Good rum is easier to find than a great cigar...
If you're in the US, you'll almost never go wrong with any Padron. Their 1964 Aniversario might be the best selling cigar in the country. Stick with a smaller ring gauge (no larger than 52 max) and that's only because the Torpedo is a 52. I like the smoother natural wrapper especially with a sweet spirit like aged rum, but most like the sweeter, darker maduro, when they're drinking a single malt scotch.
Beyond Padron, it gets very tricky and has a lot more to do with personal taste and whether or not the cigar has been aged at least a year w/o the plastic wrap on it, after it has been rolled, which is extremely difficult to find.
No, I'm not a Padron rep. They're the only cigar company that doesn't have reps...They don't need them. ;-)
If the rum is aged and sweet and syrupy, I've liked the spicier tobacco from Nicaragua (like Padron), which happens to be putting out the best cigars in the world over the past 10 years or so and particularly the last 5 years. Other great cigars from Nicaragua that pair well with aged rum are as follows:
Drew Estate #9 (belicoso)
Drew Estate Herrera Esteli (belicoso)
Oliva Melanio (Torpedo or Figurado)
Oliva Master Blend III (torpedo or robusto)
Pepin Garcia/My Father - Flor De Las Antillas (belicoso)
Cabaiguan Guapo (corona gorda)
L'Atelier LAT (Lancero, Torpedo or 38 Special)
If you want even more pepper still:
Padron 1926 #2
Drew Estate T52
The Honduran Alec Bradley Prensado and Family Blend are also worth mentioning. Both tend to be less peppery than one from Nicaragua.
As a general rule, I've noticed that the short list of quality Dominican Puros and the best Cuban cigars go well with rums like Brugal 1888 and DonQ Anejo.
As a general rule, I would steer clear of cigar brands made by "walmart" companies Altadis and General Cigar. These are mostly Cuban brand names (Cohiba, Montecristo, Partagas, Punch, etc...) that are not made in Cuba and made for quantity, not necessarily quality. You'll be paying for a Cuban brand name and its not even made in Cuba or even the same company. Also, even if it is rolled in Cuba, doesn't mean its a quality cigar.
That's probably more info than you were looking for, but I hope it helps.
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