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Pairing beer and cigars involves finding complementary flavors and profiles that enhance each other to improve the overall sensory experience. I wrote a more detailed guide that covers generally how you should pair beer and cigars. It's definitely worth a read if you want to learn more about this.
Stouts are known for their rich, roasty, and sometimes sweet flavors, often featuring notes of chocolate, coffee, and caramel, so when selecting a cigar to pair with a stout, it is generally recommended to choose cigars that can match the stout's intensity and richness. Medium to full-bodied cigars with flavors of dark chocolate, earthiness, or spice can provide an excellent counterpoint to the deep flavors of stouts.
Below are 5 specific recommendations for pairing relatively easy to find stouts with relatively easy to find cigars.
The intense flavors of dark chocolate, espresso, and molasses in the stout pair harmoniously with the complex and full-bodied character of the Padron 1964 Anniversary Series Exclusivo.
The velvety mouthfeel and mild sweetness of the Milk Stout pair well with the rich and chocolatey flavors of the Perdomo 20th Anniversary Maduro Robusto.
The bold and roasty characteristics of the Narwhal Imperial Stout complement the nutty and cedar notes of the Ashton Symmetry Robusto.
The smooth and rich flavors of the Obsidian Stout pair well with the dark chocolate and spice notes of the My Father Le Bijou 1922 Petit Robusto.
The robust and complex flavors of the Old Rasputin Stout complement the medium-bodied and balanced profile of the Arturo Fuente Gran Reserva Double Chateau Fuente.
Cheers, and long ashes!