The Ultimate Cigar & Whiskey Pairing Guide: 20 Perfect Matches

At Bourbon Blackpool, we believe the finest pleasures in life are best enjoyed together. A great cigar and an exceptional whiskey share more than a moment — they share flavour architecture. Both are shaped by terroir, ageing, fermentation, and the hand of a master craftsman. When the right cigar meets the right dram, the result is something greater than the sum of its parts.

We've curated 20 definitive pairings from our collection — matching our premium cigars with our hand-selected whiskey samples. Whether you're a seasoned aficionado or just beginning your journey, this guide will help you explore the art of pairing with confidence.

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How to Pair Cigars & Whiskey

The golden rule is complement or contrast. A rich, full-bodied cigar can be complemented by a bold, high-proof bourbon — or contrasted beautifully with a delicate, floral Japanese whisky. Consider strength, body, and flavour notes: earthy cigars love peaty Scotch; creamy, milky cigars sing alongside wheated bourbons; spicy, peppery smokes demand a rye.

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The 20 Pairings

1. Montecristo No. 2 × Pappy Van Winkle 20 Year Old

Cigar: Montecristo No. 2 Cuban Cigar
Whiskey: Pappy Van Winkle 20 Year Old | 45.2% Abv | 30ml Sample

Tasting Notes: The Montecristo No. 2 is arguably the world's most celebrated Cuban cigar — a torpedo of extraordinary complexity delivering cedar, dark chocolate, espresso, and a whisper of dried fruit. Pappy Van Winkle 20 Year Old is the holy grail of wheated bourbon: impossibly smooth, with vanilla custard, toffee, dried apricot, and a long, warming finish. Together, they create a luxurious dialogue of sweetness and depth. The cigar's earthy backbone grounds Pappy's ethereal sweetness, while the bourbon amplifies the chocolate and fruit notes in the smoke.

Best enjoyed: After dinner, in a leather armchair, with absolutely nowhere to be.

2. Cohiba Siglo I × Blanton's Straight from the Barrel

Cigar: Cohiba Siglo I Cigar - Tubo
Whiskey: Blanton's Straight from the Barrel | 63.1% Abv | 30ml Sample

Tasting Notes: The Cohiba Siglo I is a short, elegant smoke — grassy, creamy, and lightly spiced with a refined sweetness. Blanton's Straight from the Barrel is a powerhouse: raw honey, charred oak, cinnamon, and a volcanic finish. The contrast here is the magic. The cigar's delicacy tames the bourbon's ferocity, while the bourbon's intensity draws out hidden spice in the Cohiba. A pairing of opposites that works in perfect harmony.

Best enjoyed: As an aperitif pairing before a long evening session.

3. Partagas Serie D No. 5 × Stagg Jr Bourbon

Cigar: Partagas Serie D No. 5 Cuban Cigar
Whiskey: Stagg Jr Bourbon | 64.45% Abv | 30ml Sample

Tasting Notes: Partagas Serie D No. 5 is a powerhouse robusto — full-bodied, earthy, and loaded with leather, dark spice, and cocoa. Stagg Jr is one of the most intense bourbons in the Buffalo Trace stable: barrel-proof, with dark cherry, brown sugar, and a long, fiery finish. This is a pairing for those who like their pleasures bold and unapologetic. The cigar's earthiness cuts through the bourbon's sweetness, creating a beautifully balanced, full-throttle experience.

Best enjoyed: On a cold evening with a single large ice cube in the glass.

4. Romeo y Julieta Churchill × Buffalo Trace Single Barrel Select

Cigar: Romeo y Julieta Churchill Long Cigar - Tubo
Whiskey: Buffalo Trace Single Barrel Select - 003 - Bourbon Blackpool | 700ml

Tasting Notes: This is our house pairing — and it's personal. The Romeo y Julieta Churchill is a long, elegant smoke with cedar, floral notes, and a creamy, medium-bodied profile. Our own Buffalo Trace Single Barrel Select — rated 94.75/100 in Jim Murray's Whisky Bible 2025–2026 — delivers caramel, vanilla, toasted oak, and a beautifully clean finish. The cigar's floral elegance lifts the bourbon's sweetness, while the bourbon's oak character adds depth to the smoke. A pairing we're genuinely proud of.

Best enjoyed: Celebrating something worth celebrating.

5. Cohiba Maduro 5 Secretos × Woodford Reserve Double Oaked

Cigar: Cohiba Maduro 5 Secretos Cigar
Whiskey: Woodford Reserve Double Oaked | 43.2% Abv | 30ml Sample

Tasting Notes: The Cohiba Maduro 5 Secretos is one of Cuba's most complex cigars — aged five years in maduro wrapper, it delivers dark chocolate, espresso, dried plum, and a silky, almost sweet finish. Woodford Reserve Double Oaked is finished in a second deeply toasted barrel, producing rich caramel, dark fruit, and a velvety mouthfeel. This is a pairing built on shared DNA: both are dark, rich, and deeply satisfying. The chocolate in the cigar and the caramel in the bourbon create a dessert-like experience.

Best enjoyed: As a post-dinner indulgence in place of dessert.

6. H. Upmann Magnum 50 × Elijah Craig Single Barrel 18 Year Old

Cigar: H. Upmann Magnum 50 Cuban Cigar
Whiskey: Elijah Craig Single Barrel 18 Year Old | 45% Abv | 30ml Sample

Tasting Notes: H. Upmann Magnum 50 is a refined, medium-to-full-bodied Cuban with notes of cream, nuts, cedar, and a gentle spice. Elijah Craig 18 Year Old is a masterclass in aged bourbon — dried fruit, dark toffee, leather, and a long, warming finish. The cigar's creaminess softens the bourbon's oak-forward intensity, while the bourbon's dried fruit notes echo the cigar's natural sweetness. An elegant, unhurried pairing for a long afternoon.

Best enjoyed: On a Sunday afternoon with no agenda.

7. Montecristo Edmundo × Orphan Barrel Rhetoric 25 Year

Cigar: Montecristo Edmundo Cuban Cigar
Whiskey: Orphan Barrel Rhetoric 25 Year | 45.5% Abv | 30ml Sample

Tasting Notes: The Montecristo Edmundo is a wide-ring Cuban with a rich, full-bodied profile — cedar, leather, dark cocoa, and a long, complex finish. Orphan Barrel Rhetoric 25 Year is a rare, deeply aged bourbon with dried fruit, tobacco leaf, dark chocolate, and a remarkably smooth finish for its age. The tobacco notes in the bourbon mirror the cigar's character in a rare moment of true synergy. This is a pairing for the serious aficionado.

Best enjoyed: Slowly. Very slowly.

8. Trinidad Reyes × Weller Special Reserve

Cigar: Trinidad Reyes Cigar
Whiskey: Weller Special Reserve Bourbon | 45% Abv | 30ml Sample

Tasting Notes: Trinidad Reyes is a small, refined Cuban — light-to-medium bodied with delicate floral notes, cedar, and a creamy, slightly sweet finish. Weller Special Reserve is the entry point to the wheated Weller family: soft, approachable, with honey, vanilla, and a gentle warmth. This is a pairing of understated elegance. Neither overpowers the other — they simply make each other better. Perfect for those new to pairing, or those who appreciate subtlety.

Best enjoyed: As an introduction to the world of cigar and whiskey pairing.

9. Hoyo de Monterrey Epicure No. 2 × Makers Mark Cellar Aged 2024

Cigar: Hoyo de Monterrey Epicure No. 2 Tubo Cuban Cigar
Whiskey: Makers Mark Cellar Aged 2024 Release | 59.7% Abv | 30ml Sample

Tasting Notes: Hoyo de Monterrey Epicure No. 2 is one of Cuba's most beloved robustos — medium-bodied, creamy, and wonderfully balanced with notes of hay, cedar, and a gentle sweetness. Maker's Mark Cellar Aged 2024 is a cask-strength expression with amplified fruit, caramel, and a warming spice. The cigar's creaminess is a perfect foil for the bourbon's intensity, and the bourbon's fruit notes bring out a hidden sweetness in the smoke.

Best enjoyed: Mid-afternoon, when the day is at its most relaxed.

10. E.P. Carrillo Allegiance Confidant × WhistlePig 12 Year World Rye

Cigar: E.P. Carrillo Allegiance Confidant Cigar
Whiskey: WhistlePig 12 Year Old World Rye | 63% Abv | 30ml Sample

Tasting Notes: The E.P. Carrillo Allegiance Confidant is an award-winning New World cigar — full-bodied, with dark pepper, leather, and a rich, complex finish. WhistlePig 12 Year World Rye is a bold, high-proof rye with black pepper, dried fruit, and a long, warming finish. This is a pairing of shared spice — the rye's peppery character mirrors the cigar's bold profile, creating a seamless, intensely flavourful experience. Not for the faint-hearted.

Best enjoyed: With a bold playlist and no distractions.

11. My Father The Judge × Garrison Brothers Cowboy Bourbon 2023

Cigar: My Father The Judge Corona Gorda - 98/100 Award Winning Cigar
Whiskey: Garrison Brothers Cowboy Bourbon 2023 | 70.45% Abv | 30ml Sample

Tasting Notes: My Father The Judge is one of the highest-rated cigars ever produced — a Nicaraguan masterpiece with dark chocolate, espresso, black pepper, and a long, complex finish. Garrison Brothers Cowboy Bourbon is Texas bourbon at its most extreme: barrel-proof, with dark fruit, charred oak, vanilla, and a finish that lasts for minutes. Two award-winning heavyweights in one glass and one hand. The cigar's complexity matches the bourbon's intensity note for note.

Best enjoyed: When you want to remind yourself why you started this hobby.

12. Bolivar Petit Coronas × Springbank 15 Year Old

Cigar: Bolivar Petit Coronas Cuban Cigar
Whiskey: Springbank 15 Year Old | 46% Abv | 30ml Sample

Tasting Notes: Bolivar Petit Coronas is a small but mighty Cuban — full-bodied for its size, with leather, dark earth, and a robust, satisfying finish. Springbank 15 Year Old is a Campbeltown Scotch of rare character: sherry-influenced, with dried fruit, toffee, a hint of brine, and a long, complex finish. The cigar's earthiness and the whisky's maritime character create a beautifully rugged pairing — like a walk along a windswept coastline with a good smoke in hand.

Best enjoyed: Outdoors, if the weather permits.

13. Blackbird Crow San Andres × Laphroaig 10 Year Old

Cigar: Blackbird Crow San Andres Corona Cigar
Whiskey: Laphroaig 10 Year Old | 40% Abv | 30ml Sample

Tasting Notes: The Blackbird Crow uses a San Andres Mexican maduro wrapper — dark, oily, and full of dark chocolate, coffee, and earthy sweetness. Laphroaig 10 Year Old is the benchmark peated Islay Scotch: medicinal, smoky, with seaweed, iodine, and a surprisingly sweet finish. This is a pairing of smoke meeting smoke — the cigar's natural earthiness and the whisky's peat create a layered, complex experience that rewards patience. A conversation starter in every sense.

Best enjoyed: With an open mind and a curious palate.

14. Cohiba Panetelas × Hibiki Japanese Harmony

Cigar: Cohiba Panetelas Cuban Cigar
Whiskey: Hibiki Japanese Harmony | 43% Abv | 30ml Sample

Tasting Notes: Cohiba Panetelas is a slender, elegant Cuban — light-to-medium bodied with grassy, floral, and creamy notes. Hibiki Japanese Harmony is a blended Japanese whisky of extraordinary refinement: honey, rose, white peach, and a silky, delicate finish. This is the most elegant pairing on the list — two expressions of precision craftsmanship from opposite ends of the world. The cigar's floral notes and the whisky's fruit create a pairing of rare beauty.

Best enjoyed: In quiet contemplation.

15. Montecristo Wide Edmundo × Nikka Whisky From The Barrel

Cigar: Montecristo Wide Edmundo Cuban Cigar
Whiskey: Nikka Whisky From The Barrel | 51.4% Abv | 30ml Sample

Tasting Notes: The Montecristo Wide Edmundo is a wide-ring Cuban with a rich, full-bodied profile — cedar, leather, dark cocoa, and a long, complex finish. Nikka From The Barrel is Japan's most celebrated cask-strength blend: malt and grain whiskies married to produce a rich, complex dram with dried fruit, vanilla, and a warming, spiced finish. The cigar's cedar and cocoa notes find a natural partner in the whisky's fruit and spice. A pairing that bridges East and West.

Best enjoyed: When you want something familiar yet surprising.

16. Punch 48 Speciality × High West Prisoner Share 2024

Cigar: Punch 48 Speciality Cuban Cigar
Whiskey: High West Prisoner Share 2024 | 51% Abv | 30ml Sample

Tasting Notes: Punch 48 is a medium-to-full-bodied Cuban with a distinctive, slightly rustic character — earthy, woody, and satisfying. High West Prisoner Share is a unique American whiskey finished in wine barrels, delivering dark fruit, vanilla, and a rich, complex sweetness. The wine-cask influence in the bourbon brings out a fruity sweetness in the cigar that you wouldn't otherwise notice. A pairing that surprises and rewards.

Best enjoyed: When you're feeling adventurous.

17. Oliva Serie G Cameroon × Macallan 12 Year Old Sherry Oak

Cigar: Oliva Serie G Cameroon Cigar
Whiskey: The Macallan 12 Year Old Sherry Oak | 40% Abv | 30ml Sample

Tasting Notes: Oliva Serie G Cameroon uses a rare Cameroon wrapper — medium-bodied, with a distinctive sweetness, cedar, and a smooth, creamy finish. The Macallan 12 Sherry Oak is the world's most recognised Scotch: rich sherry, dried fruit, ginger, and a warming, long finish. The Cameroon wrapper's natural sweetness and the Macallan's sherry influence are a match made in heaven — both rich, both sweet, both deeply satisfying.

Best enjoyed: As a gift to yourself after a long week.

18. Diamond Crown Maduro Robusto × Ironroot Harbinger 2024

Cigar: Diamond Crown Maduro Robusto No. 5 Dominican Republic Cigar
Whiskey: Ironroot Harbinger 2024 | World's Best Bourbon Winner | 57.5% Abv | 30ml Sample

Tasting Notes: Diamond Crown Maduro Robusto is a premium Dominican cigar with a dark, oily maduro wrapper — full-bodied, with dark chocolate, espresso, and a long, satisfying finish. Ironroot Harbinger 2024 is the World's Best Bourbon — a Texas expression with dark fruit, caramel, and a rich, complex finish. Two award-winners, one extraordinary pairing. The cigar's dark chocolate notes and the bourbon's caramel create a dessert-like experience of the highest order.

Best enjoyed: When only the best will do.

19. Vegueros Entretiempos × Old Rip Van Winkle 10 Year Old

Cigar: Vegueros Entretiempos Cuban Cigar
Whiskey: Old Rip Van Winkle 10 Year Old | 53.5% Abv | 30ml Sample

Tasting Notes: Vegueros Entretiempos is a medium-bodied Cuban with a light, grassy character — cedar, hay, and a gentle creaminess. Old Rip Van Winkle 10 Year Old is the entry point to the Van Winkle family: wheated, smooth, with honey, vanilla, and a soft, warming finish. This is a pairing of gentle pleasures — neither too bold, neither too subtle. The cigar's lightness allows the bourbon's delicate sweetness to shine, while the bourbon adds warmth and depth to the smoke.

Best enjoyed: On a warm evening as the sun goes down.

20. Cuaba Tradicionales × Johnnie Walker Blue Label

Cigar: Cuaba Tradicionales Cuban Cigar
Whiskey: Johnnie Walker Blue Label | 40% Abv | 30ml Sample

Tasting Notes: Cuaba Tradicionales is one of Cuba's most distinctive cigars — a double figurado (pointed at both ends) with a medium-to-full body, delivering cedar, leather, and a refined, complex finish. Johnnie Walker Blue Label is the pinnacle of blended Scotch: silky, complex, with dried fruit, dark chocolate, smoke, and a finish of extraordinary length. Both are icons of their respective worlds. Together, they represent the very best of what cigar and whiskey culture has to offer — a fitting finale to any evening.

Best enjoyed: As the last pairing of the night, when the conversation has slowed and the evening is at its finest.

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Explore Our Full Range

Every whiskey sample on this list is available as a 30ml tasting pour — the perfect way to explore a new expression before committing to a full bottle. Every cigar is hand-selected by our team for quality, consistency, and value.

Browse our full cigar collection and whiskey samples to build your own pairing experience — or explore our curated gift sets for a ready-made pairing experience.

Bourbon Blackpool — where every smoke tells a story.