The Best Way to Spend Your $100 on Cigars in Cuba

Credit: Ernesto Mastrascusa / Getty Images

Buying Cuban cigars just got a little easier thanks to a widening of travel privileges by the folks at the Capitol. More than 50 years after the last ones were imported, you can now bring $100 worth of Cuban cigars into the country for yourself.

You'll be surprised what $100 can (or can’t) buy you. Even though all of the cigars made in Cuba are technically owned and distributed by the country itself, prices still vary by brand, so the same amount of tobacco will cost one price for a Cohiba and another for Romeo y Julieta.

Cigar prices are going to vary a bit, and since the conversion rates change it's not going to be an exact science. But whether you're stocking up for the long haul or trying to impress your less lucky friends, this will help you map out how to burn your cash.

The Value Buyer
Let's say this trip to Cuba is a one-time deal for you. You're hoping to stock up just long enough to ride out the last of the embargo, which you're pretty sure won't outlast your self control. There's a small but delicious smoke for you: the Rafael Gonzalez Perla. Yes, it's a tiny cigar – just a few inches, quite narrow. But think of these little guys as a snack. The main course is coming, eventually.

Expect to Bring Back: 20+

The Traditionalist
You'll never go wrong with the Montecristo No. 2. One of the truly classic Cuban cigars, this pointed pick is a name-brand buy that (usually) manages to live up to the hype. Montecristo, though still a few years short of a century old, quickly outran most of its competitor during the capitalist days of the Cuban industry, and locked in legend status during the Revolution. The standardized No. 2 vitola (another word for size) exists in most of the Cuban cigar lines — or at least did at one point or another — so you'll see it in other brands. You'll also find something called the Petit No. 2: a smaller version of the same cigar, which will be slightly less expensive. That's a good option for the same taste at a lower price.

Expect to Bring Back: 5-8

The Orator
Are you always the life of the party? Do you have quippy replies to cocktail party snark, a library full of your own books, and the power to unite people? No? Well, you can always pretend you do with the classic Churchill. A long-lasting, large-format cigar, the Romeo y Julieta Churchill is an oft-imitated size meant to be gripped firmly in one's jaw or, alternately, pointed accusingly at others while in the hand. At least that's how you've seen it in the movies. Like Winston's own legacy, this one has stood the test of time, and its name has certainly stayed recognizable through the years.

Expect to Bring Back: 5-7

The Brand Name Shopper
Cohiba, right? You're just here for Cohiba, aren't you? Look, Cohiba is great, don't get us wrong, while other brands owned by the Cuban government have suffered in tough times, they've always kept Castro's "private" label at the highest possible quality because: 1) It’s the best seller and 2) you don't piss off Castro. But the price has also tended to reflect those facts, meaning that you'll be paying more by volume for a Cohiba than any other line. Still not dissuaded? The three most reliable and tasty vitolas tend to be the short and stubby Robusto, the long and narrow Lancero, or the Churchill-like Esplendido. Feel free to mix and match with some of the smaller Siglo I and II cigars to get your last few dollars spent.

Expect to Bring Back: 3-6

The Historian
If you want to get technical, the last Cuban cigars acquired legally in the U.S. were rounded up by Kennedy's press secretary in 1962. Kennedy's man came back with 1,200 machine-made H. Upmann Petit Upmanns and, stockpile secured, he signed the embargo into law. The Petit Upmann was discontinued in 2002, but the better-made Petit Corona is a nice, short substitute for any sentimentalist.

Expect to Bring Back: 15+

The Collector
The thing about Cuban cigars is that the more obscure stuff tends to go out of production. While Montecristo and Cohiba production increases, the likes of Diplomaticos and Quai D’Orsay dwindle in range and volume. Diplomaticos, in fact, is down to just one size: the torpedo-tipped No. 2. No, it's not a recognized brand, but in the days of small batches and micro breweries, this of this as the under-appreciated gem in the portfolio. And one that some may never get to try, at this rate.

Expect to Bring Back: 10+

The True Connoisseur
If you're truly a cigar obsessee, then frankly you've been purchasing illegally for quite some time, so the idea of buying from Cuba seems expensive and hassle-filled. Well that's not entirely true. Cuban prices don't just avoid the import taxes and retail prices (and luxury taxes) of nanny states like Australia and Canada, where the'’re basically trying to price people out of bad habits. And besides the savings, there are some things that never make it to the U.S., like Edición Limitadas and regional editions for other countries. A lot of stuff never gets exported, and a lot of discontinued cigars are still on shelves in Cuba, aging away, waiting for the right guy to come along. Are you that guy? Be that guy.

The All-Day Smoker
There are cigars that make for an entire day of smoking — the kind you light on the first tee and finish at the clubhouse, or take out when the boat pulls away from the dock and pose with while holding the day's catch. These aren't the sorts of smokes that one accepts lightly: It’s not just an investment, it’s a challenge — one that will be rewarded by attention and determination. Though they've fallen out of fashion, Cuba still makes two of the most legendary long smokes: the Partagás Lusitania and the Hoyo de Monterrey Double Corona. These are multi-hour smokes, so though they're a little pricey, they're giving you your money's worth.

Expect to Bring Back: 4-5

The Best Friend
You're the generous type, but only with people who appreciate a good thing. And you don't like spending a lot of money unless you get to share it with someone special. If this is you, we seriously suggest you focus on yourself for a moment — but if you insist, there's only one cigar line you'll be purchasing: Cohiba Behike. Released in extremely limited quantities every year, the three Behike vitolas make rare appearances because of the special blend of tobaccos, and the company's desire to maintain a large demand. The largest size is the 6 1/2 inch BHK 56, the smallest the 4 1/2 inch BHK 52. There's argument over which of the three is the "best" but they're all at a higher quality level worthy of a special occasion. This guy owes you. Big.

Expect to Bring Back: 2