Pairing Cigars & Alcohol – Penfolds Grandfather Rare Tawny

Pairing Cigars & Alcohol – Penfolds Grandfather Rare Tawny
Date: November 2023
Author: Inspector X

Cigars and alcohol. Two luxury products that go hand in hand, and sometimes even meet on business level. Aging tobacco in whisky, rum, or cognac barrels is a practice several brands do to achieve extra flavour to the wrapper for certain lines. The famous bourbon brand Maker’s Mark has their own cigar, sold in tubes with the signature wax coating. Drew Estate works with Pappy van Winkle and used to make Kahlua cigars. Mombacho used to have the Diplomatico series. General Cigars works with Sazerac, which resulted in Fireball cigars, Weller by Cohiba and collaborations with Buffalo Trace. And there is the Diesel Whisky Row, a collaboration with Rabbit Hole Distilleries. Fratello Cigars also sells craft beer. Most famous are probably the Cuban collaboration between Martell Cognac and Cohiba. Dominique London, the European retailer with more than 20 shops in the UK, Belgium, Switzerland and the Canary Islands takes it one step further. They bought a distillery in Wales and produce whisky, gin, rum, vodka and liquors.

Penfolds Grandfather Rare Tawny

In 1844, Christopher and Mary Penfold officially established their vineyard at Magill Estate in Australia. Where Christopher was also a doctor, Mary was in control of the vineyard and she was very successful. After Mary’s retirement, Georgina Penfold, the daughter of Christopher and Mary, took control over the company and in the early 1900s, Penfolds was the largest winery in Australia and producing about one third of all the wines made in Australia. Penfolds is still a huge name, not just in Australia but also in the rest of the world, with both affordable wines and high-end wines selling for hundreds of euros (or more, in high-end restaurants).

When the Penfold’s started the vineyard, the initial idea was to make fortified wines such as port and sherry. The Penfolds Grandfather Rare Tawny is a tribute to that start in 1844. The port is made with tawnies matured in oak casks for 14 years, and then being introduced to the solera system for an additional six years. James Halliday, Australia’s most important wine critic, has given this port a 97 score on several occasions. The port has an ABV of 19.5% and is made with a blend of Cabernet Sauvignon, Shiraz/Syrah, and Mourvèdre grapes.

As for my personal relationship with port, every time that I drink port, I love it and say to myself “I need to drink more port” but then I hardly ever do. I don’t know why. It is such an underrated drink, not just by me but by a large part of the population. Port deserves a bigger audience, but I should lead by example and order some more port today as well.


I poured a bit of the port in a wine glass. The aroma is quite spicy and fruity with raisins, liquorice, roasted nuts and fruitcake. The port tastes like liquid raisin, vanilla, oak and fruit. There is plenty of sweetness with a hint of white pepper. The sweetness is all fruit, including pear. The flavours are complex and intense. This is a high end port and it shows. Due to the sweetness, I would pair this with a medium bodied cigar from Nicaragua without any sweetness. No maduro wrapper for sure. Maybe a Perdomo Lot 23 Sun Grown, A.J. Fernandez Dorado or a My Father Flor de Las Antillas.

Black Cup

Port isn’t the first spirit that comes to mind when you think cocktails, but there are a few cocktails made with the fortified wine. I never had one, but I’m always open to new things and so I made this black cup. An easy cocktail with a few simple ingredients that every cocktail enthusiasts must have at home. Due to the amount of ice and soda water there isn’t much happening on the nose. The strawberry flavour shines through, with that typical mouthfeel of soda water. The lemon creates a sour backdrop for the fruitiness of the port to shine, but in a muted way. This is a very refreshing cocktail, but honestly, next time I would not use such a high-end port for this cocktail. Since this is a friendly, mellow cocktail I would pick a mellow cigar with this. Hoyo de Monterrey Epicure #2 for example, or a Quesada Reserva with its smooth Connecticut wrapper. Maybe even a sweet Sobremesa Brulee.

And now for the Black Cup recipe:

1 strawberry (I use a slightly defrosted frozen strawberry)

2 ounces or 60ml of Penfolds Grandfather port
½ ounce or 15ml of simple syrup
½ ounce or 15ml of lemon juice, freshly squeezed
Club Soda (can be replaced with a lemon-lime soda of choice)
Muddle the strawberry in a cocktail shaker with the simple syrup. Then add the lemon juice and the port. Shake with ice and strain into an ice-filled Collins glass. Top up with a splash of soda. You can garnish this with a cucumber wheel but that is optional.

Valentino’s Delight

I’m not the biggest fan of spirit forward cocktails, but I do like cocktails with coffee. So this cocktail could co both ways. It looks thick and creamy. There is no ethanol on the nose, there is coffee with nutmeg and cream. There is a slight resemblance to Baileys on the nose. The alcohol flavour of the Jack Daniels is quite dominant with a nice creamy mouthfeel, with coffee and chocolate. The port is completely lost in this mix. This tastes like a spiked chocolate drink, sweet and creamy. A Connecticut Shade cigar would go very well with this.

And now for the Valentino’s delight recipe:

¾ ounce or 22½ml of Bourbon (I used Jack Daniels)

½ ounce or 15ml of Penfolds Grandfather port
½ ounce or15ml of Marsette Monsoon coffee liqueur
¾ ounce of 22½ml of double cream

Garnish: ground nutmeg
Fill a cocktail shaker with ice and add the liquids. Shake vigourusly and then strain into a chilled Martini glass. Garnish with a sprinkle of ground nutmeg.

Port Lemonade

With lemonade you expect a bright yellow drink but due to the port this drink is more a cloudy amber cocktail. There is a mild liquorice aroma from the port. This is a confusing cocktail as all ingredients are equally detectable. The tardiness of the lemonade, the booziness of the vodka and the raising and liquorice of the port. It is well balanced, and it will go well with a lot of cigars. Something with a Habano or Corojo wrapper. Maybe a Jas Sum Kral Toothpick Habano or a West Tampa Black. A Maestranza from Meerapfel can be a nice pairing too.

And now for the Port Lemonade recipe:

1 ounces or 30ml of Penfolds Grandfather port
1 ounce or 30ml of Ybet Vodka
2 ounces of 60ml of lemonade

½ ounce or 15ml of simple syrup.
Add all the ingredients in a cocktail shaker with ice and shake. Strain into a Collins glass over fresh ice.

Homemade lemonade recipe:
1 cup of (caster)sugar

1 cup of water

1 cup of lemon juice
boil the water with the sugar until the sugar dissolves. Once it’s all dissolved, add the lemon juice and the simple syrup in a pitcher. Add 2 to 3 cups of cold water and a few slices of lemon. Stir and enjoy.

 Inspector X

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