Last Christmas we brought you ‘5 Whiskies That Taste Like Christmas (and the Perfect Cigars to Pair Them With)‘. It featured five glorious whisky expressions that essentially tasted like Christmas in a glass to us.

As a bonus detail, we provided 5 test-driven premium hand-rolled cigars to pair with each.

This year, we continue this yuletide tradition by mixing up 5 Cocktails That Taste like Christmas; cocktails with that contain relatively easy-to-find ingredients, aren’t too complicated to make, and are sure to impress around the holiday season. To further assist you, we’ve included information on suitable substitute ingredients.

Once again, we couldn’t resist including a perfect robust cigar to pair with each.

So, mix up one of these sumptuous cocktails, grab a cigar, and cozy up by the fire, for after a few of these festive libations, visions of sugar plums are sure to be dancing in your head.

Orange Chocolate Espresso Martini

The name says it all.

For many of us, the Christmas season awakens thoughts of gorging on Terry’s Chocolates; a foil-wrapped chocolate ball that you smack against a hard surface to break open to release individual slices. Once an English creation, Terry’s is now made in Strasbourg, France. This cocktail was crafted with this Christmastime chocolate gift in mind.

Throw in some coffee notes and you’ve got the perfect rich and robust cocktail to pair with a splendid maduro wrapper cigar.

Pair the Orange Chocolate Espresso Martini cocktail with the Oliva Serie V Melanio Maduro Figurado cigar. According to Cigar Aficionado Magazine, the Melanio Maduro “shows a luxurious procession of rich, regal character starting with notes of German chocolate cake that segue into a smoke of baking spices, malted chocolate and lively, cedary accents”.

  • Cocktail ingredients:

    1 1/2 oz Absolute Orange Vodka

    1/2 oz Creme de cacao

    1/2 oz Dillon’s Coffee Liqueur

    1 shot of espresso coffee

  • Instructions:

    Shake all ingredients with ice for 25 seconds and fine strain into a coupe glass. 

Glass: Chilled coupe

Garnish: Coffee beans and/or an orange slice

Pair with: Oliva Serie V Melanio Maduro Figurado

Gingerbread Old Fashioned

What’s better than a fresh out of the oven gingerbread man, man? A gingerbread man-flavored cocktail of course!

This little number is a festive riff on the world’s first official cocktail, the Old Fashioned.

100% rye whisky delivers notes of spice that balance out the sweetness brought forth by the Salted Caramel Crown Royal and the ginger liqueur. A few dashes of chocolate bitters ties everything together nicely with a big bow.

Pair the Gingerbread Old Fashioned cocktail with a Flor de las Antillas cigar by My Father. The true medium-bodied Flor de las Antillas delivers a delightful array of flavors, including prominent notes of cocoa, pepper, sweet cedar, and earth.

  • Cocktail ingredients:

    1 1/4 oz Lot 40 Dark Oak 100% Rye Whisky (or any 100% rye whisky)

    3/4 oz Crown Royal Salted Caramel Whisky

    1/4 oz Domaine de Canton Ginger Liqueur 

    3 dashes Kinsip Chocolate Bitters (plain ol’ Angostura will work fine if need be)

  • Instructions:

    Stir all ingredients in a mixing glass half filled with ice and strain over a large ice cube. 

Glass: Double Old Fashioned Glass 

Garnish: Orange zest

Pair with: Flor de Las Antillas Robusto by My Father

Canadian Christmas Coffee

Canadian riff on an Irish coffee with some candy cane notes tossed in for good measure.

What’s not to love?

This is the second cocktail on our list to contain coffee, because we know darn well that so many cigars lovers love to pair a cigar with their coffee.

Pair a Canadian Christmas Coffee with the La Galera 1936 Box Pressed cigar. The blend of the 1936 is medium to full in body, with a ton of great flavor, exhibiting notes of cocoa, pepper, dried fruit, espresso, and earth, which results in a satisfying complexity.

  • Cocktail ingredients:

    1/4 cup chilled heavy cream

    1 1/4 oz Forty Creek Barrel Select Canadian Whisky (or any blended Canadian whisky)

    1/4 oz Peppermint Mocha Kahlua

    1 teaspoon granulated sugar

    3/4 cup of strong coffee

  • Instructions:

    Whip or froth heavy cream with sugar until it has stiff peaks. Pour whisky and peppermint Mocha Kahlua into a mug and add add coffee. Spoon out whipped cream on surface.

Glass: Glass coffee mug

Garnish: Ground cinnamon

Pair with: La Galera 1936 Box Pressed

Maple Gin Flip

Somewhat similar to Egg Nog, a flip-style cocktail is a cocktail made with a spirit, whole egg, cream, and a sugar source.

They can be served hot or cold.

This decadent foamy cocktail is a Christmastime delight and is real simple to make, which means that after you try this out on one of your gests, it’ll be easy to continue making them when the others hear about how delicious it is.

As an added bonus, its cooling foamy texture serves to cool the heat of your cigar.

Pair the Maple Gin Flip with the E.P. Carrillo Encore Majestic; a robusto-sized cigar of immaculately detailed flavor that ranges from oak and tea to caramel sweetness with tangy citrus pops of candied orange peel. It’s elegant, refined and nuanced from first puff to last.

  • Cocktail ingredients:

    2 oz Dillon’s Dry Gin 7

    1 oz Cream

    1 egg, separated

    1/4 oz Maple syrup (bonus points for sourcing a whisky barrel-aged maple syrup)

  • Instructions:

    Place ingredients in shaker with no ice and shake for 10 seconds. Open shaker and add ice. Shake for 20 seconds and strain into chilled coupe or Nick & Nora glass. Grate nutmeg as garnish.

Glass: Chilled Coupe or Nick & Nora

Garnish: Fresh grated nutmeg

Pair with: E.P. Carrillo Encore Majestic

Spiced Rum Maple Old Fashioned

Canya tell we like our maple syrup? Well, we are Canadians after all.

Another Old Fashioned Riff, this sumptuous little creation melds the slightly sweet spice notes of a spiced rum with the “funky” pot still essence of a Jamaican rum. Maple syrup sweetness and some bitters round things out.

Pair the Maple Spiced Rum Old Fashioned with the My Father Le Bijou 1922 Box-Pressed Torpedo; a rich, full-bodied treat in typical My Father form. Featuring a Habano Oscuro wrapper and a healthy mix of Nicaraguan long-fillers, Le Bijou 1922 exudes a robust array of flavors delivered in a remarkably smooth fashion.

  • Cocktail ingredients:

    1 oz Island Diaz Spiced Rum

    1 oz Smith & Cross Jamaican Rum (or Appleton Estate 12 Year)

    1/4 oz Demerara Simple Syrup

    1/4 oz Maple syrup (bonus points for sourcing a whisky barrel-aged maple syrup)

    3 dashes Angostura Bitters

  • Instructions:

    Stir all ingredients in a mixing glass half filled with ice and strain over a large ice cube. Garnish with an orange zest and a brandied cherry.

Glass: Old Fashioned

Garnish: Orange zest & brandied cherry

Pair with: My Father Le Bijou 1922 Box-Pressed Torpedo

Bonus: Cognac & Rum Hot Toddy

A warming cocktail such as the Cognac & Rum Toddy will be of great assistance when obligated to smoke a cigar in a less-than-ideal environment like a cold garage or shed.

This winter warmer blends the robust character of a pot still rum with the elegance and dark fruit character of a cognac. If you’re pairing this with a larger-sized cigar, skip the conventional tea mug serve it in a double-walled insulated mug like a Yeti to keep it hot for a much longer period of time.

Pair the Cognac & Rum Hot Toddy with a Casa Magna Connecticut cigar. Known for being traditionally mild, this Connecticut cigar is a medium-nearing-full-bodied treasure delivers on notes of subtle sweet cedar, toast, earth and pepper.

  • Cocktail ingredients:

    1 oz Jamaican rum (we use Appleton Estate 12 Year)

    1 oz Cognac (a brandy works too)

    1 oz Lemon juice

    3/4 oz Maple syrup (bonus points for sourcing a whisky barrel-aged maple syrup)

    3 dashes of Angostura bitters

  • Instructions:

    Add all ingredients to 3 ounces of boiling water in a mug. Garnish with a cinnamon stick and lemon wheel.

Glass: Glass tea mug or insulated mug/tumbler

Garnish: Cinnamon stick and a lemon wheel

Pair with: Casa Magna Connecticut