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Cocktail barSports barKenmore Fenway
Bleacher Bar on Lansdowne Street sits beneath the centre-field bleachers at Fenway Park in Boston's Kenmore Square since 2008. Located in Kenmore Fenway.
DrinkPint of Sam Adams Boston Lager
FoodPub food and burgers
TipReservations on the website during Sox games; arrive 2 hours before first pitch. The garage-door window opens onto the field on rainouts.
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Cocktail barTapas barSouth End
Julio de Haro's Estragon on Harrison Avenue has poured Spanish gin-tonics and tapas in Boston's South End since 2008. Boston Magazine Best of Boston 2023.
DrinkSpanish gin and tonic with juniper
FoodSpanish tapas
TipHappy hour 17:00-19:00 weekdays runs half-price tapas. The lounge is the walk-in seat; book the dining room for parties.
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Cocktail barCocktail barBeacon Hill
Yvonne's reopened the historic Locke-Ober space on Winter Place in Downtown Boston in 2015 as a modern supper club. Order the aviation cocktail.
DrinkAviation cocktail
FoodGlobe-trotting small plates
TipThe library room is the quiet cocktail seat. Sunday and Monday nights are the easy walk-in slots.
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Cocktail barCocktail barBeacon Hill
Alibi inside the Liberty Hotel on Charles Street has run a former-jail-cell cocktail bar in Beacon Hill Boston since 2007. Order the charles street manhattan.
DrinkCharles Street Manhattan
FoodSnacks
TipThe jail-cell booths book up by 19:00 on weekends. The bar lounge is the easier walk-in seat.
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Cocktail barCocktail barBeacon Hill
The Gin Palace at Nine on Park Street is the cocktail bar inside the new Nine restaurant on Beacon Hill in Boston since August 2025. 80 gins from around.
DrinkGin and Tonic with global gins
FoodSteak tartare and bar bites
TipWalk-in bar at the front; reservations for the dining room. Order the Gin and Tonic flight to compare three gins.
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Cocktail barEspresso barNorth End
Caffe Vittoria on Hanover Street has poured espresso and grappa in Boston's North End since 1929. Four floors, three liquor bars, a cigar room.
DrinkGrappa and espresso
FoodItalian pastry
TipBasement liquor bar after 21:00 is the under-toured seat. Grappa and espresso is the canonical close.