Cigar Buying Guide 101

Celebrate the art of a hand-crafted cigar.

Article Updated

Sometimes, a cigar is just a cigar. And sometimes, it’s a work of art. 

Cigars have retained a resilient following, remaining a favorite vice of the wealthy and discriminating. The inaccessibility of Habanos, or Havana cigars, continues to perpetuate the mystique, and nothing tops the boxes of hand-rolled cigars that bear the phrase “hecho a mano”—made by hand.

A Rich History
In the early Americas, tobacco was considered so valuable, it served as currency, was smoked as a peace offering and used by native medicine men for shamanic ceremonies. The United States’ founding fathers created a tradition of cigar culture in private salons—early cigar lounges that housed the fragrant smokes. Since the Cuban embargo imposed by President Kennedy in 1962, a resilient industry by Cuban exiles—who survived their revolution and prospered despite invasive federal regulation—has succeeded through several decades.

Shown above: Camacho Corojo
Considered one of the most unique cigars available, the blend is a 1997 Vintage Jamastran Valley Corojo wrapper and includes genuine, first generation Cuban seed. This nostalgic hand-crafted Honduran has a hint of cocoa. Although still managed by the Eiroa family, Oettinger Davidoff acquired this company in 2008.
Wrapper, Binder and Filler: Authentic Corojo
Format: Nacionales
Length: 5½ inches
Ring Gauge: 44
Strength: Full

Since as early as 1931, Hollywood has used the cigar as a prop and accessory. In the silent movie classic “City Lights,” Charlie Chaplin played an endearing tramp who struggled through lighting a cigar. Fellow funnyman Groucho Marx was never seen without a stick in his hand—flicking it right, left, up and down, but never dropping a single ash. Even James Bond femme fatale Xenia Onatopp, portrayed in “Golden Eye” by Famke Janssen, punctuated her sentences with a gran panetela. Not once did she blink from the smoke or flinch from the draw—a remarkable portrayal of self-control, or perhaps just pure enjoyment. And, she only lit her cigar once. Milton Berle, George C. Scott, and George Burns top the long list of thespian cigar aficionados.

Shown ablove: Davidoff Aniversario Series
Based in Geneva, Davidoff has been credited with creating the cigar cellar and setting a European benchmark for quality since 1906. There are three formats in the Aniversario Series: Grand Double Corona (No.1), Churchill (No. 2), and the Toro (No. 3). Since Grand Double Corona and Churchill are mild, they are good choices for cigar novices, while the Toro is robusto.
Origin: Dominican Republic
Wrapper: Criollo
Format: Dominican
Size: 8 2/3 inches, 7 inches and 6 inches
Ring Gauge: 48 and 50

There is of also, of course, the nemesis of the Habanos, Fidel Castro, alongside one of the most famous statesmen in history, Winston Churchill. Churchill inadvertently became a poster boy for the Cuban cigar and was rewarded with a format created in his honor. 

But the great orator never shied away from his love of cigars, as he informed a visiting Saudi Arabian king: “As I was the host at the luncheon I raised the matter at once, and said to the interpreter that if it was the religion of His Majesty to deprive himself of smoking and alcohol I must point out that my rule of life prescribed as an absolutely sacred rite smoking cigars and also the drinking of alcohol before, after and if need be during all meals and in the intervals between them. The king graciously accepted the position.”

Exclusive Puffs

Cigars may be a part of our collective history, but tastes may have changes over the years. 

“Unlike the past, today’s customer is not loyal to brands but seeks the latest trend,” said Charlie Hennegan, proprietor of Liberty Tobacco Lounge. 

However, an entrepreneurial full service cigar bar called Elite Mobile Cigars is on the move in San Diego. Elite caters to special events and exclusive parties of international following, and its list of clientele reads like a Who’s Who in the sports, financial and movie industries, as well as the political arena. CEO and connoisseur Dave Harry purchases very rare humidors, stocked with equally rare cigars of which only 30 sets are made for the first of each year.

Shown above: Arturo Fuente Opus X Lost City
Due to its limited production, this cigar is a rare jewel, with its true format is the rumination of many cigar forums. It was the first Dominican puro—containing only tobaccos grown in the Dominican Republic—on the market. This hand-rolled special edition was grown for and named “The Lost City,” a movie directed by actor Andy Garcia as a historical tribute to the revolution in 1958 Havana.
Origin, Wrapper, Binder and Filler: Dominican Republic
Size: 7.5 inches
Ring Gauge: 38
Strength: Full

“I have been collecting these cigar sets since 2006 and have had them only on display,” said Harry, who carries an estimated $1.8 million retail in rare cigars. “I am a true collector of cigars because I keep what I collect and wait till there are no more available.” 

Harry also trades with other collectors who no longer have the passion to store cigars. In addition, his connections with different families like the Fuentes, the Padrons and the Garcias allow Harry to obtain “special cigars that are not sold in the typical market.” 

For example, one of Harry’s most unique cigars is the Princessa D, which is only one of the cigars in the Fuente Opus X 2008 Charity Box, of which only 500 boxes are made each year.


Shown above Ashton ESG
Developed to celebrate the anniversary of 20 years of dedication and collaboration between Robert Levin and Carlos Fuente, Jr., the wrapper for this cigar was grown at the prestigious Chateau de la Fuente in the Dominican Republic. Flavors are roasted peanuts and almonds ending with sweetness.
Origin, Binder and Filler: Dominican Republic
Wrapper: DR Sun Grown Rosado
Format: Robusto
Size: 5 1/4 inches
Ring Gauge: 52
Strength: Full


“The Opus Princessa D has over 14 different types of tobacco in it, which makes the cigar change flavor from draw to draw,” Harry explained. “And I do like to smoke cigars, not just look at them.” 

Harry said the most popular brands requested are the Arturo Fuente Opus X or a Cuban Cohiba.

“A lot of people ask for those only because they are illegal in the U.S. and like the fact they have something they shouldn’t,” Harry admitted. “I believe the Cuban market is not what it used to be. In my opinion, there are a lot of very good cigars that are legal in the U.S. which are better.”

Selecting a Cigar

Selecting the perfect smoke can seem daunting, especially to a novice. Thankfully, we’ve got some tips to allow you to boldly go where you may not have gone before. “Selecting a cigar is by trial and error, similar to wine tasting or trying out new brews,” Hennegan said.

In a cigar, the outermost wrapper determines much of the cigar’s character and flavor, while the filler—wrapped up bunches of leaves inside the wrapper, held together by binders—makes up the majority of the cigar. The size and shape of the cigar, together are known as the vitola, is measured by length and ring gauge. Also key in choosing a smoke is strength, which should not be confused with flavor. Strength is similar to coffee—strong, mild, etc.—while flavor evolves or deepens on the palate as tobacco is drawn upon, often resembling fruit, spices, flowers or even leather.

Shown above: Armada
A full-bodied cigar hand-rolled with a rare Ecuadorian Sumatra maduro wrapper fermented from a single leaf of ligero, the Armada is the most limited of the Man O’ War line, with only 10,000 cigars made each year. This cigar was developed by Abdel “AJ” Fernandez, a protégé of Don Alejandro Robaina—the man considered the “Godfather” of tobacco. Fernandez moved to Nicaragua to produce his own cigars after studying in Cuba under Robaina.
Origin, Binder and Filler: Nicaragua
Wrapper: Ecuadorian Sumatra Maduro
Format: Corona
Size: 6.5 inches
Ring Gauge: 56


“At some point you have to make a decision and run with it, but always remember, what is mild to one person is not so to the next,” Hennegan advised. When choosing a full-bodied cigar or smoking for the first time, Harry offers this advice: “Be sure to have a good meal and don’t try something new on an empty stomach. Also, only puff on the cigar and hold it in the mouth. More experienced smokers will hold the smoke in and let the last 20 percent out through their noses. This gives the cigar its true flavor profiles while using all your senses.”

Shown above: Gurkha Beauty
Under the British regime in India, legendary Nepalese fighters grew their own tobacco and rolled it into cigars, which the British called “gurkhas.” A premium brand, Gurkha has been in business for 125 years, and in 1989, Kaizad Hansotia assumed ownership after discovering this Far East legend in Goa, India. The Gurkha Beauty is medium-bodied with a grassy flavor.
Wrapper: Ecuadorian
Binder: Dominican Republic
Filler: Nicaraguan
Length: 6.5 inches
Ring: 58


For Panamanian resident and ex-pat Robert Cozza, a cigar aficionado of 60 years, the best smoke is “a Honduran full-bodied Maduro Torpedo because it has flavor, consistent draw and an even burn. I can light it with one matchstick. Cigar quality and consistency from bundle to bundle is disappointing.  I don’t believe the leaf is aged as of days of yore.”  

Padilla Signature 1932
The Padilla Signature 1932 is a limited production produced by Ernesto Padilla to honor the birth year of his father, Heberto Padilla. Handmade in Don Pepin Garcia’s El Rey de los Habanos Factory, this starts out mild and creamy, eventually becoming full.
Origin: Miami
Wrapper: Nicaraguan Corojo
Filler: Nicaraguan Corojo and Criollo
Binder: Criollo
Size: 6.8 inches
Ring Gauge: 42


Although veterans like Cozza are old school with their matchsticks, according to Harry, “A good cigar will burn very slowly and will allow you to come back later and not have to relight it.  This is a sign of a well-constructed cigar.”

Top Choices

A well-made cigar should provide about two hours of enjoyment, and we have suggestions in these pages for wiling away the hours:
Camacho Corojo

  • Davidoff Aniversario Series
  • Arturo Fuente Opus X Lost City
  • Ashton ESG
  • Armada
  • Gurkha Beauty
  • Padilla Signature 1932
  • Macanudo Vintage 2000
  • La Aurora Preferidos

No matter which cigar you choose, Hennegan has some last sage advice: “The most important thing to remember when smoking, is it’s an enjoyment, much like a cocktail at happy hour. Relax, take your time, slow down. Smoke with a friend or friends if possible. The cigar is a social vehicle—the shared smoking experience is bonding.”

Shown above: Macanudo Vintage 2000
This smoke is from the Connecticut Valley in the United States, which produced one of its finest crops this century. General Cigar had the foresight to put a great deal of this leaf away for extra aging. Prior to this debut, Macanudo has only released five editions of the vintage line since 1979. It is hand-crafted and medium-bodied, becoming full.
Origin: Dominican Republic
Wrapper: Connecticut Shade (2004)
Filler: Dominican Piloto Cubano
Binder: Mexican San Andreas (Medio Tiempo)
Size: 5½ inches
Ring Gauge: 50


And nothing brings people together better than a hand-crafted work of art. Formats—or cigar shapes—have changed and evolved through the years, but the tradition of hand rolling remains intact despite technological advances. Machines cannot mimic quality and fool the sophisticated palate.  Touching real pages in a book by a fireplace or smoking a fragrant hand-rolled Habana or Nicaraguan vitola defies current trends.

La Aurora Preferidos
La Aurora Preferidos are available with a number of different wrappers, each with a unique taste to each particular line. The Red Maduro, Platinum Cameroon and Gold Corojo cigars receive extra aging in oak barrels, resulting in a flavorful woodiness. Sapphires have Connecticut wrappers that have been aged for five years in rum barrels.
Origin: Dominican Republic
Wrapper: Eight-year Brazilian Matafino
Filler: Piloto Cubano (DR), Bahía and Cameroon
Binder: Piloto Cubano
Format: Lancero
Size: 6 ¾ inches
Ring Gauge: 40


Enjoying respites, sunsets and celebrations is an unshakeable tradition for human nature.  Baroness Dudevant, best known by her nom de plume as French literary George Sand, captures this pastime in one eloquent sentence: “The cigar is a perfect compliment to an elegant lifestyle.” 

Looking for a Smoke?

Pick up the finest cigars at these local spots.

Elite Mobile Cigars

Liberty Tobacco Lounge
2650 Via De La Valle, Del Mar
7341 Clairmont Mesa Boulevard, San Diego

Habanos Café & Cigar Lounge
3111 Hancock Street, San Diego

Cuban Cigar Factory
551 Fifth Ave., San Diego