Cocktail barSports bar$$$kenmore-fenwayMon-Thu 11:30-24:00, Fri-Sat 11:30-02:00, Sun 11:30-22:00
Bleacher Bar on Lansdowne Street sits beneath the centre-field bleachers at Fenway Park in Boston's Kenmore Square since 2008. Located in Kenmore Fenway.
Signature drink: Pint of Sam Adams Boston Lager
Food: Pub food and burgers
Tip: Reservations on the website during Sox games; arrive 2 hours before first pitch. The garage-door window opens onto the field on rainouts.
Cocktail barTapas bar$$$south-endMon-Sat 17:00-23:00, closed Sunday
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.
Signature drink: Spanish gin and tonic with juniper
Food: Spanish tapas
Tip: Happy hour 17:00-19:00 weekdays runs half-price tapas. The lounge is the walk-in seat; book the dining room for parties.
Cocktail barCocktail bar$$$beacon-hillSun-Thu 17:00-01:00, Fri-Sat 16:00-02:00
Yvonne's reopened the historic Locke-Ober space on Winter Place in Downtown Boston in 2015 as a modern supper club. Order the aviation cocktail.
Signature drink: Aviation cocktail
Food: Globe-trotting small plates
Tip: The library room is the quiet cocktail seat. Sunday and Monday nights are the easy walk-in slots.
Cocktail barCocktail bar$$$beacon-hillMon-Wed 17:00-01:00, Thu-Sat 17:00-02:00, Sun 17:00-23:00
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.
Signature drink: Charles Street Manhattan
Food: Snacks
Tip: The jail-cell booths book up by 19:00 on weekends. The bar lounge is the easier walk-in seat.
Cocktail barCocktail bar$$$beacon-hillTue-Sat 17:00-21:00, closed Sun-Mon
The Gin Palace at Nine on Park Street is the cocktail bar inside the new Nine restaurant on Beacon Hill in Boston since August 2025. 80 gins from around.
Signature drink: Gin and Tonic with global gins
Food: Steak tartare and bar bites
Tip: Walk-in bar at the front; reservations for the dining room. Order the Gin and Tonic flight to compare three gins.
Cocktail barEspresso bar$$$north-endDaily 08:00-24:00
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.
Signature drink: Grappa and espresso
Food: Italian pastry
Tip: Basement liquor bar after 21:00 is the under-toured seat. Grappa and espresso is the canonical close.