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Local Libations: Five Island Old Fashioned

2011 November 18

by Pete Vasconcellos


New York, NY – After the recent run of beer posts, I’m picking the rum baton back up from Sarah’s Celebes Dream and carrying it forward in the form of an Old Fashioned.

The name “Old Fashioned” refers to what was once called simply the “Whiskey Cocktail.” This drink is the father of all cocktails: spirit, sweetener and bitters. Exact dates are hazy, but sometime around the late 1800s, the definition of ‘cocktail’ was broadened to refer to any number of mixed drinks, and the old-timers who wanted none of the new-fangled drinks would ask for an “old fashioned whiskey cocktail.” It was eventually shortened to just “Old Fashioned.”

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My idea of an Old Fashioned was the muddled orange peel and maraschino cherry drink ordered by old men who were cutting loose on a Friday night. The muddling of fruit probably started during Prohibition as a way to mask the taste of poor-quality booze. Including fruit became the norm, and a number of cocktail guides from the 1930s on (Mr. Boston being the most widely distributed) call for it. Today’s cocktail geeks have mostly returned to the old Old Fashioned, and skip the cherry altogether. Meanwhile, “Old Fashioned” has returned as a reference to a method of drink-making rather than a specific drink itself.

The Five Island Old Fashioned, therefore, is just such a drink with some of the ingredients swapped out. The drink gets its name from the spirit, Banks Five Island Rum. It is unique in that it is a blend of rums from Trinidad, Barbados, Jamaica, Guyana and Indonesia, which gives it an amazing layered character. The nose is at first floral and citrus, but then banana, earth and mushroom funk begin to surface (for the nerds, this funk has a name: “hogo“). Don’t let the clear look of the rum fool you. In the mouth you’ll find age, body and vegetal character that wants to be sipped neat or delicately adorned as in an Old Fashioned.

Bitters: Thanksgiving is less than a week away, so the coffee bitters I have adapted from this recipe are great for that quick turnaround (for a classic bitters recipe, see Jessie Chien’s Bitter Expat). I have been using Irving Farm’s Gotham Blend for my coffee and Rittenhouse 100 proof Bonded Rye for my base spirit. Because its proof is low for bitters, you have the luxury of letting it steep longer if you like, but five days is plenty. After messing around with combinations of bittering agents, I’ve found that a blend of quassia, wormwood and black walnut suits my palate. If you can get to the East Village in NYC, a great shop called Flower Power will sell you these roots and herbs in small quantities. A little goes a long way.

Sweetener: Granulated and Demerrara sugars lack the body to make this feel like an after-dinner quaff. For a cap to a cold-weather meal, Grade B maple syrup makes the Five Island rich and round. I generally use Deep Mountain Grade B from Vermont, which is sold at the Union Square Greenmarket. Grade B will always beat Grade A in an arm-wrestling match. It is much more rich and mirrors some of the earth flavors found in the Banks Rum. You only need a touch.

Big ice is recommended. A 2″ ice cube will melt slowly and evenly, allowing you time to sip without watering down your drink.

Five Island Old Fashioned

Prep Time (with bitters): 5 days

Active Prep Time: 1 minute

Yield: 1 cocktail

Tools: bitters – large jar, coffee filter/cheesecloth, fine-meshed sieve, measuring cups, digital scale, dropper or used bitters bottle for storage; cocktail – Mixing glass, bar spoon, julep strainer, peeler, jigger


  • 2 oz Banks Five Island Rum
  • 1 barspoon Grade B Vermont maple syrup
  • 3 dashes/2 droppers-full coffee bitters
  • Lemon Peel
  • Orange Peel

For the Coffee Bitters:

  • 375ml Rittenhouse 100 Proof Bonded Rye
  • Peel from one orange
  • 12 g Irving Farm Gotham Blend, coarsely ground with mortar and pestle
  • 1 sticks cinnamon
  • 1/4 star anise
  • 1 g black walnut
  • 1 g Quassia
  • 1 g Wormwood


  1. For the Bitters: Coarsely crush the coffee with a mortar and pestle. Fully peel a navel orange with as little pith possible. Combine the all the ingredients in a non reactive covered container and sit for at least five days. Agitate the mixture twice a day and check it for aroma. Remove the orange peels early if the aroma begins to dominate.
  2. Strain through a coffee filter or a fine cheesecloth.
  3. For the cocktail: combine rum, bitters and maple syrup in a mixing glass over ice. Stir gently for 30 seconds as not to crack the ice.
  4. Strain into over a big ice cube in a double old fashioned glass.
  5. Garnish with a lemon and orange twist. Express the peels, skin side down, over the drink before inserting them in the glass.

Pete Vasconcellos has been tending bar in Boston and New York for fifteen years. He has finally forgotten how to make a Malibu Bay Breeze.