Top 5 Churchill Sized Cigars

March 6, 2019

Top 5 Churchill Cigars of 2021

With the weather slowly but surely getting nicer by the day, the chances to enjoy a longer smoke outside are looking bright. A few years back. Nick shared his Top 5 Churchill-sized cigars (that you can check out below) and that list was top-notch. But since then, we’ve had some delicious cigars come out that feature premium, Churchill sizes within their line.

We all know Davidoff reigns supreme with their Churchill smokes, but we have some tasty treats for you from H. Upmann and Foundation that you’ll just love. So if you’re looking to start venturing off into smoking larger cigars, or have been a Churchill aficionado for quite some time, then this list is the one for you.

Here are our Top 5 Churchill-sized cigars in 2021. Don’t forget to check out the limited-time sampler in the link below.

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Davidoff Winston Churchill

Winston Churchill cigars were created to honor the legendary British himself, Mr. Winston Churchill. Churchill was the prime minister of the United Kingdom from 1940-1945, then again from 1951-1955.

Now Winston Churchill was a lover of all cigars, but it is to be rumored that he fell in love with the “Churchill” size after he visited the Romeo y Julieta factory in the late 1940s. Regardless of when it was created, it is all thanks to him that we have a Churchill size at all!

The length of this delicious Churchill is 6.87 while sporting a 47-ring gauge. Cloaked in an Ecuadorian Habano wrapper, with a binder from Mexico and filler tobaccos from Nicaragua, the Davidoff Winston Churchill is a medium-bodied smoke with a plethora of invigorating flavor notes. Your palate will detect almond, wood, sweet cream, and caramel tones throughout the smoke.

If you’re a cigar smoker who’s never experienced a Churchill-sized cigar before, then starting off with the brand that idolizes the man who made these specific sizes popular would be a great start!

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H. Upmann 175th Anniversary

Next up on the list is one of our favorites here at JR, the H. Upmann 175th Anniversary. Altadis created the 175th anniversary with go-to collaborator AJ Fernandez to celebrate H. Upmann’s success in the business since 1844. In order to create a milestone blend for one of the oldest companies in the cigar business, they knew they needed AJ’s magical touch to create this perfect smoke.

Only sold in the Churchill size on our website, the 175th Anniversary by H. Upmann is a 7 x 50 Nicaraguan puro that is a medium to full-bodied gem! With the wrapper being as oily and silky as possible, The H. Upmann 175th is an exceptionally smooth experience from start to finish. The flavor notes you’ll taste throughout are leather, pepper, cashews, and vanilla, which would pair with a nice scotch.

The fitting tribute AJ Fernandez created to celebrate H. Upmann’s 175 years in the cigar industry deserves a spot in your humidor today. Order your box of the H. Upmann 175th Anniversary today before they’re gone for good!

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Illusione Original Documents

This boutique-style smoke made in 2007 was one of the cigars under the Illusione brand that took the industry by storm. Illusione Original Documents were made in small batch quantities under the careful supervision of master blender Dion Giolito. Garnering a cult following right off the bat, the Illusione Original Documents is available in ten different sizes for all to enjoy. However, the one that has our attention is the 42G Slam Double Corona Churchill.

The 42G Slam Double Corona is a Nicaraguan puro that is 7.5 in length and has a size 50 ring gauge. This medium to full-bodied smoke has delicious flavor notes of leather, black cherry, earth, and dried fruit. All of these delicious flavor notes come from being blended with the finest Nicaraguan tobacco Dion provides. This complex, yet satisfying smoke has all the right ingredients for you to enjoy. If you’re a novice smoker, then I’d say the Illusione Original Documents in the Churchill size is the one for you.

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Undercrown cigars came to fruition and made a huge splash after the huge success of Liga Privada. Created by the rollers of Drew Estate factory, the Undercrown uses similar tobaccos used in the Liga Privada #9 but now is more readily available for all to enjoy. Although the Undercrown is available in a number of different shapes and sizes, the Undercrown Churchill is one of our favorite delicious cigars in the Churchill size.

Available in a 7 x 48 size, the Undercrown Churchill is cloaked in a San Andres Negro wrapper, with a Connecticut Habano binder, and filler tobaccos from Brazil and Nicaragua. This medium to full-bodied smoke unveils delicious flavor notes with each and every puff. Notes you’ll detect while smoking the Undercrown Churchill are coffee, dark chocolate, and black pepper. Churchill lovers are in for a real treat due to the glorious taste and aroma of the ever so popular Undercrown Churchill that hails from the great minds over at Drew Estate Cigars.

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Foundation Highclere Castle Victorian

If you ever heard Nick Melillo, founder of Foundation cigars speaks, you know he absolutely loves to add historical themes to all of his cigars. When it comes to the Foundation Highclere Castel Victorian, this line harkens back to the very first cigar that was imported from Cuban to England in the Victorian era. Following the wildly popular Highclere Castle line, the Highclere Castel Victorian in the Churchill size is the last cigar to round out our favorite Churchill cigars of 2021.

Cloaked in an Ecuadorian Habano wrapper, with a binder and wrapper from Nicaragua, the Highclere Castel Victorian is a 7 x 48, medium to full-bodied smoke. The fully aged tobaccos from Esteli and Jalapa Valley boast the flavors in this delicious smoke. Flavor notes you’ll detect while smoking the Highclere Castle Victorian are chocolate, pepper, leather, and oak. For me, this is one smoke that I’m willing to spend hours outside smoking and enjoying each and every puff.

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Top 5 Churchill Cigars of 2019

Here are Nick’s Top 5 Churchill Sized Cigars. Nick explores 5 different Churchills that will last a long time for a relaxing smoke. If you like Nick’s choices, then go check them out today at




Romeo 505 Nicaragua by Romeo y Julieta



Oliva Master Blends 3



Southern Draw 300 Hands



Alec Bradley Prensado



My Father Le Bijou 1922




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