Fool's Errand

By Eric Twardzik   Fenway · Cocktails · $$

Who’d have thought a standing-room-only bar trading in sherry and vermouth could be found in the shadow of Fenway Park?

Tiffani Faison did. You can thank the empire-building local chef for the existence of this self-styled “adult snack bar”—though describing it as a bar feels generous. It’s closer in size to a walk-in closet, albeit one with fabulous chandeliers, funky toile wallpaper, and an envious supply of sherry and fortified wines. Place your order and compete for space at the U-shaped bar or at the drink rails along the wall. Alternatively, take in the air (as the seasons allow) at a marble communal table on the micro-sized patio.

Wherever you land, a parade of tiny bites will follow. Salty slices of Benton’s ham with peaches; a mille-feuille oozing raclette cheese; bite-sized beef tongue “Fancy Finger Sammies” topped with crushed Lays and speared with toothpicks: This is the perfect fare to nosh as you sip a dry fino and wonder whether pre-dinner is becoming dinner-dinner.

Any of the vermouths on the menu can be served on the rocks, with tonic, with a splash of soda, or neat.

Seasonal cocktail specials and featured wines are written on the inside mirror.

Feeling fancy? You can add Island Creek caviar atop any dish on the menu (2 grams minimum).

Must Haves

  • This low-ABV Negroni riff swaps gin for dry, creamy palo cortado sherry, becoming the perfect aperitif cocktail in the process.

  • Sweet and bitter with complex notes of fruit and vanilla, this cognac-based aperitif is worth sipping neat.

  • This crisp, dry sherry is the perfect foil for the rich snacks that come from the kitchen.

Fun Fact

Fool’s Errand is one of four Tiffani Faison restaurants in a two-block radius: It’s sandwiched between the barbecue-based Sweet Cheeks Q and the Southeast Asian-focused Tiger Mama, and just up the street from her Italian-American spot Orfano (and makes a fine first stop before dinner at any of them).

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