Gonzalo Vallejos Cocktail Guide

A practical path to building a small home bar

This is not meant to be a complete cocktail encyclopedia. It is a personal guide to the cocktails I enjoy, the bottles I like, and the way I would build a small home bar gradually.

Most cocktail books are organized in one of two ways: by base spirit, like gin, whiskey, rum, and tequila; or by cocktail archetypes, like sours, old-fashioneds, martinis, and highballs. Some guides also start with the most classic or historically important recipes.

This guide does something different.

It starts with three of my favorite cocktails, then expands from the bottles used to make them. That feels more practical to me because one of the hardest parts of getting into cocktails is not understanding the recipes; it is knowing which bottles to buy first. People get lost quickly when every drink seems to require another liqueur, another spirit, or another modifier.

So the idea here is simple: start with a few drinks I love, buy the bottles for those, and then ask, “What else can we make with what we already have?”

Some bottles in this guide are substitutions for more expensive or harder-to-find ingredients. That is intentional. I would rather start with approachable versions first, and then upgrade later once you know which drinks are worth it for you.

Section 1: The Trio

I want to start this guide with three cocktails that are among my personal favorites:

• Last Word
• Naked & Famous
• Monte Cassino

I often make one of them when hosting friends, and sometimes all three for birthday celebrations. They are not just drinks I enjoy; they are drinks I remember. They feel festive, distinctive, and a little unexpected.

They also share a simple structure: equal parts. That makes them easy to memorize, but still impressive to serve.

The Last Word is the template: a base spirit, an herbal liqueur, a sweet liqueur, and citrus. The other two drinks in this section follow that same idea in different directions, and later drinks — like Oh My Word! and Paper Plane — will build on similar equal-parts logic.

Shopping List

This section starts with approachable bottles. Some of the classic recipes use Chartreuse, but I recommend starting with Genepy first. It will not taste exactly the same, but it gives you a similar herbal direction at a more approachable price.

The point is not to avoid the classic bottles forever. The point is to try the structure first, learn which drinks you love, and then decide where upgrading makes sense.

Recommended starter bottles

Fresh ingredients

• Limes
• Lemons

Classic upgrade bottles

These are the bottles used in the classic versions, but I would not start here unless you already have them or know you love this style of drink.

A note on gin

Tanqueray is easy to find, reasonably priced, and strong enough to work well in shaken cocktails. It is a very good choice for the starter versions in this section.

My personal preference is Plymouth Gin. Plymouth is softer and rounder than Tanqueray, which makes these drinks feel a little more polished to me. If you are just starting out, use Tanqueray with confidence. If you already know you like gin cocktails, or you want to make the version closer to my personal taste, use Plymouth.

1. Last Word

The Last Word is the drink that creates the template for this section: base spirit, herbal liqueur, sweet liqueur, and citrus — all in equal parts.

It is bright, tart, herbal, and memorable. It is also one of the easiest cocktails to make that still feels like something from a serious cocktail bar.

Starter version

• ¾ oz gin, preferably Tanqueray London Dry or Plymouth
• ¾ oz Dolin Genepy
• ¾ oz Luxardo Maraschino
• ¾ oz fresh lime juice

Shake with ice and strain into a coupe.

Classic version

• ¾ oz gin
• ¾ oz Green Chartreuse
• ¾ oz maraschino liqueur
• ¾ oz fresh lime juice

Why it works

The gin gives structure, the lime keeps it sharp, the maraschino adds sweetness and depth, and the herbal liqueur makes the drink distinctive.

2. Naked & Famous

The Naked & Famous takes the Last Word idea and moves it toward mezcal, Aperol, and lime. It is smoky, bittersweet, citrusy, and bold.

Starter version

• ¾ oz Banhez Ensamble mezcal
• ¾ oz Aperol
• ¾ oz Dolin Genepy
• ¾ oz fresh lime juice

Shake with ice and strain into a coupe.

Classic version

• ¾ oz mezcal
• ¾ oz Aperol
• ¾ oz Yellow Chartreuse
• ¾ oz fresh lime juice

Why it works

Mezcal brings smoke, Aperol adds bittersweet orange, lime keeps the drink fresh, and the herbal liqueur ties everything together.

3. Monte Cassino

The Monte Cassino moves the same equal-parts idea into whiskey and lemon. It is warmer, richer, and more herbal.

Starter version

• ¾ oz Wild Turkey 101 bourbon
• ¾ oz Dolin Genepy
• ¾ oz Bénédictine D.O.M.
• ¾ oz fresh lemon juice

Shake with ice and strain into a coupe.

Classic version

• ¾ oz rye whiskey
• ¾ oz Yellow Chartreuse
• ¾ oz Bénédictine
• ¾ oz fresh lemon juice

Why it works

The whiskey gives the drink warmth, the lemon adds brightness, and the herbal liqueurs make it layered and memorable.

Rye is the more traditional choice, but bourbon works well for the starter version, especially if you want one whiskey bottle that will also be useful in later sections.

Section 2: More from the First Bottles

Before buying more spirits and liqueurs, I like to ask one question:

What else can we make with the bottles we already have?

Section 1 gave us a strong starting point: gin, mezcal, whiskey, maraschino, Aperol, Bénédictine, and an herbal liqueur. This section stretches that first set of bottles by adding simple syrups, fresh ingredients, bitters, and ginger beer.

The drinks here are less about rare bottles and more about learning how small changes create very different cocktails. Gin with lime and sugar becomes a Gimlet. Add mint and it becomes a Southside. Gin with lemon and honey becomes a Bee’s Knees. Use the same honey with whiskey and you have a Gold Rush.

This is the kind of section I like because it makes the first shopping list feel useful. The bottles from The Trio are not one-drink bottles. They become the beginning of a small but flexible home bar.

Shopping List

This section reuses bottles from Section 1 and adds a few simple ingredients.

Reused from Section 1

These are the ingredients from Section 1 that are used again in this section.

Fresh ingredients reused from Section 1

• Limes
• Lemons

New additions for Section 2

Syrups

Simple syrup

Combine equal parts sugar and warm water. Stir until dissolved.

Honey syrup

Combine 2 parts honey with 1 part warm water. Stir until dissolved.

Agave syrup

Combine 2 parts agave nectar with 1 part warm water. Stir until dissolved.

1. Gimlet

The Gimlet is one of the simplest gin cocktails: gin, lime, and sugar.

It is sharp, clean, and very easy to make. After the Last Word, it also shows how useful gin and lime can be even without herbal liqueur or maraschino.

Recipe

• 2 oz gin
• ¾ oz fresh lime juice
• ¾ oz simple syrup

Shake with ice and strain into a coupe.

Why it works

The Gimlet is the basic gin-and-lime sour template. It is not complicated, but it teaches balance very clearly: too much lime and it becomes harsh; too much syrup and it becomes flat. When the balance is right, it is crisp and refreshing.

Gimlet variation: Southside

A Southside is basically a Gimlet with mint.

Recipe

• 2 oz gin
• ¾ oz fresh lime juice
• ¾ oz simple syrup
• 6–8 mint leaves

Shake with ice and strain into a coupe.

You can also serve it tall with soda water if you want a lighter version.

Why it works

This is one of the easiest ways to see how a single fresh ingredient can change a cocktail. The structure is still gin, lime, and sugar, but the mint makes it colder, greener, and more refreshing.

2. Bee’s Knees

The Bee’s Knees is a gin sour with honey.

I like including it here because honey changes the character of a sour without making the drink more complicated. It adds aroma, texture, and a softer kind of sweetness than simple syrup.

Recipe

• 2 oz gin
• ¾ oz fresh lemon juice
• ¾ oz honey syrup

Shake with ice and strain into a coupe.

Why it works

Honey gives the drink more body than simple syrup. With gin and lemon, it becomes bright, floral, and easy to like.

It is also a useful drink to learn before the Gold Rush, because the next cocktail uses the same lemon-and-honey idea with whiskey instead of gin.

3. Gold Rush

The Gold Rush is one of the easiest whiskey cocktails to love. It is basically a Whiskey Sour with honey instead of simple syrup.

Recipe

• 2 oz bourbon or rye
• ¾ oz fresh lemon juice
• ¾ oz honey syrup

Shake with ice and strain into a rocks glass over ice, or serve up in a coupe.

Why it works

Whiskey and honey are a natural match. The lemon keeps the drink bright, while the honey makes it rounder and richer than a basic sour.

Seen next to the Bee’s Knees, it also shows how much the base spirit matters:

• Bee’s Knees = gin, lemon, honey
• Gold Rush = whiskey, lemon, honey

Same structure, completely different mood.

4. Whiskey Sour

Once you understand the Gold Rush, you are very close to a Whiskey Sour. The structure is almost the same, but the honey syrup is replaced with simple syrup.

Recipe

• 2 oz bourbon or rye
• ¾ oz fresh lemon juice
• ¾ oz simple syrup

Shake with ice and strain into a rocks glass over ice, or serve up in a coupe.

Optional:

• Egg white, for texture
• 2 dashes Angostura bitters, for aroma

Why it works

The Whiskey Sour is the basic whiskey-citrus-sugar template. It is less floral than a Bee’s Knees, less rich than a Gold Rush, and more direct than a Monte Cassino.

Egg white version

If using egg white, shake the ingredients without ice first, then add ice and shake again. This creates a smoother, foamier drink.

5. Kentucky Buck

The Kentucky Buck is a tall whiskey drink with lemon, strawberry, ginger beer, and bitters.

It is one of my favorite ways to show that whiskey cocktails do not always have to feel heavy. This one is bright, spicy, fruity, and refreshing.

Recipe

• 2 oz bourbon or rye
• ¾ oz fresh lemon juice
• ½ oz simple syrup
• 1 strawberry
• 2 dashes Angostura bitters
• Ginger beer, to top

Muddle the strawberry in a shaker. Add whiskey, lemon juice, simple syrup, bitters, and ice. Shake, then strain into a tall glass over ice. Top with ginger beer.

Why it works

The strawberry gives the drink fruit without making it overly sweet. The ginger beer adds spice and length. The bitters make the drink feel more complete.

If the Gold Rush is whiskey in a clean sour format, the Kentucky Buck is whiskey in a tall refreshing format.

6. Mezcal Tommy’s Margarita

This is a simple mezcal sour with lime and agave syrup.

I like it here because it gives mezcal another role after the Naked & Famous. Instead of smoky, bitter, and herbal, this drink is direct and agave-forward.

Recipe

• 2 oz mezcal
• 1 oz fresh lime juice
• ½ oz agave syrup

Shake with ice and strain into a rocks glass over ice.

Optional: add a salt rim, or a tiny pinch of salt to the shaker.

Why it works

This version does not use orange liqueur. That keeps the drink focused on the mezcal, lime, and agave. It is simple, sharp, smoky, and very easy to remember.

7. Hemingway’s Cats

Hemingway’s Cats is a mezcal riff in the Hemingway Daiquiri family. It uses mezcal, lime, grapefruit, maraschino, agave, and — in the full version — black lemon bitters.

I like it here because it reuses two important bottles from Section 1: mezcal and maraschino. But it does not feel like another Naked & Famous. The grapefruit moves it in a drier, brighter direction, while the agave keeps the drink tied naturally to the mezcal.

Starter version

• 2 oz mezcal
• ½ oz Luxardo Maraschino
• ½ oz fresh lime juice
• ½ oz fresh grapefruit juice
• ½ oz agave syrup

Shake with ice and strain into a coupe.

Original version

• 2 oz mezcal
• ½ oz maraschino liqueur
• ½ oz fresh lime juice
• ¼ oz fresh grapefruit juice
• ½ oz agave syrup
• 2 dashes Scrappy’s Black Lemon Bitters

Shake with ice and strain into a coupe.

My usual adjustment

I usually increase the grapefruit juice to ½ oz. I like the extra brightness, and it makes the drink feel more refreshing without moving too far away from the original structure.

Bitters note

The starter version can omit the bitters, but they are recommended if you have them. The black lemon bitters help improve the balance and make the citrus feel more complete.

Why it works

Mezcal gives the drink smoke and structure. Grapefruit adds bitterness and freshness. Maraschino gives sweetness and a subtle cherry-almond note. Agave rounds the drink out and connects naturally with the mezcal.

It also sets up a useful comparison for later: when we add rum, we can make the Hemingway Daiquiri and see how the same citrus-maraschino idea changes with a different base spirit.

Section 3: More Shaken Classics

Section 1 started with the trio: three equal-parts herbal cocktails that I personally love.

Section 2 showed how much more we could do with those first bottles by adding syrups, fruit, bitters, and ginger beer.

Now we add a few classic cocktail workhorses: orange liqueur, cognac or aged pisco, tequila, rum, and orgeat. These bottles open the door to more shaken classics: Sidecar, White Lady, Margarita, Daiquiri, Hemingway Daiquiri, Mai Tai, and Champs-Élysées.

I like this section because it makes the home bar feel much more complete without changing the basic idea of the guide. We are still mostly working with the same pattern: spirit, citrus, sweetness, and balance.

Shopping List

This section reuses some ingredients from the previous sections and adds a few new bottles.

Reused from Section 1

These are the Section 1 ingredients used again in this section.

Fresh ingredients reused from Section 1

• Limes
• Lemons

Reused from Section 2

These are the Section 2 ingredients used again in this section.

New additions for Section 3

Optional ingredients

Bottle notes

Orange liqueur

Cointreau is the easiest recommendation here. It is clean, strong, and useful in many classic cocktails.

This section uses it in the Sidecar, White Lady, Margarita, and Mai Tai. That makes it one of the most important additions so far.

Cognac or aged pisco

I group these together because they can fill a similar role in cocktails, even though they come from different traditions.

Cognac is a brandy made from wine grapes and aged in oak barrels, which gives it its characteristic color, texture, and notes of vanilla, spice, dried fruit, and oak. It is the classic choice for drinks like the Sidecar and Champs-Élysées.

Chilean aged pisco shares some of those qualities. Like cognac, it is distilled from grapes, and many Chilean piscos are rested or aged in wood barrels before bottling. That barrel aging softens the spirit and adds color and oak-derived flavors that make it feel closer to a young brandy than to the clear, unaged style of pisco many people know.

This is different from the Peruvian pisco most commonly found in liquor stores outside South America. Peruvian pisco is typically not aged in wood and is generally bottled clear, with the focus on preserving the fresh grape character of the distillate. Chilean aged pisco, by contrast, can develop richer notes of caramel, vanilla, dried fruit, and spice from time spent in barrel.

Because both cognac and Chilean aged pisco are grape-based spirits with some degree of barrel influence, they work surprisingly well in the same cocktail structures. They are not interchangeable in a strict historical sense, but if you enjoy grape spirits and citrus-forward drinks, aged Chilean pisco is an excellent alternative.

For cognac, Pierre Ferrand 1840 is a great cocktail bottle. It has enough body to work in Sidecars and other shaken drinks without feeling too precious to mix. For aged Chilean pisco, my favorite recommendation is Mistral Añejado en Roble, or another golden/oak-aged Mistral. It has the oak influence and richness that work especially well in these recipes.

The downside is that Mistral can be harder to find outside Chile than a good cognac. For Chilean readers, though, it is a very practical option since bottles like Mistral are widely available and often already part of the home bar. In the United States, Alto del Carmen is usually easier to find and can also work very well in these cocktails.

If you are choosing between the two, I would treat them as equally valid options rather than as a primary bottle and a substitute. Pierre Ferrand 1840 is an excellent cognac for cocktails, while an aged Chilean pisco such as Mistral brings its own character and value. Pick whichever is easier to find, fits your budget, or sounds more appealing to your palate.

Rum

Rum can get complicated very quickly. For this section, I would split it into two bottles:

• White rum, for the Daiquiri, Hemingway Daiquiri, and part of the Mai Tai
• Blended or aged rum, for the Mai Tai

You can technically make all the rum drinks with one bottle, but the Mai Tai is much better with a more flavorful split base. Since this guide is still trying to build the bar gradually, I would start with one white rum first, then add the blended or aged rum when you are ready to make the Mai Tai properly.

For white rum, Planteray 3 Stars is a good starter bottle. It is affordable, easy to find, and has more character than a neutral white rum. My preferred upgrade is Probitas, especially for Daiquiris.

For the blended or aged rum, Appleton Estate Signature is the practical starter choice. It is flavorful, widely available, and brings enough Jamaican character to work well in a Mai Tai. Denizen Merchant’s Reserve is the upgrade if the Mai Tai becomes important to you.

1. Sidecar

The Sidecar is one of the essential shaken classics: cognac, orange liqueur, and lemon.

It fits naturally here because it introduces two important bottles at once: cognac and orange liqueur. It is elegant, bright, and simple.

Recipe

• 2 oz cognac or aged Chilean pisco
• ¾ oz Cointreau
• ¾ oz fresh lemon juice
• 1 tsp simple syrup

Shake with ice and strain into a coupe.

Optional: sugar rim.

Why it works

The Sidecar is a grape-spirit sour. Cognac gives it richness, lemon keeps it sharp, and orange liqueur sweetens while adding citrus aroma.

The teaspoon of simple syrup makes the drink just a touch rounder and softer. Aged Chilean pisco will not make a traditional Sidecar, but it works beautifully in the same structure. It keeps the drink grape-based, bright, and elegant.

2. White Lady

The White Lady takes the same basic idea as the Sidecar and moves it to gin.

It is gin, orange liqueur, and lemon: lighter, sharper, and more botanical.

Recipe

• 2 oz gin, preferably Plymouth
• ½ oz Cointreau
• ¾ oz fresh lemon juice
• ¼ oz simple syrup
• 1 egg white, optional

Shake without ice first if using egg white, then add ice and shake again. Strain into a coupe.

Why it works

The White Lady shows why orange liqueur is such a useful bottle. With cognac and lemon, it gives you a Sidecar. With gin and lemon, it gives you something brighter and more delicate.

Egg white gives the drink a silkier texture, but you can omit it for a simpler starter version.

3. Margarita

The Margarita is the tequila member of the classic sour family: tequila, orange liqueur, and lime.

It also gives us a useful contrast with the Mezcal Tommy’s Margarita from Section 2.

Recipe

• 2 oz tequila blanco
• ¾ oz Cointreau
• ¾ oz fresh lime juice

Shake with ice and strain into a rocks glass over ice.

Optional: salt rim, or a tiny pinch of salt in the shaker.

Why it works

The Section 2 Mezcal Tommy’s Margarita was mezcal, lime, and agave. This version uses tequila and orange liqueur, so it feels brighter and more classic.

Both drinks are useful because they show two different ways to build an agave sour.

4. Daiquiri

The Daiquiri is one of the cleanest shaken classics: rum, lime, and sugar.

It is simple, but not boring. A good Daiquiri is one of the best ways to understand balance.

Recipe

• 2 oz white rum
• ¾ oz fresh lime juice
• ¾ oz simple syrup

Shake with ice and strain into a coupe.

Why it works

There is nowhere to hide in a Daiquiri. The rum, lime, and sugar have to be in balance. When they are, the drink is crisp, refreshing, and much more elegant than its reputation sometimes suggests.

5. Hemingway Daiquiri

The Hemingway Daiquiri builds on the Daiquiri with grapefruit and maraschino.

I like including it here because it connects directly to Hemingway’s Cats from Section 2.

Recipe

• 1½ oz white rum
• ½ oz Luxardo Maraschino
• 1 oz fresh grapefruit juice
• ½ oz fresh lime juice
• 1 tsp simple syrup

Shake with ice and strain into a coupe.

Why it works

This drink makes a useful comparison:

• Hemingway’s Cats = mezcal, lime, grapefruit, maraschino, agave
• Hemingway Daiquiri = rum, lime, grapefruit, maraschino, simple syrup

The structure is similar, but the base spirit changes the whole personality of the drink. Mezcal makes it smoky and dry. Rum makes it brighter and rounder.

6. Mai Tai

The Mai Tai is a classic from the tiki family, but here I think of it simply as another great shaken cocktail: rum, lime, orange liqueur, and orgeat.

It fits this section because it uses two of the new additions: rum and orange liqueur. It also introduces orgeat, which gives the drink its almond richness.

Recipe

• 1 oz blended or aged rum, such as Appleton Estate Signature
• 1 oz white rum
• ¼ oz Cointreau
• 1 oz fresh lime juice
• ¾ oz orgeat
• 1 dash Angostura bitters

Shake with ice and strain into a rocks glass over crushed ice or regular ice.

Optional: garnish with mint or a spent lime shell.

Why it works

If the Daiquiri is the cleanest rum sour, the Mai Tai is richer and nuttier. The orgeat adds texture and almond flavor, while the orange liqueur adds citrus depth.

The split rum base makes the drink more layered without making it too complicated: the white rum keeps it bright, while the blended or aged rum gives it more body and character.

7. Champs-Élysées

If the Sidecar is the clean cognac sour, the Champs-Élysées is the herbal version.

I like it here because it connects Section 3 back to Section 1. We added cognac or aged pisco for the Sidecar, and now we can combine it with the herbal liqueur from The Trio.

Starter version

• 2 oz cognac or aged Chilean pisco
• ½ oz Dolin Genepy
• ¾ oz fresh lemon juice
• ¼ oz simple syrup
• 1 dash Angostura bitters

Shake with ice and strain into a coupe.

Classic version

Use Green Chartreuse instead of Genepy.

Why it works

Cognac or aged pisco gives the drink richness, lemon keeps it bright, and the herbal liqueur adds complexity.

It is a good example of how one new bottle can connect with an older one and make the whole bar feel more useful.

Section 4: Vermouth and Stirred Classics

So far, most of the drinks in this guide have been shaken with citrus. That makes sense for a beginner path: citrus drinks are bright, forgiving, and easy to understand.

This section moves into vermouth and stirred cocktails.

Stirred drinks feel different. They are usually stronger, smoother, and more spirit-forward. Instead of balancing spirit with citrus, we are now balancing spirit with vermouth, bitters, sugar, bitter aperitivo, herbal liqueurs, and dilution.

The main new bottles here are sweet vermouth, dry vermouth, Campari, and blended Scotch. With those, plus bottles we already have, we can make some of the most important stirred classics and variations:

• Negroni
• Boulevardier
• Manhattan
• Old Fashioned
• Gin Martini
• Joy Division
• Monte Carlo
• Bobby Burns

I like this section because it changes the rhythm of making drinks. No shaking, no citrus pressing, no foam. Just spirits, ice, stirring, and a very different kind of balance.

Shopping List

This section reuses bottles from the previous sections and adds vermouth, Campari, Scotch, and a few stirred-drink extras.

Reused from Section 1

These are the Section 1 ingredients used again in this section.

Fresh ingredients reused from Section 1

• Lemons (for garnish twists)

Reused from Section 2

These are the Section 2 ingredients used again in this section.

Reused from Section 3

These are the Section 3 ingredients used again in this section.

New additions for Section 4

Optional ingredients

Bottle notes

Sweet vermouth

Sweet vermouth is one of the bottles that unlocks this section. It shows up in the Manhattan, Negroni, Boulevardier, and Bobby Burns.

For a starter bottle, Dolin Rouge is a good choice: lighter, not too expensive, and easy to use. Cocchi Vermouth di Torino is richer and also an excellent option.

My personal preference is Carpano Antica Formula. It is fuller, more vanilla-forward, and more luxurious. It can make stirred cocktails feel deeper and more rounded, especially Manhattans and Boulevardiers.

Sweet vermouth should be stored in the refrigerator after opening. It is wine-based, so it will not last forever like spirits do.

Dry vermouth

Dry vermouth is what opens the door to the Martini and Joy Division.

For a starter bottle, Dolin Dry is a good choice. It is easy to find, not too expensive, and useful in many Martini-style drinks. As with sweet vermouth, store it in the refrigerator after opening.

Campari

Campari is the classic bitter red aperitivo for the Negroni and Boulevardier.

Aperol can make softer, sweeter versions of those drinks, and that can be useful if someone is not used to bitterness. But for this section, I would add Campari. It is more bitter, more intense, and it gives these drinks their classic profile.

Blended Scotch

Scotch enters the guide here because it gives Bénédictine another useful role in the Bobby Burns, and it will also be reused later in Sin Cyn.

For this guide, I would use blended Scotch. You do not need an expensive single malt for these drinks. A blended Scotch gives you enough malt character to make the cocktail work without making the bottle feel too precious to mix.

Famous Grouse is a good starter bottle. Johnnie Walker Red Label is a practical starter alternative, especially if it is easier to find. My recommendation is Monkey Shoulder. It is still approachable, but it has more body and malt character than many entry-level blends, which helps in stirred drinks with vermouth, Bénédictine, or Cynar.

I would avoid starting with a heavily smoky Scotch here. If you want smoke later, you can add a small rinse or float of peated Scotch instead of making the whole drink smoky.

Absinthe

Absinthe is powerful, so I would not buy it early. In this section, it is here for the Joy Division, where only a few dashes are enough.

A bottle of absinthe lasts a long time because most cocktails use it in tiny amounts: a rinse, a dash, or a few drops.

1. Negroni

The Negroni is one of the most important stirred cocktails: gin, Campari, and sweet vermouth in equal parts.

It is bitter, herbal, slightly sweet, and very easy to remember.

Recipe

• 1 oz gin
• 1 oz Campari
• 1 oz sweet vermouth

Stir with ice, then strain into a rocks glass over fresh ice.

Garnish with an orange peel or orange slice.

Softer starter variation

If Campari feels too bitter at first, use Aperol instead.

• 1 oz gin
• 1 oz Aperol
• 1 oz sweet vermouth

This is not a classic Negroni, but it is a good way to learn the structure before moving to Campari.

Why it works

The Negroni is all about tension. Gin gives it structure, Campari brings bitterness, and sweet vermouth rounds everything out. It is simple on paper, but the flavor is bold and memorable.

2. Boulevardier

The Boulevardier is the whiskey cousin of the Negroni.

The starter version uses the same equal-parts structure, which makes it easy to remember. Gin makes the Negroni crisp and botanical. Whiskey makes the Boulevardier warmer, richer, and deeper.

Starter version

• 1 oz bourbon or rye
• 1 oz Campari
• 1 oz sweet vermouth

Stir with ice, then strain into a rocks glass over fresh ice or into a coupe.

Garnish with an orange peel.

My preferred adjustment

Once you know the drink, I prefer making it a little more whiskey-forward:

• 1½ oz bourbon or rye
• ¾ oz Campari
• ¾ oz sweet vermouth

This keeps the same basic shape, but gives the whiskey more room.

Softer starter variation

If you are still getting used to Campari, you can try Aperol first:

• 1 oz bourbon or rye
• 1 oz Aperol
• 1 oz sweet vermouth

It will be sweeter and less bitter, but still useful for understanding the structure.

Why it works

The Boulevardier shows how much a cocktail can change when only one ingredient changes. The Negroni and Boulevardier both use bitter aperitivo and sweet vermouth, but whiskey makes the drink feel fuller and more autumnal.

Bourbon makes it rounder and sweeter. Rye makes it drier and spicier.

3. Manhattan

The Manhattan is one of the essential whiskey cocktails: whiskey, sweet vermouth, and bitters.

Where the Boulevardier uses bitterness from Campari, the Manhattan uses just a small amount of Angostura bitters. That makes it more focused on the whiskey and vermouth.

Recipe

• 2 oz rye or bourbon
• 1 oz sweet vermouth
• 2 dashes Angostura bitters

Stir with ice, then strain into a coupe.

Garnish with a cocktail cherry.

Why it works

The Manhattan is strong but smooth. The whiskey gives the drink structure, the vermouth adds sweetness and depth, and the bitters pull everything together.

Rye is the classic direction if you want the drink drier and spicier. Bourbon makes it softer and sweeter.

4. Old Fashioned

The Old Fashioned is the simplest stirred whiskey cocktail: whiskey, sugar, bitters, and ice.

It does not require sweet vermouth or Campari, but I like it in this section because it teaches the same stirred-drink mindset. There is no citrus to hide behind. The drink is about spirit, sweetness, bitters, and dilution.

Recipe

• 2 oz bourbon or rye
• 1 tsp simple syrup, or 1 sugar cube
• 2 dashes Angostura bitters

Stir with ice in a rocks glass.

Garnish with an orange peel.

Why it works

The Old Fashioned is not trying to transform the whiskey. It is trying to season it. Sugar softens the spirit, bitters add aroma and spice, and ice slowly brings everything into balance.

This is also a good place to notice how much dilution matters. A rushed Old Fashioned can feel hot and sharp. A properly stirred one becomes smoother, colder, and more integrated.

5. Gin Martini

The Martini is one of the most important stirred cocktails, and also one of the most personal. Small changes in gin, vermouth, dilution, garnish, and ratio can make it feel like a completely different drink.

For this guide, I would start with a version that is dry, but not extreme.

Recipe

• 2 oz gin, preferably Plymouth
• ¾ oz dry vermouth
• 1 dash orange bitters, optional

Stir with ice, then strain into a chilled coupe or Nick & Nora glass.

Garnish with a lemon twist or olive.

Why it works

The Martini is not about hiding the gin. It is about shaping it. Dry vermouth softens the gin, adds texture, and brings a subtle herbal wine note. The result should be cold, clean, and balanced rather than just strong.

Beginner note

Do not start with an ultra-dry Martini. A little more vermouth makes the drink easier to understand and usually better balanced.

6. Joy Division

The Joy Division is a modern Martini variation with gin, dry vermouth, Cointreau, and absinthe.

I like it here because it connects several parts of the guide: gin from the first section, orange liqueur from Section 3, and the stirred Martini structure from this section.

Recipe

• 2 oz gin, preferably Plymouth
• 1 oz dry vermouth
• ½ oz Cointreau
• 3 dashes absinthe

Stir with ice, then strain into a chilled coupe or Nick & Nora glass.

Garnish with a lemon twist.

Why it works

The Joy Division starts from a Martini-like structure but adds two strong accents: orange liqueur and absinthe. Cointreau adds brightness and sweetness, while absinthe adds an aromatic anise note. The result is still crisp and stirred, but more expressive than a classic Martini.

7. Monte Carlo

The Monte Carlo is a simple stirred whiskey drink with Bénédictine and bitters.

I like it here because it gives Bénédictine another use after the Monte Cassino, and it fits naturally with the stirred drinks in this section. If the Old Fashioned is whiskey, sugar, and bitters, the Monte Carlo is whiskey, Bénédictine, and bitters.

Recipe

• 2 oz rye or bourbon
• ½ oz Bénédictine
• 2 dashes Angostura bitters

Stir with ice, then strain into a rocks glass over a large ice cube.

Garnish with a lemon twist.

Why it works

Bénédictine brings sweetness, honey, spice, and herbal depth. It does the job of a sweetener, but with much more character than plain sugar.

Rye is especially good here because its spice keeps the drink from becoming too sweet. Bourbon works too, but the drink will be rounder and softer.

8. Bobby Burns

The Bobby Burns is a Scotch, sweet vermouth, and Bénédictine cocktail.

I like it here because it gives both Bénédictine and Scotch a clear role in the guide. If the Manhattan is whiskey and sweet vermouth with bitters, the Bobby Burns moves that idea toward Scotch and herbal sweetness.

Recipe

• 1 oz blended Scotch
• 1 oz sweet vermouth
• ½ oz Bénédictine

Stir with ice, then strain into a coupe.

Garnish with a lemon twist.

Why it works

The Scotch gives the drink malt and structure. Sweet vermouth adds body and richness. Bénédictine brings honey, spice, and herbal depth.

A starter blended Scotch is completely fine here. Use Famous Grouse or Johnnie Walker Red if you want an accessible bottle. Use Monkey Shoulder if you want a more polished version.

Optional: Manhattan, Boulevardier, and Monte Carlo comparison

If you like whiskey drinks, the Manhattan, Boulevardier, and Monte Carlo are worth thinking about together.

They all start from whiskey, but the modifier changes the entire drink:

• Manhattan = whiskey, sweet vermouth, bitters
• Boulevardier = whiskey, sweet vermouth, Campari
• Monte Carlo = whiskey, Bénédictine, bitters

The Manhattan is smoother and more spirit-forward. The Boulevardier is more bitter, richer, and more dramatic. The Monte Carlo is sweeter, more herbal, and closer to an Old Fashioned with extra complexity.

This kind of comparison is one of the best ways to learn cocktails. You are not memorizing random recipes; you are seeing how one ingredient changes the entire shape of a drink.

Section 5: Amaro and the Circle Back

At this point, the guide has moved through equal-parts herbal drinks, simple sours, shaken classics, and stirred cocktails.

Now I want to add amaro.

Amaro can be confusing because there are many bottles and they all taste different. Some are bright and citrusy, some are dark and rich, some are vegetal, and some are intensely bitter. But I do not think you need to understand the whole category at once.

For this section, I want to start with a few amari that unlock specific cocktails:

• Amaro Montenegro, as the starter amaro
• Amaro Nonino, as the Paper Plane upgrade
• Averna, as the Black Manhattan upgrade
• Cynar, for darker and more vegetal drinks

What I like about this section is that it completes a circle.

We started with The Trio, especially the Last Word template: a base spirit, a herbal or bitter component, a sweet liqueur, and citrus. The Paper Plane and Oh My Word! bring us back to that same idea, but with amaro now part of the language.

Not every drink in this section follows the Last Word template, and that is fine. The point is not to force every cocktail into the same structure. The point is to show how amaro can either bring us back to the beginning, or take the bottles we already have into a deeper, more bitter direction.

Shopping List

Reused from Section 1

These are the Section 1 ingredients used again in this section.

Fresh ingredients reused from Section 1

• Lemons

Reused from Section 2

These are the Section 2 ingredients used again in this section.

Reused from Section 4

These are the Section 4 ingredients used again in this section.

New additions for Section 5

Optional ingredients

Bottle notes

Amaro Montenegro

Amaro Montenegro is the starter amaro for this section. It is lighter, more floral, and more orange-forward than many darker amari.

I like using Montenegro first because it gives us several useful drinks without immediately buying many different amaro bottles. It works in Oh My Word!, a starter Paper Plane, M&M, and a Montenegro Manhattan-style drink.

It will not perfectly replace Nonino or Averna, but it lets you understand the structure before upgrading.

Amaro Nonino

Amaro Nonino is the classic upgrade for the Paper Plane.

Montenegro makes a very good starter version: lighter, more floral, and approachable. Nonino makes the drink richer, deeper, and closer to the version most people think of when they talk about a Paper Plane.

If the Paper Plane becomes one of your favorite drinks, Nonino is the upgrade.

Averna

Averna is the upgrade for a Black Manhattan.

A Montenegro Manhattan-style drink is a good starting point, but Averna makes the drink darker, richer, and more cola-like. That is the direction people usually expect from a Black Manhattan.

Cynar

Cynar is darker, more vegetal, and more savory. It is often described as artichoke-based, but it does not taste like drinking artichokes. It is bittersweet, earthy, and surprisingly flexible.

I like Cynar in this section because it shows a different side of amaro. Montenegro and Nonino connect us back to brighter, more aromatic cocktails. Cynar moves us toward something deeper and more bitter.

Lime bitters

Lime bitters are not a general-purpose beginner bottle, but they are important for Oh My Word! because the drink is a citrus-free Last Word riff.

Instead of using fresh lime juice, it uses lime bitters to suggest lime while keeping the drink stirred and spirit-forward.

1. Paper Plane

The Paper Plane is one of the modern classics that most clearly connects back to the equal-parts idea from Section 1.

It uses bourbon, Aperol, amaro, and lemon in equal parts. That makes it easy to remember, but the flavor is much more interesting than the recipe suggests.

Starter version

• ¾ oz bourbon
• ¾ oz Aperol
• ¾ oz Amaro Montenegro
• ¾ oz fresh lemon juice

Shake with ice and strain into a coupe.

Classic upgrade

• ¾ oz bourbon
• ¾ oz Aperol
• ¾ oz Amaro Nonino
• ¾ oz fresh lemon juice

Shake with ice and strain into a coupe.

Why it works

The Paper Plane feels like a cousin of the Naked & Famous. Both are equal-parts drinks. Both use Aperol and citrus. But where the Naked & Famous uses mezcal and herbal liqueur, the Paper Plane uses bourbon and amaro.

That shift changes the mood of the drink. It becomes warmer, rounder, and more bittersweet, while still staying bright and refreshing.

This is one of the reasons I like the equal-parts template so much. Once you understand the shape, you can see how changing one or two ingredients creates a completely different cocktail.

2. Oh My Word!

Oh My Word! is a stirred, citrus-free riff on the Last Word.

I like placing it here because it makes the circle back to Section 1 very explicit. The Last Word started the guide with gin, herbal liqueur, maraschino, and lime. Oh My Word! keeps the Last Word spirit, but moves it into a darker, more bitter, more spirit-forward direction.

Recipe

• ¾ oz gin
• ¾ oz Amaro Montenegro
• ¾ oz Bénédictine
• ¾ oz maraschino liqueur
• 2 dashes lime bitters

Stir with ice and strain into a coupe or Nick & Nora glass.

Why it works

Oh My Word! is not just another Last Word variation. It changes the format. Instead of being shaken with fresh citrus, it is stirred and built around liqueurs and bitters.

The gin gives structure. Montenegro adds bittersweet orange and floral notes. Bénédictine brings sweetness and herbal depth. Maraschino adds its familiar cherry-almond character. Lime bitters point back to the original Last Word without using actual lime juice.

It feels like a later-stage version of the same idea: more bitter, more aromatic, and more contemplative.

3. M&M

The M&M is almost too simple to call a cocktail: mezcal and Amaro Montenegro in equal parts.

I like it here because it gives Montenegro another use and connects it to mezcal from Section 1. It is smoky, bittersweet, herbal, and very easy to remember.

Recipe

• 1 oz mezcal
• 1 oz Amaro Montenegro

Stir with ice and strain into a small rocks glass over ice, or serve as a small chilled drink.

Optional: orange twist.

Why it works

Mezcal brings smoke and structure. Montenegro brings orange, herbs, sweetness, and bitterness. Together they make a tiny two-bottle drink that feels much more complete than it should.

4. Montenegro Manhattan

This is not a traditional Black Manhattan, but it is a good starter version if Montenegro is the amaro you already bought for this section.

Recipe

• 2 oz rye or bourbon
• 1 oz Amaro Montenegro
• 2 dashes Angostura bitters
• Optional: 1 dash orange bitters

Stir with ice and strain into a coupe.

Garnish with an orange twist or cherry.

Classic upgrade: Black Manhattan

Use Averna instead of Montenegro.

Averna makes the drink darker, richer, and closer to the classic Black Manhattan profile.

Why it works

The Manhattan from Section 4 used whiskey, sweet vermouth, and bitters. This version keeps the whiskey and bitters, but replaces vermouth with amaro.

Montenegro makes the drink lighter and more orange-forward. Averna makes it darker, richer, and more intense.

5. In Cold Blood

In Cold Blood is a simple stirred Cynar cocktail: whiskey, sweet vermouth, and Cynar.

It is especially useful here because it connects Section 4 and Section 5. From Section 4, we already have whiskey and sweet vermouth. By adding Cynar, we get a darker, more vegetal variation in the same broad family as a Boulevardier or Manhattan.

Recipe

• 1 oz rye whiskey
• 1 oz sweet vermouth, preferably Carpano Antica Formula
• 1 oz Cynar

Stir with ice and strain into a rocks glass over a large ice cube.

Optional: garnish with a lemon twist and a tiny pinch of salt.

Why it works

In Cold Blood is rich, bitter, and simple. The rye gives spice, the sweet vermouth gives body, and Cynar adds an earthy bitterness that makes the drink feel darker and more savory.

The pinch of salt is small, but useful. It can make the drink feel more focused and bring the bitter and sweet parts together.

6. Sin Cyn

Sin Cyn is another equal-parts Cynar cocktail, but this time with Scotch.

It is part Rob Roy, part Boulevardier, and very easy to remember: Scotch, sweet vermouth, and Cynar.

Recipe

• 1 oz blended Scotch
• 1 oz sweet vermouth, preferably Carpano Antica Formula
• 1 oz Cynar

Stir with ice and strain into a rocks glass over fresh ice, or serve up in a coupe.

Optional: garnish with an orange twist.

Why it works

The Scotch changes the drink completely. Compared with In Cold Blood, Sin Cyn is less spicy and more malty. Cynar adds bitterness, sweet vermouth adds richness, and the whole drink becomes round, dark, and herbal.

A blended Scotch is a good starting point here. Use Famous Grouse or Johnnie Walker Red if you want an accessible bottle, or Monkey Shoulder if you want the drink to feel more polished.

7. Smoke Show

Smoke Show brings Cynar into a shaken mezcal drink.

This one does not follow the equal-parts template, and that is part of why I like it here. It shows that amaro is not only for stirred drinks or Paper Plane-style formulas. It can also work as a small but powerful modifier in a sour.

Starter version

• 2 oz mezcal
• ¼ oz Cynar
• ¼ oz Dolin Genepy
• ½ oz fresh lemon juice
• ½ oz simple syrup
• 1 egg white, optional

Shake with ice and strain into a coupe. If using egg white, shake without ice first, then add ice and shake again.

Optional: garnish with freshly grated cinnamon.

Classic upgrade

Use Green Chartreuse instead of Genepy.

Why it works

Smoke Show layers smoke, bitterness, herbs, citrus, and texture. Mezcal gives the drink its base. Cynar adds earthy bitterness. Genepy or Green Chartreuse adds a high herbal note. Lemon and syrup keep it in sour territory.

The cinnamon garnish is optional, but it gives the drink a warm aroma that works very well with mezcal and Cynar.

Optional: Amaro highballs

Amaro does not always need a full cocktail.

If you want an easy way to use the bottles in this section, try them with tonic or soda over ice.

Monte & Tonic

• 2 oz Amaro Montenegro
• Tonic water, to top
• Orange slice or twist

Cynar & Soda

• 2 oz Cynar
• Soda water, to top
• Lemon or orange twist

These are not the focus of the guide, but they are useful because they let you taste the amaro more directly.