Believe it or not, “New York Streets” is a local reference. It’s the name of a long-vanished South End neighborhood whose streets were named after communities in upstate New York. Razed in 1956, it’s been largely forgotten—but not by Lion’s Tail, the cocktail bar that sits at its former center and pays homage with this swizzle.

The tall drink looks like a party in a glass, but don’t underestimate its complexity. Its central element is a caramelized pineapple-infused gin, which managing partner Jarek Mountain makes using Plymouth Gin.

“It’s a very soft, balanced gin,” Mountain says. “Its alcohol content is high enough that it can pick up that flavor and suck the pineapple juice up.”

Also in the mix is the sweeter, floral style of bianco vermouth (which Mountain notes can be substituted with Cocchi Americano), bitter quinquina, and dry sherry. Lemon juice adds acidity, and mint simple syrup boosts the minty theme that’s mirrored in an extra-generous garnish.

As a swizzle drink, it’s only whip shaken, meaning that just one ice cube is used. “Anything over crushed ice, we whip. That way it’s not overly diluted,” Mountain says.

The swizzle itself is a two-step process. In the first instance, the glass is only filled halfway with crushed ice so that the swizzle motion won’t spill ice from the top. It’s filled to the top before the second swizzle, and finally crowned with a little more crushed ice to form a “dome” that can be dashed with Angostura bitters.

According to Mountain, swizzles can be viewed as the lo-fi forbearer of the blended drink. “Back in the day, before blenders, this is how they blended cocktails,” Mountain says.

New York Streets Swizzle
1½ ounces caramelized pineapple-infused Plymouth Gin*
1 ounce Alessio Vermouth Bianco
1 ounce lemon juice
1 ounce mint simple syrup**
½ ounce Kina l’Aéro d’Or Vin Apéritif au Quinquina
½ ounce dry sherry
8-10 mint leaves, plus extra 15-20 sprigs for garnish
4-5 dashes Angostura bitters

Add mint leaves and mint simple syrup to a pilsner glass. Gently muddle until mint becomes fragrant. Add remaining ingredients (except bitters) to a shaker with a single ice cube, and shake until the cube can no longer be heard rattling inside the tin. Pour contents of shaker into the pilsner glass, and then fill glass halfway with crushed ice. Use swizzle stick or bar spoon to swizzle ingredients with ice until the outside of the glass is chilled. Fill up the remainder of the glass with crushed ice, and swizzle again. Top with crushed ice, Angostura bitters, and mint sprigs.

*Caramelized Pineapple-Infused Plymouth Gin
1 750ml bottle Plymouth gin
¾ of a pineapple, peeled and diced
4 ounces pineapple juice
2 cinnamon sticks, halved

Add pineapple pieces to a hotel pan and bake at 350 degrees F for 10 to 15 minutes, or until pineapple begins to caramelize. Remove from oven, and immediately add pineapple to a container with all other ingredients. Steep until pineapple has reached room temperature (about 10 to 15 minutes) and seal container. Refrigerate overnight. The following day, strain into a container, muddling pineapple pieces to extract as much juice as possible. Keeps about 3 weeks, sealed and refrigerated.

**Mint Simple Syrup (yields about 1¼ cups)
8 mint leaves
1 cup sugar
1 cup water

Add mint and sugar to a saucepan and gently muddle to release oils. Once mint is fragrant, add water and set heat to medium. Cook for 10 to 15 minutes, stirring occasionally. Once the sugar has dissolved, remove from heat and strain into a sealed container. Keeps about 2 weeks, refrigerated.