Cigar and Whiskey Pairing: One Cigar for Every Bottle on Your Shelf

A good cigar and whiskey pairing rests on one decision: the cigar should be about as strong as what is in the glass. Get that right and the flavors mostly look after themselves. This guide gives one cigar to each kind of bottle, and most of them come from a single shelf: the seven cigars of El Septimo's Sacred Arts Collection, each named for a painter, which run from medium to full and cover bourbon, rye, Scotch, Irish and Japanese whisky between them.

We keep all seven as singles and in boxes of 20, next to Davidoff, Cohiba, Byron, Alfonso and Atabey. So every pairing below names a first pick and a second one from another house. Each cigar is linked, and the cards show the live price and stock. If you would rather answer four questions and be handed a cigar, the Cigar Finder does exactly that.

Two rules do most of the work

Match the weight first. A barrel-proof bourbon flattens a mild cigar. A full-bodied maduro buries a light Irish whiskey. Put light with light and heavy with heavy and you are most of the way there.

Then pick a direction. You can echo the whiskey, sweet with sweet or spice with spice. Or you can set it against something different, the way a smoky Scotch sits next to dark cocoa. Both work. Echo is the easier place to start.

One more thing before the chart: pour less than you think. A cigar outlasts a drink by a wide margin, and our guide to how long each size lasts will help you plan the evening around it.

The cigar and whiskey pairing chart

Six kinds of bottle, two cigars for each. The first pick is the one we would hand you. The second is there if you want a different house or a different direction.

In the glass	What it tastes like	Our pick	Also good
Bourbon	Vanilla, caramel, sweet oak	El Septimo Salvador Dali Toro	Cohiba Black Gigante
Rye	Pepper, baking spice, a drier finish	El Septimo Da Vinci Lancero	Cohiba Nicaragua Robusto
Sherried single malt Scotch	Dried fruit, toffee, nuts	Davidoff Winston Churchill Late Hour	Byron Petit Poemas
Peated single malt Scotch	Smoke, brine, char	El Septimo Michelangelo Robusto Extra	El Septimo Botticelli Salomon
Irish or Japanese whisky	Light, soft, honey and orchard fruit	El Septimo Rembrandt Torpedo	Cohiba Connecticut Toro
The old bottle you have been saving	Deep oak and a long finish	El Septimo Van Gogh Royal Salomon	Alfonso Extra Añejo No. 4

The six first picks, one for each bottle. Choose a single or the box on the card. Prices and stock are live.

Bourbon and cigar pairing: sweet meets sweet

Bourbon is the sweet one. It is made mostly from corn and aged in new charred oak, and that is where the vanilla, the caramel and the toasted wood come from. It wants a cigar with a little sweetness of its own.

Our pick is the El Septimo Salvador Dali Toro, a 6½ x 54 at medium strength. We taste sweet coffee, a cherry finish, something bready, a touch of vanilla and dark chocolate late in the smoke. Beside bourbon the vanilla lines up and the cherry reads like the fruit in the glass. A single is $25.00, and the Salvador Dali box of 20 is $500.00.

If you would rather have contrast, go darker. The Cohiba Black Gigante is a 6 x 60 under a Connecticut Broadleaf wrapper, full in body, all espresso, dark chocolate and toasted cedar. It turns a sweet bourbon into dessert with coffee, and it has the size to stand up to a barrel-proof pour. More of the line sits in our Cohiba collection.

Rye: answer spice with spice

Rye is bourbon's drier cousin. Less sugar, more pepper, a little baking spice. Match it.

The El Septimo Da Vinci Lancero is long and slim at 7½ x 40 and medium in strength. The narrow shape concentrates the flavor: black pepper and cocoa powder over oak, a hint of anise, an earthy middle and a soft coffee finish. The pepper in the cigar meets the pepper in the glass. The Da Vinci Lancero box of 20 is $520.00.

The second pick is the Cohiba Nicaragua Robusto, a 5 x 52 made entirely of Nicaraguan tobacco. It is medium to full, with earth, pepper, dark cocoa and toasted wood, and each cigar is sealed in a glass tube. The box holds eight.

Cigar and Scotch pairing: sherry casks and peat are two different jobs

Scotch is really two drinks when a cigar is involved, so we split it.

Sherried single malt

Malts aged in sherry casks, many of them from Speyside and the Highlands, taste of dried fruit, toffee and nuts. One cigar on our shelves was built around a whisky cask. In the Davidoff Winston Churchill Late Hour, one of the filler tobaccos spends six months in casks that once held Speyside single malt. You can taste it: oak, leather, dark chocolate, black coffee and a clear note of malt.

Ours is the Petit Panetela, a 4 x 38 that comes five to a tin. It is full in body and short, which makes it right for one pour after dinner. The Late Hour tin of five is $51.00, and the rest of the house is in our Davidoff collection.

For something rounder, the Byron Petit Poemas is a 4 x 50 that tastes of sweet cherry, figs, raisin and warm caramel. That is close to a description of a sherry cask. And for the curious, there is a second cask cigar here: El Septimo Spain Rioja includes tobacco aged in Rioja wine barrels. Try it beside a Scotch finished in wine casks.

Peated single malt

Islay malts and other peated whiskies bring smoke, brine and char. A mild cigar simply disappears next to them. The El Septimo Michelangelo Robusto Extra is the full-bodied one in the Sacred Arts line: a 5½ x 50 with layered earth, natural tobacco, spice and a long finish. Earth and peat sit well together. The Michelangelo box of 20 is $360.00.

If you would rather soften the smoke than meet it, the El Septimo Botticelli Salomon does that. It is a 7½ x 58 with espresso, earth, cocoa, aged leather and dark wood, and the cocoa takes the edge off the peat.

Irish and Japanese whisky: keep the cigar quiet

Irish whiskey is light and soft, and much of it is distilled three times. Japanese whisky tends to be delicate and is often poured long, over ice with soda. Both are easy to overpower.

The El Septimo Rembrandt Torpedo is the gentle one. It is a 7 x 54 at medium strength: creamy, with cedar, light wood, a little sweetness and a mild spice at the end. Nothing in it shouts over the glass. The Rembrandt box of 20 is $520.00.

The second pick is the Cohiba Connecticut Toro, a 6 x 50 under an Ecuadorian Connecticut Shade wrapper. It is mild to medium, with cream, cedar, almond and light coffee.

That leaves one painter. For blended Scotch, or any whisky with soda, the El Septimo Raphael Toro is a 6 x 50 with earth, cedar, a little spice and a creamy finish. It gives a tall, cold drink something to stand next to.

The old bottle: give it time

Some bottles have waited a long while. An 18-year-old single malt. A bourbon someone gave you that you have not opened. They deserve a cigar that takes its time too.

The El Septimo Van Gogh Royal Salomon is nine inches long, the longest cigar in the collection at 9 x 55. It is medium to full, with dark cocoa, leather and aromatic spice, and it burns slowly and evenly. An old whisky changes in the glass over an evening, and this cigar is still going when it does. The Van Gogh box of 20 is $800.00.

Age also sits well with age. The Alfonso Extra Añejo No. 4 is aged five years on cedar and French oak, and it tastes of both: cedar, French oak, cream, vanilla and toasted nut, in a mild to medium 6¾ x 56. The Atabey Benditos rests at least five years in cedar-lined rooms and comes out a medium 7¼ x 58 with sweet cedar, dark fruit, caramel and soft leather. Either one beside an old Scotch is two long waits ending at the same table. You will find the rest of each house in Alfonso and Atabey.

The second picks, from Cohiba, Byron, Alfonso and Atabey. Prices and stock are live.

At the table: how to drink and smoke at the same pace

The pairing is decided before you sit down. A few habits make it work once you do.

• Light the cigar first. Let it settle for a few minutes, then take the first sip.
• Take turns. Sip, wait a moment, then draw. The two should meet on your palate, one after the other.
• Add water before you add ice. A few drops open up a strong pour. Ice chills the whiskey and quiets it, which suits a highball and shortchanges an old single malt.
• Keep a glass of plain water nearby. A mouthful now and then keeps both tasting like themselves.
• Do not dip the cigar in the whiskey. It wets the wrapper, the head goes soft and the cigar burns unevenly. The glass and the cigar belong side by side.

The right objects help. The El Septimo Cigar Whiskey Glass is a 200 ml double old fashioned with a cigar rest built into the glass, so the drink and the cigar share one hand. It is $25.50, with the logo on the side or on the bottom, and both live in our whiskey glasses collection.

On the bar itself, the Brizard and Co. Gatsby table lighter stays put, lights with a triple torch flame and has a punch built in. It is $240.00 in whisky calf leather and black. The Alfonso Añejo ashtray gives the cigar a proper place to rest, and the rest of our ashtrays are worth a look if the table is a gift in itself. For the cut, the Brizard V Cutter makes a clean wedge and comes with its own leather pouch. Our cutter and lighter guide explains what the money buys in each.

And when the pairing has to travel, the Brizard Havana Traveler with flask carries five cigars in a cedar-lined case and a 6 oz flask in one leather folio, with pouches for a lighter and a cutter. It is $550.00.

The table, set: two glasses, a lighter, an ashtray, a cutter and the traveler. Prices and stock are live.

Sacred Arts is one line among many. We list more than a hundred El Septimo cigars and accessories, and the full El Septimo collection is the place to keep going. If you want to taste before you commit to a box, our cigar samplers are built for that.

The short version

Match the strength of the cigar to the strength of the pour, then decide whether to echo the whiskey or contrast it. Bourbon takes the Salvador Dali. Rye takes the Da Vinci Lancero. Sherried Scotch takes the Davidoff Late Hour, peated Scotch takes the Michelangelo, Irish and Japanese whisky take the Rembrandt, and the old bottle gets the Van Gogh. Pour small, take turns, and keep the cigar out of the glass.