The Chief’s Picks include hand-selected recommendations and favourites by Cigar Chief. Not sure what you’re shopping for? The Chief’s Picks are always a great choice whether you’re looking for something new or trying an old favourite again.

Shop All Chief's Picks

5-5-5 Bundle

Original price was: $328.75.Current price is: $230.12.

AJ Fernandez Enclave Broadleaf Belicoso

Original price was: $21.29.Current price is: $18.10.

AJ Fernandez Enclave Broadleaf Churchill

Original price was: $19.56.Current price is: $16.63.

AJ Fernandez Enclave Churchill

Original price was: $19.56.Current price is: $16.63.

AJ Fernandez Enclave Figurado

Original price was: $20.72.Current price is: $17.61.

AJ Fernandez New World Dorado Gordito

Original price was: $26.40.Current price is: $22.44.

AJ Fernandez New World Dorado Toro

Original price was: $25.23.Current price is: $21.45.

Brick House Corona Larga Double Connecticut

Original price was: $15.70.Current price is: $12.56.

Puff after puff you’ll be met with tame hints of sweet cedar, cream, and toast.

Brick House Mighty Mighty Double Connecticut

Original price was: $15.82.Current price is: $12.66.

Puff after puff you’ll be met with tame hints of sweet cedar, cream, and toast.

Brick House Mighty Mighty Maduro

Original price was: $15.82.Current price is: $12.66.

Brick House Maduro is rolled with the same highly-acclaimed Brick House filler blend and finished with a Brazilian Arapiraca wrapper.

Brick House Robusto

Original price was: $13.13.Current price is: $10.50.

Made with an attractive wrapper and three-seam cap, this robust cigar imparts a soft, cedary smoke to the palate. The finish is very fruity.

Brick House Robusto Maduro

Original price was: $13.13.Current price is: $10.50.

The slow burn stays even and burns well from start to finish. The smoke has notes of cocoa and sweetness with a rich well balanced flavor profile.

CAO Mx2 Robusto

Original price was: $15.38.Current price is: $13.07.

If you like maduro wrappers, then you’ll love CAO Mx2. It has, well, two of them: a well-fermented Connecticut Broadleaf and a spicy Brazilian, which is used as the binder.

Casa Magna Colorado Robusto

Original price was: $17.14.Current price is: $15.43.

A smooth full flavored smoke that offers the smoker rich coffee notes balanced by a cedary sweetness and a hint of raisins.

Cigar Chief Classic Connecticut Robusto by Claudio Sgroi

$6.75

As you light up, you’ll be embraced by a creamy, mild smoke with nuanced flavors of cedar, toasted almonds, and a subtle hint of white pepper.

Cigar Chief x Escobar Habano Robusto

$8.00

Cigar Chief’s 2024 House Blend is made in collaboration with the cigar experts at Escobar Cigars. This newly crafted premium blend is made at the PDR cigar factory in the Dominican Republic with the legendary master blender Abe Flores.

Cigar Chief x Escobar Premium Blend Connecticut Robusto

Original price was: $15.95.Current price is: $11.96.

Cigar Chief’s 2024 House Blend features a premium, 5-year-aged filler crafted in collaboration with Escobar Cigars. Made at the PDR factory in the Dominican Republic by master blender Abe Flores, it boasts a curly head, closed foot, and a high-priming Connecticut wrapper for a rich, balanced experience.

Don Tomas Clasico Rothschild

Original price was: $9.15.Current price is: $7.78.

This is a 100% handmade long-filler premium cigar delivering flavors of coffee, toast, and spice.

Drew Estate Factory Smokes Maduro Robusto

Original price was: $8.55.Current price is: $6.41.

Escobar Ultra Black Platinum Series

Original price was: $28.88.Current price is: $20.22.

Foundation The Upsetters Connecticut Shade Small Axe

Original price was: $14.33.Current price is: $11.46.

Macanudo M Coffee Toro

Original price was: $15.17.Current price is: $11.38.

Oliva Cain 654T Maduro

Original price was: $21.09.Current price is: $16.87.

Oliva Cain 660 Maduro

Original price was: $23.98.Current price is: $19.18.

Oliva Cain Daytona 654T

Original price was: $23.15.Current price is: $18.52.

Oliva Cain Daytona Corona

Original price was: $16.40.Current price is: $13.12.

Oliva Cain Daytona Double Toro

Original price was: $23.15.Current price is: $18.52.

Oliva Cain F 654T

Original price was: $23.98.Current price is: $19.18.

Oliva Cain F 660

Original price was: $25.08.Current price is: $20.06.

Oliva Cain F Robusto

Original price was: $20.26.Current price is: $16.21.

Oliva Cain Habano 660

Original price was: $21.30.Current price is: $17.04.

Oliva Master Blends Churchill

Original price was: $37.87.Current price is: $30.30.

Oliva Master Blends Torpedo

Original price was: $41.01.Current price is: $32.81.

Oliva Serie G Maduro Belicoso

Original price was: $19.16.Current price is: $15.33.

Oliva Serie G Maduro Perfecto

Original price was: $19.22.Current price is: $15.38.

Oliva Serie G Maduro Presidente

Original price was: $19.48.Current price is: $15.58.

Oliva Serie O Robusto

$19.51

Made in the original Cuban tradition of growing the same Habano seed in diverse regions of the country to produce a distinct blend.

Oliva Serie O Toro

$21.00

Made in the original Cuban tradition of growing the same Habano seed in diverse regions of the country to produce a distinct blend.

Oliva Serie V Liga Especial No. 4

$20.53

Five years in the making, this special cigar is sure to exceed a premium cigar smoker’s highest expectations.