The 5 Years of 1 Cigar of the Year sampler is a rare, curated collection celebrating five modern classics — each honored as Cigar of the Year by Cigar Aficionado over a decade of excellence. Spanning multiple countries, blending styles, and eras, this sampler captures what it truly means to reach the pinnacle of premium cigar craftsmanship. Every cigar included didn’t just impress — it stood above thousands of others to earn the industry’s highest recognition.

This collection offers a journey through evolving cigar profiles, from refined elegance to bold, contemporary power. Whether you’re a seasoned aficionado, a collector building a legacy humidor, or a smoker seeking to understand what defines greatness, this sampler delivers five unforgettable experiences — each representing the very best of its year.

Included Cigars & Ratings

The 2011 Alec Bradley Prensado Churchill earned a 96 rating, marking a turning point in modern cigar history. Known for its richness and balance, it delivers layered notes of cocoa, espresso, leather, and spice, wrapped in a dark Honduran leaf that helped redefine what a boutique brand could achieve at the highest level.

The 2015 My Father Le Bijou 1922 Torpedo received a 97 rating, showcasing bold Nicaraguan power with precision. Expect deep flavors of pepper, earth, cocoa, and espresso, delivered with intensity and structure — a cigar that exemplifies strength refined by masterful blending.

The 2018 E.P. Carrillo Encore Majestic captured a 96 rating, celebrated for its elegance and harmony. Crafted entirely from Nicaraguan tobaccos, it offers refined notes of cedar, cream, sweet spice, and toasted nuts, proving that balance can be just as captivating as power.

The 2019 Aging Room Quattro Nicaragua Maestro Torpedo earned a 96 rating, delivering complexity and richness with remarkable smoothness. Layers of cocoa, earth, leather, and spice unfold seamlessly, supported by flawless construction and a long, satisfying finish.

The 2020 E.P. Carrillo Pledge Prequel Robusto earned a standout 98 rating, becoming one of the highest-scoring cigars of its era. Bold, modern, and expressive, it delivers dark chocolate, black pepper, espresso, and leather with exceptional depth and balance — a benchmark for contemporary full-bodied cigars.

Together, these five cigars form a sampler that transcends trends, offering a true education in what defines a Cigar of the Year — balance, complexity, construction, and lasting impression.

Vintage Vinny:
“This sampler is a timeline of greatness. Each cigar captures the soul of its year — you can taste the evolution.”

Toro Tommy:
“Five different styles, five champions. No filler, no fluff — just heavy hitters.”

Boutique Betty:
“If you want to understand why these cigars won, smoke them side by side. It’s eye-opening.”

This sampler isn’t built on hype — it’s built on proof. Each cigar earned its title through blind tasting, rigorous evaluation, and consistent excellence. Together, they showcase how premium cigars have evolved over the years while maintaining the timeless qualities that define greatness.

At CigarsDirect, every cigar in this sampler is sourced directly from authorized distributors and stored in precision-controlled humidors to preserve freshness, aroma, and integrity. Each order is carefully inspected by experienced tobacconists before shipping. We stand behind every purchase with our 100% Money-Back Promise and offer free shipping on orders over $99, ensuring complete confidence from checkout to first light.

All tasting notes and quotes from our “Cigar Sommeliers” are voiced by fictional AI personas created for educational and storytelling purposes. Flavor descriptions reflect general impressions; individual experiences may vary.

FAQs — 5 Years of 1 Cigar of the Year

How long does it take to smoke each cigar in this sampler?
Most cigars take 75 to 120 minutes to smoke, depending on size and smoking pace.

Are these the exact cigars that won Cigar of the Year?
Yes. Each cigar included received a Cigar of the Year designation from Cigar Aficionado.

What strength range should I expect?
This sampler spans medium-full to full-bodied profiles, offering depth, balance, and intensity.

Is this sampler suitable for collectors?
Absolutely. These are landmark cigars that belong in any serious humidor.

Can newer smokers enjoy this sampler?
Best suited for intermediate to experienced smokers due to strength and complexity.

Why choose this sampler instead of individual cigars?
It offers unmatched value, historical significance, and variety in one curated experience.

This Sampler includes 1 of each of the following cigars....

1 - 2011 Alec Bradley Prensado Churchill

1 - 2015 My Father Le Bijou 1922 Torpedo

1 - 2018 E.P. Carrillo Encore Majestic

1 - 2019 Aging Room Quattro Nicaragua Maestro Torpedo

1 - 2020 E.P. Carrillo Pledge Prequel Robusto