Being an Italian American, espresso has become more than just coffee, it is almost a spiritual experience.  Your typical American Starbucks drinker doesn’t truly understand what espresso even is.  Espresso is not a type of bean, but in fact, it is a process of making the coffee.  Espresso is made by forcing extremely hot water through finely-ground coffee.

The result is a powerful, rich “shot” of espresso. Due to the smaller size but higher concentration, you get a higher caffeine count and therefore a stronger cup.  I like two sugars in my espresso, so when pairing a cigar I want something strong, rich, bold and sweet.

I went with the Foundation Tabernacle, a “wise” choice if you get my joke*.   The dark, broadleaf wrapper adds in notes of espresso, milk chocolate, and a bold, rich sweetness.  The strength is also on par with the espresso, so it will help you get through the rest of your day.

The macchiato has gained some popularity in the US over the past few years due to its prevalence at coffee shops.  However, most of these are covered in caramel sauce or somehow involve pumpkin.

A true macchiato consists of two shots of espresso in a cup followed by a drop of steamed milk and a dash of foam on top.  This results in a combination of the rich, strong espresso that combines with a smooth, creamy flavor for the best of both worlds.

The words creamy and smooth were really important when choosing a cigar, and it resulted in me picking the perfect one.  The brand new Sobremesa Brulee from Dunbarton is smooth, mellow and creamy with notes of nuts, coffee, and vanilla.  It’s the perfect morning pairing for the coffee and cigar nut.

Cappuccino is probably the most well-known beverage on this list, at least in terms of fancier coffee drinks.  The weird part is, it is essentially the same drink as a macchiato.

However, it uses more milk and it’s then topped with some cinnamon and or a dusting of chocolate.  This adds in some sweet flavors and makes it more visually appealing.

Due to the combination of rich, creamy, sweet and bold flavors, choosing the cigar for this pairing took a bit of time.  However, I finally landed on the Crowned Heads Le Careme and man did it work perfectly.  The Connecticut broadleaf wrapper gives it those rich and sweet notes, while its Sumatran binder adds in touches of nuts and coffee.

The Nicaraguan filler tobacco gives it an earthy and spicy center, giving you a complex cigar and coffee experience.

While the actual Mocha beverage is not something you generally see millennials ordering at the local shop, the use of Mocha as a flavoring has become quite popular.  This time of year, a Mocha is actually one of my favorite beverages.

It is essentially a combination of cappuccino and some hot chocolate, similar to a Dunkaccino but just better.  This gives you that caffeine jolt and coffee flavor along with the rich chocolate notes from the hot chocolate.

For this pairing, I went back to my first ever Maduro cigar and the cigar that made me fall in love with broadleaf tobacco.  The Ashton Aged Maduro taught me that a dark cigar can actually be smooth and mellow.

This Fuente creation offers up rich chocolate and coffee notes thanks to the broadleaf wrapper as well as a smooth, creamy and nutty center with the Dominican filler tobaccos.  This is a great choice if you just love a mix of rich, robust and sweet flavors.

I actually find the concept of American coffee to be quite hilarious.  This is because it can be used to describe two different varieties.  In the US, an Americana is made using the drip technique and typically needs to be mixed with milk, cream, or sugar in order to have any taste to it.  This is the typical coffee you make at home or get at a diner.

In Italy, if you order an Americana, they just take a shot of espresso, followed by 2/3 cups of just hot water.  Essentially, they are calling us weak, and they aren’t wrong.

The typical Americana coffee is a medium roast, usually with cream and or sugar.  This creates a balanced, slightly sweet and slightly creamy blend.  For this pairing, I went for balanced, smooth and creamy, and I found it in the Montecristo White Series.

Its luscious Ecuadorian wrapper sits upon aged Dominican tobaccos giving it that perfect balance of nutty, creamy and smooth.