When it comes to smoking cigars in the winter, it’s a tradition to choose small cigars over their larger, time-consuming cousins. Luckily, smaller cigars usually cost less, affording us an opportunity to stack the deck with premium favorites!
Of course, cigar size alone wouldn’t earn a rightful spot in this list. In order to be considered for our Best Small Cigars for Winter selection, each cigar had to fit the following criteria:
- Provide between 30-60 minutes of smoke time
- Deliver exceptional value
- Offer a variety of pairing choices for winter beverages
- Be something that we would smoke year-round
This list is for all of you that have to double up on your socks and double down on your whiskey in winter months!
Best Small Cigars #7: Illusione Rothchildes CT

Illusione is known for blending very complex, satisfying cigars. But Dion Giolito isn’t only friendly to your palate; he also creates very affordable cigars for the consciences smoker. This makes Illusione an obvious choice for winter smoking even if we didn’t select one of their small cigars.
Most cigar enthusiasts are familiar with the original Rothchildes, but have you ever wondered what would happen if you swapped the Mexican San Andres wrapper with Ecuadorian Connecticut? Turns out, it’s as delightful as it sounds!
We believe Dion said it best in the original release of the Illusione Rothchildes: “New yet familiar, our new release will please the palate and the pocketbook. A stand alone cigar. A stand alone size. A stand alone brand.”
Best Small Cigars #6: Caldwell Long Live the King Harem

When most people think of Caldwell Cigars, they immediately recall unique flavor profiles and exquisite artwork. Love it or hate it, you’ll never smoke a Caldwell cigar and compare it to something else.
In 2016, we fell in love with small cigars and challenged Robert Caldwell to blend us a unique size of Long Live the King. Something we could smoke easily between shipments that wouldn’t commit us to a chair for long periods of time.
Enter the Long Live the King Harem, a Small Batch exclusive run of 4,050 cigars. We’re excited to share this with you, and hope that you enjoy it as much as we do!
Best Small Cigars #5: Crowned Heads La Imperiosa Minutos

In 2014, Crowned Heads created a limited edition line of cigars called Las Calaveras. It was understood at the time that each year would bring a new Las Calaveras, but the 2014 was so well received that the public demanded more.
La Imperiosa was introduced to fill that demand, utilizing the same macro ingredients as Las Calaveras 2014 but offered in different vitolas. The Minutos size quickly became a favorite, as it packs extreme amounts of flavor into such a small cigar!
Best Small Cigars #4: Quesada 40th Anniversary Petite Belicoso

Along with the Long Live the King Harem, we also introduced the Quesada 40th in a Small Batch exclusive size last year. Beginning with Manolo Quesada’s flagship blend, the 40th anniversary, we challenged him to create something with just as much character in a smaller package.
This petite belicoso has everything you could want in a cigar: perfect construction, in your face flavors, and is just the right size for a quick smoke. And, while you may be tempted to pair it with coffee based on the wrapper color, these small cigars are firecrackers!
Best Small Cigars #3: Dunbarton Mi Querida Gordita

If you want a full throttled kick in your small cigars, Mi Querida has you covered! Mi Querida Gordita is a 4 x 48 cigar that was only recently added to the full lineup from Dunbarton Tobacco & Trust. Until now, it was on the secret menu of sorts where select retailers could opt-in if they knew what to ask for.
But the Gordita size isn’t just another addition to the team, it’s a fantastic blend! Starting with the Sobremesa Short Churchill, then the Mi Querida Gordita, and finally the Todos Las Dias Half Churchill, Steve has shown his exceptional skill at blending flavorful, balanced, and complex smaller cigars.
Mi Querida Gordita has recently become a favorite around the shop, and we knew that it would make for an excellent addition to anyone’s winter rotation.
Best Small Cigars #2: Padron 1926 #35 Natural

Ahhhhh Padron. There’s a reason that Padron makes nearly every Best X list in the cigar industry: they produce some of worlds most consistent flavor bombs! And that’s often the best thing that you can ask for in your 30-60 minutes of relaxation in the winter months.
The 1926 Series takes full-bodied to the next level, delivering all of the concentrated flavors that you’d expect but with a luxurious twist. All of the tobaccos used in the 1926 line have been aged for at least five years, giving the #35 an air of refinement that’s hard to come by in such small cigars.
Best Small Cigars #1: Davidoff 702 Entreacto

Over the last few years, Davidoff has challenged public perception by producing bolder cigars than ever before. Bold as in pioneering innovative new tobaccos, bold as in full-bodied cigars, and bold as in revitalizing an iconic brand.
The 702 series utilizes their infamous 702 Wrapper and drapes it over some of the old classics like the Davidoff Entreacto. But what emerges from this marriage isn’t a new face on an old blend, it’s something uniquely bold that’s perfectly suited for those times when you want to smoke the best cigar for your money in the shortest amount of time.
Buy Our Best Small Cigars for Winter Sampler
What are you looking forward to smoking this winter season? Drop a comment below and add to the conversation!
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