Still Has the Muscle: When Boldness Finds Balance

There are evenings when only a full-bodied cigar will do. With plenty of time to relax on the porch, I reached for the lone CAO Flathead V660 remaining in my humidor. After two years of rest, I was curious whether the big Broadleaf-wrapped cigar had mellowed or if it still possessed the muscle that made it memorable.

With its Connecticut Broadleaf wrapper, Ecuadorian Connecticut binder, and Nicaraguan fillers, the cigar delivers rich notes of semi-sweet chocolate and espresso. Sweet molasses and vanilla undertones balance out the dense, darker flavors, and a bit of pepper adds further interest.

The box-pressed 6 x 60 stick is heavy in the hand, and the red and silver American muscle car-themed banding over the dark chocolate-hued wrapper adds to the imposing presence. Although 60-ring-gauge cigars look impressive, they are not comfortable to hold and smoke in my opinion. However, the box-pressed shape narrows one dimension enough to make it feel noticeably less cumbersome in the hand and between the teeth.

Knowing the Flathead’s reputation for bold flavors, I wanted a bourbon with enough proof and richness to avoid being overshadowed. Elijah Craig Barrel Proof seemed the obvious choice.

This bottle is Batch A124, the first of the three releases for 2024. Bottled at 119 proof and aged 10 years, 9 months, it is one of the lower-proof and younger releases in the series, making it especially approachable. The proof is high enough to add interest but never becomes overwhelming. I’ve greatly enjoyed this bottle and will surely miss it once it’s empty.

This bourbon treats the palate with a robust profile of brown sugar, dark caramel, vanilla, and charred oak, along with a moderate cinnamon-laced finish. Vanilla and a hint of tobacco linger in the finish, which is sweet without becoming syrupy, and there’s just enough rye spice to provide a lively finish.

The Flathead’s black pepper and espresso notes dominated the pairing initially. As I slowly sipped the Elijah Craig Barrel Proof, its caramel and brown sugar notes began to balance and soften the cigar’s pepper. Soon, I found myself thinking of richly caramelized crème brûlée.

As the smoke moved into its second half, the cigar's darker espresso and cocoa notes came into the forefront. The crème brûlée impression gave way to chocolate-covered espresso beans as the culinary imagery continued to fill my thoughts.

The CAO Flathead V660 and Elijah Craig Barrel Proof proved to be a balanced and thoroughly satisfying pairing. Even after two years in the humidor, the Flathead had lost none of the muscle that first made it memorable, standing up easily to the bourbon’s richness and proof. In turn, the bourbon’s sweetness tempered the cigar’s pepper, allowing notes of dark chocolate, espresso, cinnamon, and crème brûlée to shine.

Cheers!

A Porch Pairing for a Summer Afternoon

Here’s a summertime pairing that I tried on a whim, and it turned out even better than expected. Samuel Adams Summer Ale is a seasonal release from the Boston brewery that has been a staple of summer cookouts since 1995. The refreshing 5.3% ABV ale features Hallertau Mittelfrüh noble hops, lemon, lime, and orange peels, along with Grains of Paradise. The result is a crisp beer with a light herbal hop character, bright citrus notes, subtle wheat sweetness, and a gentle peppery spice in the finish.

Summer Ale seemed the perfect choice for a warm, rainy afternoon on the screened porch. Wanting a cigar that wouldn’t overpower the beer, yet still offered a satisfying depth of flavor, I reached for a Rocky Patel A.L.R. (Aged, Limited, and Rare) Second Edition in the Robusto vitola.

The A.L.R. Second Edition is a cigar I’ve enjoyed frequently over the years, resulting in numerous mentions here in these Musings. Wrapped in Mexican San Andrés leaf over a Honduran binder and fillers from Honduras and Nicaragua, the medium-bodied smoke delivers satisfying richness while remaining remarkably balanced. Rocky Patel ages the cigars for two years after rolling, and this particular example had spent an additional 22 months resting in my humidor.

The cigar kicks off with notes of espresso and cocoa. As expected from the San Andrés wrapper, a sweet earthiness balances those darker flavors. Rather than dominating the palate, the wrapper’s natural sweetness softens the bitterness of the espresso and cocoa, creating a rich yet approachable combination.

Medium-bodied rather than powerhouse in strength, the A.L.R. Second Edition emphasizes balance over intensity, making it an ideal companion for Samuel Adams Summer Ale. The beer’s bright citrus, wheat, and subtle spice refresh the palate between draws, lifting the cigar’s espresso, chocolate, and earthy sweetness while providing a crisp contrast to its darker flavors.

Pairing cigars and beer isn’t always about matching intensity. Sometimes the better approach is finding complementary flavors that allow each to shine. In this case, the citrus brightness of the Summer Ale and the earthy sweetness of the San Andrés-wrapped A.L.R. Second Edition came together in a way that was both balanced and thoroughly enjoyable.

Cheers!

An After-Dinner Pairing: Angel’s Envy & Perdomo Reserve Maduro

The run of pleasant weather offered another opportunity for an after-dinner smoke and sip on the screened porch. I reached into the humidor for an aged Perdomo Reserve 10th Anniversary Maduro Epicure, one remaining from a purchase about two and a half years ago. After that extended rest, I expected the cigar’s flavors to have melded beautifully.

The Epicure vitola is a 6 × 54 box-pressed cigar featuring a six-year-old Cuban-seed Nicaraguan Maduro wrapper that spent an additional 14 months aging in bourbon barrels. The binder and filler are also said to be 6-year-aged Cuban-seed Nicaraguan tobaccos. Remembering the espresso and nutty sweetness I’d enjoyed from this cigar in the past, I searched for a bourbon with a similarly dessert-like profile.

I selected an old favorite, Angel's Envy Bourbon Port Wine Barrel Finish. One of the first examples of secondary barrel finishing in American whiskey, Angel's Envy helped popularize the concept. The bourbon undergoes a standard four to six years of aging in new charred oak before spending an additional six months in Portuguese ruby port wine barrels. Although bottled at a modest 86.6 proof, the added layer of dark-fruit richness never obscures the bourbon’s familiar caramel, vanilla, and oak character.

The bourbon barrel aging of the wrapper leaf for the Perdomo Reserve 10th Anniversary Maduro adds a layer of sweetness, softening the darker notes typical of the Maduro wrapper. That added sweetness, combined with the dark fruit and vanilla of the whiskey, created an indulgent pairing for this evening's repast.

The Perdomo cigar kicks off with espresso and cocoa notes. Alongside Angel’s Envy’s vanilla and caramel sweetness, the pairing felt decadent from the first draw. As the cigar developed, the molasses and dark chocolate notes became more pronounced. The bourbon’s candied fruit gently softens the cigar’s peppery edge. As the pairing continues and the fruit, chocolate, and coffee notes intertwine, my thoughts drifted to crème brûlée and tiramisu.

The cigar picks up more of a roasted character toward the finish. Rich tobacco and dark chocolate move to the forefront. The rich fruit sweetness from the Angel’s Envy lingers alongside those flavors, bringing to mind dark chocolate-covered coffee beans and cherries.

Secondary barrel finishing has become increasingly popular in recent years, helped in no small part by the growing number of “cigar blend” whiskies. Whether bourbon- or Scotch-based, I can rarely resist these releases when I spot them on store shelves. As I savored this after-dinner pairing this evening, it struck me that Angel’s Envy is particularly well suited to cigar pairing, even though it wasn’t conceived or marketed with that purpose in mind.

“Dessert-like” may be an overused description in bourbon, cigar, beer, and cocktail reviews — even here in these Musings. In the case of Angel’s Envy Bourbon Port Wine Barrel Finish paired with the Perdomo Reserve 10th Anniversary Maduro, however, the description seems entirely appropriate.

Cheers!

The Overnighter: A Bold Cocktail and Cigar Pairing

The Overnighter cocktail is a four-ingredient drink that’s right up my alley as a fan of bitter and sweet combinations. It’s a flavorful, well-balanced cocktail that’s every bit as enjoyable as it is easy to make.

The Overnighter

• 1.5 oz Rye Whiskey
• .75 oz 22.5 ml Campari
• 1 oz Dry Vermouth
• .25 oz Bénédictine
• Orange wheel for garnish

Combine the liquid ingredients in a mixing glass with ice and stir until well chilled. Strain over a large ice cube into a rocks glass and garnish with the orange wheel. Some recipes call for a smoked orange wheel, which would undoubtedly add another layer of complexity.

I used 90-proof Sazerac Rye for my drink. The Overnighter is moderately strong and meant to be sipped slowly, allowing its contrasting bitter and sweet notes to unfold with each taste.

I’ve seen some versions of the recipe call for ¾ ounce of Bénédictine. I tried one using ½ ounce and found the resulting drink a bit too sweet for my taste. The quarter-ounce measure keeps the herbal liqueur in balance, adding depth without overwhelming the other ingredients.

A bold cocktail like the Overnighter calls for an equally bold, well-balanced cigar. I reached for the El Pulpo by Artesano del Tobacco, a cigar I’ve enjoyed often and was one of my favorite cigars of 2025.

The cigar’s rich notes of dark chocolate, black coffee, and roasted nuts paired beautifully with the Overnighter. It had been a while since I’d smoked an El Pulpo, despite still having an unopened box resting in the humidor. This smoke served as a welcome reminder to crack open that box in the near future.

Cheers!

Toasted Oak, a Cigar, and a Summer Evening

Not long ago, a friend recommended Elijah Craig Toasted Barrel Bourbon to me. Knowing we share a similar appreciation for well-crafted bourbons, it seemed like a recommendation worth following. During a recent it out of state road trip, I made a quick shopping stop and spotted a bottle on the shelf. Even though it’s readily available at home, I picked it up while the recommendation was still fresh in my mind.

I cracked open the bottle one evening last week and enjoyed a pour while relaxing indoors. After an evening with the bourbon on its own, the question became which cigar would best complement its rich toasted sweetness.

We’ve enjoyed a brief respite from the summer heat over the past few days, making time on the porch with a cigar and bourbon especially enjoyable. It also provided the perfect opportunity to pair the Elijah Craig with an E.P. Carrillo Pledge Purple.

Elijah Craig Toasted Barrel Bourbon uses the same mash bill as several of Heaven Hill’s other bourbons. The change occurs in the finishing process. After the usual maturation process, the bourbon spends additional time in a second, custom-toasted new oak barrel. The lighter toast is said to emphasize sweeter, dessert-like flavors rather than the deeper oak influence associated with a heavier char. The bourbon is bottled at 94 proof.

The aroma from the glass is quite rich, with delightful notes of caramel, vanilla, oak, and even some chocolate. The first sip brings baking spices. They soon give way to toffee and caramel, along with lightly toasted wood. The finish lingers with cocoa, oak, and a pleasing hint of smokiness. From the start, I was thinking not only of suitable companion cigars, but also that the toasted bourbon would make a great Old Fashioned.

The E.P. Carrillo Pledge Purple has been sitting in the humidor since I purchased a box in March. The Purple was created to commemorate the fifth anniversary of the highly regarded Pledge line. It uses the same Havana-seed Connecticut wrapper from that original crop which has now been aged an additional five years. Beneath that well-aged wrapper lies a Mexican binder and Nicaraguan fillers from Estelí, Condega, and Ometepe. The Toro vitola is sharply boxed and measures 6 x 54. 

The Pledge Purple profile is complex yet refined and balanced. Throughout the smoke, a blend of cedar, roasted nuts, espresso, cocoa, and mild spice treat the taste buds. The overall impression is creamy and earthy, with a mild natural sweetness to balance the bitter notes.

Enjoyed together, the caramel and toasted notes of the bourbon seemed to accentuate the natural sweetness of the cigar’s aged wrapper. Each leaves a lingering finish that complements the other. Though the bourbon and cigar offered contrasting flavor profiles, they remained remarkably balanced. Neither dominated the pairing, allowing each to complement the other while retaining its own distinct character.

Throughout the 90-minute smoke, I also delighted in the welcome weather. A July evening with temperatures below 80° and humidity under 50 percent provided the perfect backdrop for the pairing. It proved to be one of those evenings where neither the cigar nor the bourbon demanded center stage. Instead, each quietly elevated the other, making for an exceptionally relaxing summer evening.

Cheers!

A Pairing Rooted in Tradition

Perhaps I’ve been feeling nostalgic about our visits to Italy, or perhaps the warm summer evenings have simply had me reaching for lighter, shorter cigar and beverage pairings. Whatever the reason, I’ve been enjoying sipping various amari and other digestif-style beverages after dinner. On one recent evening, I reached for a bottle of Amaro Nonino Quintessentia. Fittingly, I paired it with a Toscano Antico.

Amaro Nonino is an Italian herbal liqueur built on a base of grappa, the grape-pomace spirit for which the Nonino family is renowned. The grappa is infused with a wide assortment of herbs, flowers, bark, and roots before being refined with aged Nonino grape distillate.

The amaro offers a pleasing balance of sweetness and bitterness, with the sweeter notes holding a slight edge. Orange peel, honey, alpine herbs, and a gently bitter marmalade note lead the profile. Though most often served as a digestif, Amaro Nonino is also consumed as an aperitif, most often in a cocktail such as the Amaro Nonino Spritz or a Paper Plane.

Whenever we visit Italy, one of my first stops is a tabaccheria to pick up a few Toscano cigars. Inevitably, a handful make the trip home with me. The Toscano Antico featured here has been resting in my humidor since our Fall 2024 visit.

Toscano Antico is one of the bolder smokes in the Toscano lineup. The wrapper is made from select North American Kentucky, fire-cured for over 30 days using hickory and oak. The binder leaves are a blend of Italian Kentucky, primarily from Tuscany, and North American Kentucky grown in Kentucky and Tennessee. The North American wrapper and extended aging produce a more assertive smoke than classics such as the Toscano Classico.

A Toscano Antico enjoyed alongside Amaro Nonino Quintessentia makes for more than a harmonious pairing. It feels rooted in tradition. Sipping an Italian amaro while smoking Italy’s iconic fire-cured cigar evokes a shared heritage that extends well beyond flavor.

Neither is particularly sweet, nor aggressively bitter. Instead, each occupies the broad middle ground where wood, herbs, spice, and restrained sweetness overlap. Together, they create a pairing that feels unmistakably Italian.

The Toscano Antico opens with the unmistakable aroma of fire-cured Kentucky tobacco. Campfire smoke, toasted oak, black pepper, and dry earth establish a rustic foundation that is bold without becoming harsh. As the cigar settles, notes of leather, roasted walnuts, bitter cocoa, and espresso emerge, adding depth while retaining its characteristically savory profile.

The initial flavors of this particular cigar were softer than I remember from freshly purchased examples. That gentle rounding of the profile is exactly what I expected after two years of rest, as the flavors have had time to meld and mellow.

The first sip of the Amaro Nonino introduced orange peel, honey, alpine herbs, and warm baking spices to the mix. The honey lends just enough sweetness to soften the sharper edges of the Kentucky tobacco.

One of the more surprising aspects of the pairing is how it changes both components. The cigar becomes slightly rounder and more refined, while the amaro loses much of its perceived sweetness, revealing additional layers of herbs and spice. 

As with my earlier pairing of Southern Draw Evening Primrose and Amaro Montenegro, I found that those moments are what make pairing cigars with amari so enjoyable. Neither simply accompanies the other; rather, each subtly reshapes the experience of the other. Discovering those changes is part of the pleasure.

Midway through the smoke, the cigar truly hits its stride. Deeper cocoa and espresso notes emerge. The interplay of bitter cocoa and espresso from the cigar complements the orange marmalade, toasted oak, vanilla, and herbal complexity of the amaro. Even in the finish, the flavors linger on the palate with lasting wood smoke, herbs, citrus, and sweet nuts.

As the cigar neared its end, nearly ninety minutes after lighting, roasted wood and black pepper reached their peak. The warm herbs and bright citrus of the Nonino refreshed the palate, keeping the final third from becoming heavy.  

I found myself slowing down, allowing several minutes between draws and small sips. The Toscano Antico burned slowly and steadily, requiring little attention beyond simply savoring the flavors.

Toscano Antico and Amaro Nonino proved to be an exceptionally satisfying after-dinner combination. More than simply complementing one another, they captured something of the relaxed rhythm of evenings we’ve enjoyed in Italy.

As the sun slowly disappeared beyond the trees, I found myself thinking once again of the sunsets over the canals of Venice. While I may have been sitting on a screened porch in rural Virginia rather than beside an Italian canal, for an hour and a half, the pairing brought those memories pleasantly back to life.

Cheers!

Summer Skies, a Bourbon Spritz, and a Fine Cigar

For our Sunday afternoon aperitivo, Colleen’s usual warm-weather choice is an Aperol Spritz. I’ll often join her in that selection, but this time I was looking for something a bit bolder while still retaining the refreshing character of the classic. Enter the Bourbon Aperol Spritz.

I already had the ingredients assembled for the Aperol Spritz, so all I needed to do was reach for the bourbon and adjust the proportions slightly.

Bourbon Aperol Spritz

• 1½ oz bourbon
• 1 oz Aperol
• 2 oz Prosecco
• 1 oz club soda
• Orange slice

Build the drink over ice, stir gently, and garnish with an orange slice.

The very first sip struck me as slightly out of balance, but the flavors quickly came together, perhaps helped by the slight dilution from the melting ice. With each sip, the drink became more harmonious and increasingly refreshing.

The finished cocktail is lighter and brighter than an Old Fashioned or even a Boulevardier, making it especially enjoyable during the summer months. The bourbon contributes notes of vanilla, caramel, and oak that are balanced nicely by Aperol’s bittersweet orange character and the effervescence of the Prosecco and club soda.

Naturally, I needed a cigar to accompany the spritz. Turning to the humidor, I selected an Oliva Serie V Melanio in the Robusto vitola.

This cigar was the last remaining from a box purchase and had rested loose in the humidor for more than two years. It showed a bit of damage to the foot and cap but was otherwise in excellent condition and performed flawlessly.

The Serie V Melanio proved an excellent companion to the cocktail. Its notes of cedar, cream, toasted nuts, and baking spices complemented the bourbon beautifully while allowing Aperol’s bittersweet orange character to remain prominent. The cigar’s creamy texture also paired especially well with the bourbon’s sweet vanilla and caramel notes.

As we sat and enjoyed our aperitivo, the skies alternated between bright sunshine and dark summer clouds, tempering the July heat. A brief shower finally arrived — lasting only a few minutes — but it cooled the air just enough to make the afternoon even more enjoyable. The Bourbon Spritz, the Oliva Serie V Melanio, and, of course, the light snacks alongside them all combined to make for a thoroughly pleasant afternoon on the porch.

Cheers!

A Sweltering Evening with Southern Draw and Montenegro

The news and social media are full of reports about the extreme heat affecting much of the country, Virginia included. For my part, I accept that it’s July in Virginia. Temperatures approaching 100° are neither unusual nor unexpected. However, with “feels like” temperatures nearing 110° predicted over the next couple of days, I decided to get an early start on watering the lawn while enjoying a cigar on the screened porch, when the actual temperature was only 92°.

I searched for a light, refreshing digestif and settled on Amaro Montenegro. I’ve been slowly acquiring an assortment of amari. These Italian herbal liqueurs are crafted from a variety of botanicals infused or macerated in alcohol. Although bitterness lies at their core, they offer a wide spectrum of flavors ranging from sweet citrus and floral notes to warming spices and earthy herbs. They are typically served neat as a digestif, though many also shine in cocktails.

Amaro Montenegro is one of the gentlest and most approachable of the amari. With a restrained bitterness, it offers notes of candied orange peel, vanilla, and honey. The floral sweetness balances bitterness without being cloying or syrupy. 

I selected a Southern Draw Evening Primrose for the cigar accompaniment. I've had some in the 5½ x 54 Robusto size in the humidor since June 2025. The cigar features an Ecuadorian Habano Rosado wrapper, an Indonesian Sumatra binder, and fillers from several growing regions of Nicaragua. Though the cigar features a moderate pepper component, it is balanced by a subtle floral sweetness layered with cedar, toasted nuts, citrus, and delicate floral aromas.

It was that underlying floral sweetness that led me to pair the Evening Primrose with the Amaro Montenegro.

The initial draw delivered a substantial burst of pepper and cedar, which briefly gave me pause about the pairing. Almost immediately, however, those bold flavors were tempered by notes of toasted bread and a creamy floral sweetness. I spent several minutes simply enjoying the cigar’s balanced complexity before reaching for the amaro. The combination of gentle pepper, toasted bread, roasted nuts, soft spices, and sweet citrus was thoroughly enjoyable on its own.

Taking my first sip of the amaro confirmed that I had made the right choice. Despite their contrasting flavor profiles, the pairing was remarkably complementary. Montenegro’s orange and honey notes softened the cigar’s early pepper, making the smoke seem creamier. As the cigar developed richer cedar and toasted nut flavors, the amaro contributed hints of vanilla and baking spice that seemed to emerge naturally from the cigar rather than stand apart from it.

The floral interplay between the two was particularly striking. The Evening Primrose’s subtle floral nuances were gently elevated by Montenegro’s delicate botanicals, bringing those notes to the forefront and lending the cigar even greater elegance.

As the hour-long smoke drew to a close, the cigar developed deeper roasted flavors. Amaro Montenegro’s restrained bitterness and honeyed sweetness refreshed the palate between puffs, allowing the cigar’s complexity to continue unfolding. Rather than overwhelming the cigar, the amaro accentuated its more delicate flavors, creating a balanced and sophisticated after-dinner pairing.

Despite the oppressive heat and humidity that pushed the “feels like” temperature close to 100°, the complementary flavors of the Southern Draw Evening Primrose and Amaro Montenegro provided a refreshing counterpoint to the evening. As I settled into the pairing, time passed quickly, and the summer heat seemed almost an afterthought.

Cheers!