mild and forgiving, steps up body and complexity one lesson at a time, and ends at a benchmark, so that by cigar five the words on every review page (strength vs body vs flavor) map to something already felt. Smoke them a few days apart rather than five in a week. The palate needs time to file each lesson (how to taste a cigar).

One disclosure before the picks, because it changes how you should read this page. Nothing here got in on reputation, which means the list is limited by what I've actually smoked and written up. Where my shelf doesn't have a clean fit for a slot, I say so and name the closest thing instead of reaching for a famous band I've never reviewed. No slot goes to a cigar I rated below Five-Pack (3/4).

Cigar one: the forgiving start

A first cigar should be mild, short enough to actually finish, and gentle enough with nicotine that nothing about the hour turns unpleasant (nicotine, and not getting sick). A robusto, call it an hour, is the right size for it (which size, when).

Smooth and mild-to-medium, built around creamy bread notes and a light sweetness, and it never punished me for smoking it on an empty stomach. That's exactly the safety margin a first cigar wants. It also cost about ten dollars, which is the other thing a first cigar wants.

What to notice: the sweetness that hangs around between puffs, and the retrohale. This one's mild enough to push a little smoke through your nose without paying for it, which makes it the right place to learn the technique. Fair warning, the draw runs snug.

Cigar two: the one-gear lesson

Before complexity means anything, you need to meet its opposite... a cigar that tastes in the fifth inch exactly like it tasted in the first. This slot also stretches the clock, because a toro runs closer to ninety minutes.

Mild to mild-plus with essentially one gear. Light spice on the retrohale, tobacco sweetness throughout, a little earth late, and it wants coffee next to it rather than bourbon.

What to notice: that "not complex" is a real category and not an insult. This is also the place to learn burn management, because I got two full thirds out of mine doing nothing but rotating the slow side down, then a couple of touch-ups late (cigar troubleshooting).

Where my shelf still stretches, and what I'd take instead if I could. An ideal cigar two would step up slightly in body from cigar one. This one consolidates the mild ground instead of climbing, because the next rung up on my shelf jumps straight to medium. I've since reviewed two mild-plus cigars that rate a 3/4 and would fit the lesson better, and neither one can have the slot: the Dunbarton LecheBurra runs $19.45 and sells at exactly one online retailer, and the Punch Reserve Collection is discontinued and I couldn't find it in stock anywhere. A cigar you can't walk in and buy is no use on a list like this. So the slot stays where it is, labeled for what it is, until something you can actually buy earns it.

Cigar three: technique changes the flavor

The lesson here is that smoking is an input, not just an output. Pace, puff size, and how much you retrohale all change what a cigar tastes like.

This is the closest a cigar has come to my top tier without earning it. A single puff, a double puff, a half retrohale and a full one each gave me a different flavor... bready, sweet, nutty, earthy, baking spice, black pepper, coffee, in different combinations.

What to notice: run the experiment on purpose. Single puff, wait, double puff, compare. The bitterness I found in the back half rode the double puffs and the ash, so slow down and knock the ash off and it recedes (why does my cigar taste bitter). Eat a real meal first. This one creeps up late.

Cigar four: the wrapper lesson

Proof that the wrapper isn't decoration. This is where maduro shows up, and with it the idea that one leaf can redirect an entire blend.

Sweet, chocolatey, nutty, with the spice moving around enough to hold my attention and a final third that never turned on me. The first top-tier verdict on this list.

What to notice: the transitions. Track how the spice, sweetness, and nuttiness trade places across the thirds. This is the cigar where "it changes as it burns" stops being an abstraction.

And then there's the control experiment I didn't plan on. Same line, same twelve-year aging program, different wrapper:

That one's here as a caution, not a pick. Same factory, same tobacco program, opposite verdicts. Wrapper matters.

Cigar five: the benchmark

A full-flavored, complex cigar that shows you the upper end, and becomes the reference point everything else gets measured against.

Nearly two hours of baking spice turning to pepper, milk chocolate flashing to dark, almond, leather, dark coffee, and a sweet linger that would not quit. There was more going on in it than I could name at the time.

What to notice: how much the retrohale controls the spice, how the profile keeps moving, and how a dip in the final third can recover. Full dinner first, water alongside, no schedule. This is the cigar the first four were practice for.

Two famous names I'd skip as starters

Both are fine cigars, and both landed mid-tier with me. Not worth buying new, not worth refusing if somebody hands you one.

The Padrón is the band a beginner reaches for first, and I found it one-dimensional. Padrón never goes on sale, so there's no deal to redeem it later. The Davidoff is the price trap: a pleasant, thin-smoking background cigar at money that should buy a great deal more.

After the five

The natural sixth, and a graduation cigar rather than a starter. Medium-plus to full, dark chocolate and deep sweetness, and a torpedo head that punishes a careless cut. Worth knowing that the stick I reviewed behaved a little tamer than this blend usually does.

A solid alternate for the medium rungs, with one catch: the Toro I reviewed is no longer in the current lineup, so plan on shopping its sibling sizes.

Buy them as singles

The five above run somewhere around $55 to $65 at street prices, and you should buy them as singles, not boxes or five-packs. A local shop can sell you exactly one of each, properly stored and ready to smoke tonight. Online orders need a week or two of rest after they ship (how to buy cigars). The box comes later, after a blend has earned it twice.

You need almost nothing to smoke these. A cutter, a lighter, and somewhere to keep them (the gear that actually matters).