Light ’er Up

Cooler weather, lavish holiday dinners, and chest-warming cocktails (perfectly punctuated with a fine smoke) all herald the coming of cigar season. Here’s what you need to keep puffing in style.

Every man who is serious about cigars should smoke these five superior stogies. Ultra-premium and standing the test of time, they rank among the best in the world. Score the Cubans while vacationing anywhere outside the U.S.— and don’t worry about “accidentally” leaving a few in your suitcase for the flight home. Hey, it happens!

Cohiba Siglo VI

For many, Cohiba is synonymous with the Cuban cigar, and the Siglo VI arguably represents Cohiba at its most ambitious, luscious, and alluring. The Siglo line debuted in 1992, commemorating Columbus’ discovery of Cuba in 1492. Subsequently, Siglos I through V each represented a century since the momentous event. This latest iteration, introduced in 2002, manages to be ultra-rich yet incredibly smooth. It’s an unmatched wonder of tobacco blending that towers over nearly every other smoke. (Call it the Puff Daddy, if you must.) []

Tobacco: Cuban

Ring Gauge: 52 

Length: 5 5/6 inches 

Montecristo No. 2 

When a cigar is created in 1935 and remains one of Cuba’s best-selling smokes nearly 80 years later, you know it’s something special. Torpedo-shaped, full-bodied, and intensely flavorful, this cigar provides the ideal finish to an  epic meal. Look for the label bearing a simple white-on-brown fleur-de-lis. []

Tobacco: Cuban

Ring Gauge: 52 

Length: 6 1/8 inches

Davidoff Aniversario No. 1 

The first in an elite series of cigars, the Aniversario No. 1 is medium-bodied with rich flavors that remain consistent throughout the smoke. As soon as you slide it free of its handsome wooden tube, you’ll be able to enjoy the easy draw and take in this grand double corona’s woody aroma. []

Tobacco: Dominican 

Ring Gauge: 48

Length: 8  2/3 inches

Partagás Series E No. 2 

This stone-cold Cuban classic made a splash in 2011 with its notable heft, impressive girth, and formidable flavor. The E is definitely not for guys who want to blend into the background. Light one up and enjoy instant baller status. []

Tobacco: Cuban 

Ring Gauge: 54 

Length: 5 1/2 inches 

Padrón Anniversary Series 1964 Diplomatico Maduro

Celebrated cigar company Padrón debuted this stogie to universal acclaim in 1994 to celebrate its 30th anniversary. Exuding a pleasing, complex mix of smooth flavor notes, it smokes as well today as it did when Pulp Fiction was in theaters. []

Tobacco: Nicaraguan

Ring Gauge: 50 

Length: 7 inches 

PRO TIP: You’re not lighting a cigarette, so don’t use a standard lighter and don’t press a match directly onto the tobacco. Instead, advises Mauricio Cordoba, general manager of Club Macanudo in Manhattan, toast the wrapper’s front tip with the flame from a wooden match or torch lighter, Puff a few times, and it might spark up from there. If not, gently put the flame to the cigar at a 45-degree angle and draw on it; that should do the trick.

Photos by Terry O’Neill / Getty Images