Matching cigars to anything is very individual. There cannot be any strict or hard rules when it comes to cigar smoking. But we can offer some advice anyway.
Aperitif cigar has to be small and mild. It is assumed that the supper is to come and the taste buds are not irritated yet. You have to feel lightness, freshness. A strong cigar does not suit light drinks which are usually offered as aperitifs. It may be interesting to combine a light or medium cigar with Champagne though this alliance is rather disputable. Champagne gives purity, freshness, lightness and passes these qualities to a cigar. Cigar has to be smoked for 15-30 minutes. Small-sized cigars usually do not contain ligero leaves and thus, are not very strong. We can recommend small format cigars such as Hoyo de Monterrey, La Gloria Cubana or Regios of Saint Luis Rey line.
Thus, aperitif's main function is to create the feeling of lightness, freshness, to prepare taste buds and not to take too much time.
To choose a cigar for digestive is a bit harder. The aim of a digestive drink is to reveal cigar's flavor, enhance it and, sometimes, to hide the flaws. Most big and medium-sized cigars match well with hard drinks such as Cognac, rum, whisky, Armagnac.
It is preferable to have Cognac of X.O. level, not less. For example, Martell X.O reveals flowery, vanilla notes and suits medium-format cigars. Courvoisier X.O adds fruity, chocolate nuances and suits big-sized cigars. Remy Martin X.O has vanilla and oak flavors which makes it suitable for medium-strength or strong cigars. Race of Hennessy X.O represents all kinds of flavors - flowers, dried fruit, raisins, nuts, chocolate. It suits well large-format cigars.
Armagnac is stronger than Cognac, it requires stronger, rougher large-sized cigars such as Bolivar, Partagas. In this case Armagnac gives all its sweetness (caramel, vanilla) and creates a very interesting aftertaste. Calvados matches such cigars as Romeo y Julieta Churchill.
To choose a cigar for gastronomy is a new trend very popular nowadays. Most advanced gourmets are looking for triple alliance: food+alcohol+cigar. This trend however has a lot of adversaries who believe that it is impossible to try all three components at once and that cigars are smoked before or after lunch. But in France they organize several testings where they try to do all these things at the same time and it turns out to be rather successful. If a cigar can be complemented with alcohol, why not choose some third element which can help the cigar to open completely or add some missing qualities to it. All three components have to complement each other, not to block. Alcohol reveals cigar's flavor and food intensifies and accentuates it.
When should you start smoking? Some suggest the time right after meal ordering so that you can smoke first third of a cigar. Others recommend smoking a cigar right after meal when the sensations are still fresh.
Fish and meat suit well medium-sized and large-sized cigars. Fish has to be roasted or grilled. Creamy sauces based on red wine but without sour cream, rather rich, can be added as well. Fowl requires cigars of a simpler taste as well as sauces based on wine with truffle or vanilla taste. Stews or veal in sauce suit Montecristo No. 2.
As for the desserts one has to remember the combination of four Cs: coffee, Cognac, chocolate and cigar. It is not recommended to match cigar and milk-based meals including cheese. Ice-cream and sherbets do not match cigars also because they are cold. Red berries and fruits do not allow the flavor to reveal itself in the mouth, either.
All alcohol-based desserts (or those with alcohol-based sauces) can be accompanied by a corresponding cigar. For example, there is a menu consisting of cream-caramel with spice, honey, whisky and chocolate combined with Partagas Lusitania. Combination of a cigar and a sweet fruit such as dates and honey-, nut- or chocolate-based sauces can also be very successful.
Here are some more variants of menu: Foie gras with cacao and nut sauce and toast roll with El Rey del Mundo Choix Supreme and 40-years Porto. Smoked salmon with pear sauce and Montecristo No.2 cigar and single malt whisky. Ravioli with shrimp and Eastern ginger sauce matched with Juan Lopes No. 1 cigar and red wine. Rack of lamb with curry sauce and Romeo y Julieta Churchill and semisweet wine.