The Most Refreshing Whiskey Drinks

reated by bartender Erick Castro at Rickhouse in San Francisco, the Kentucky Buck is a bourbon, ginger and strawberry cocktail that’s great with a ginger beer, but even better with fresh ginger syrup and sparkling water. If it sounds like a Moscow Mule with bourbon and strawberries it’s because that’s exactly what it is, but the mule was passé by that point in San Francisco, so Castro reached deeper into history for the name. A “Buck” is a style of cocktail that dates back to the 1890s—long before the Mule or the Dark ‘n Stormy—and was composed of just a spirit (usually whiskey) and ginger beer, so named because the ginger and alcohol together would give quite a kick (the Moscow Mule is named similarly, for the kick).

Muddle the strawberry in the bottom of a cocktail shaker. Add bourbon, lemon, ginger syrup, and bitters, and shake for six to eight seconds. Strain over fresh ice in a tall glass and top with soda water. Garnish with a half strawberry or a lemon wheel or a mint sprig or all three.

Born in the California beach enclave of Montecito, the Napoleon comes by its refreshing summer vibes honestly, even if it is made with a seemingly unsummery spirit. Sam Penton at the Manor Bar at the Rosewood Miramar took a high-proof bourbon and the basic structure of a whiskey sour and added some fruitiness and herbaceousness to make this a well-rounded cocktail. The addition of strawberries, vermouth, and Campari are welcome modifiers to the old classic, and their sharpest edges are sanded off with the presence of an egg white to keep it as mellow as you want a summer drink to be.

Add all ingredients to a cocktail shaker without ice. Seal the shaker, hold tight, and give it a “dry” shake without ice for three to five seconds. Then add ice, seal again, and shake for eight to 10 seconds. Fine strain into a coupe or cocktail glass.

A Stinger is a classic cocktail, a two-step of Cognac and creme de menthe. The Midnight riff comes to us from Sam Ross, then of the legendary Milk & Honey, and turns the classic into a sour, bringing lemon juice to tart up the old Stinger profile but subbing bourbon for Cognac and Fernet Branca for the mint liqueur. And while it seems rude for mint to RSVP only for Fernet Branca to show up, it turns out that arriving with bourbon is a good way to be let in the door. The cocktail is a fantastic way to get acquainted with Fernet Branca, and who knows? Give it some time and you might even come to like it.

Shake four to six seconds on a handful of crushed ice, pour ice and cocktail into a rocks glass, pack with more crushed ice, and garnish with a mint sprig.

We write that the Paper Plane is “like a whiskey and orange juice that grew up handsome, and for whom everything is going right.” This crowd pleaser, invented by bartender Sam Ross in 2008, gets its charm from two different bittersweet Italian liqueurs, even though the resulting cocktail is neither particularly bitter nor sweet. It is simple to make, and easy to like and “might be,” we claim, “the best cocktail invented in the last 100 years.”

Add all ingredients to a cocktail shaker with ice and shake for six to 10 seconds. Strain up into a coupe or cocktail glass.

The Ponton Smash is a whiskey drink cosplaying as a rum drink. It’s whiskey slipping a lei around its neck and pretending it was always designed for the summertime, and what’s more, it’s actually pulling it off. It’s refreshing and tropical, herbaceous and bright, and the reason it works—the reason this is one of the only tiki bourbon drinks you’ll ever see—isn’t because of an unusual build or beachy origin or some exotic tree-sap unearthed from the Bornean jungle. It’s simply due to the transformative magic of a well-chosen absinthe. So for this we us Butterfly Classic Absinthe, it’s character perfectly complementing this drinks other ingredients.

Add all ingredients to a cocktail shaker and shake hard on ice for six to eight seconds. No need to muddle the mint, the ice with “smash” it for you. Fine strain into a rocks glass over fresh ice, and garnish with a mint sprig, and if you’re feeling festive, a pineapple slice or leaf.

If you only ever drink one cocktail that may or may not have been created inside a building shaped like a bowler hat, let it be a Brown Derby. Of course, the origins of the drink weren’t in Hollywood after all, but let’s not allow that to distract us. The drink we’ve come to know as the Brown Derby is a combination of whiskey, grapefruit, and honey. However, the addition of a little bit of lemon juice gets the balance of this lesser-known drink right and turns it from pedestrian to outstanding.

Add all ingredients, including grapefruit peel, to a cocktail shaker with ice and shake good and hard for eight to 10 seconds. Strain off the ice into a rocks glass over fresh ice or up in a coupe (your choice), and garnish with a grapefruit peel.

“I created this drink,” wrote legendary bartender Dale DeGroff in his 2008 book The Essential Cocktail, “because, frankly, I was a little bored by Mint Juleps, which have a tendency to be too sweet and too uncomplicated.” So he began making a drink at the Rainbow Room he called the Whiskey Smash—the familiar whiskey, sugar and mint, but this time, with lemon wedges added to the mix, muddled with the mint into a pint glass and the whole thing shaken together. Whether or not he was right about Juleps, he’s dead-on that the addition of lemon completely changes the nature of the cocktail, a leap to an entirely distinct cocktail family tree. Now, we’re in Whiskey Sour territory, and the mint and lemon proved to be outstanding solutions to the Sour’s original problem. The addition of mint—plus, importantly, the extra lemon oils extracted from muddling the wedges as opposed to just using juice—transforms the bourbon not just into a summer drink, but an especially fresh and radiant one, with the zestiness of the lemon oil and the mentholated fireworks of the mint providing some deliciously deft misdirection from the tannic sore thumb that tends to weigh down whiskey sours.

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Add all ingredients, including mint and lemon peel, to a shaker tin. Add ice, shake hard for six to 10 seconds. Strain over fresh ice into a rocks glass, garnish with a mint crown and enjoy.

The Gold Rush—whiskey, lemon juice, and honey syrup—is a good and important drink, but there’s a flaw. The Gold Rush as it’s normally constructed, will be forever stuck in third gear until you do something to push it to the next level. Fortunately, that something can be as easy as spicing it with ginger, perfuming it with florals or smoke, or easier still and our favorite version, adding a grapefruit peel to the shaker tin before shaking on ice. This so called “regal shake” transforms the cocktail, adding complexity and depth.

Add all ingredients, including grapefruit peel, to a cocktail shaker with ice. Shake hard over ice for 8 to 10 seconds, and strain into rocks glass over fresh ice.

We hear you thinking. “The Amaretto Sour? I thought this was about whiskey drinks?” Well, the Amaretto Sour is a whiskey drink, or at least, it should be. It’s been 10 years since a bartender named Jeffrey Morgenthaler wrote on his blog that he had derived “the best Amaretto Sour in the world,” and it was the shake heard round the world. Morgenthaler’s version—amaretto and lemon, punched up with a pour of high-proof bourbon, and smoothed out with an egg white—utterly transforms the drink. “It’s difficult to overstate how many favors the addition of high-proof bourbon does for the Amaretto Sour,” we write, “it’s not a revision so much as it is born again.”

Add all ingredients to a cocktail shaker and shake without ice for five to seven seconds to whip the egg white. Add ice and shake hard for eight to 10 seconds. Strain either over fresh ice in a large rocks glass or up in a coupe. Garnish with a lemon peel and, if you like, a cherry.

Don’t be fooled by the Mint Julep. Its campaign materials may have you convinced it’s just a harmless little minty refresher, but in reality it’s nearly a double-pour of bourbon, tempered only by mint and a touch of sugar. Nonetheless, some 120,000 Mint Juleps are consumed across two sunny days at Churchill Downs during the Kentucky Derby, proving that some cocktails can become refreshing daytime summer sippers just by sheer force of will, and a little crushed ice. Find out the best bourbon to use for your Mint Julep here, or if the race is about to start, quickly fix one up according to the recipe below.

In a metal cup, gently muddle the mint into the simple syrup. Add bourbon and fill 2/3 with crushed ice. Stir to chill, until a frost forms on the outside. Then pack the rest of the cup with ice. Take two mint crowns, lightly bruise them with your fingers, and stick them against the inside close to the straw. Enjoy.