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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.
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Cocktail barBrewpubSeaport Fort Point
Trillium on Thomson Place is the Fort Point three-storey taproom and brewpub in Boston since 2018. The third-floor roof terrace is the marquee seat.
DrinkTrillium IPA
FoodBrewpub menu
TipThird-floor roof seats fill by 17:00 in summer. Online order ahead for can release lineups.
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Cocktail barBeer hallSeaport Fort Point
Harpoon Brewery's Beer Hall on Northern Avenue in Boston's Seaport has poured pints since 1986. Located in Seaport Fort Point. Order the harpoon ipa.
DrinkHarpoon IPA
FoodBeer hall pretzel and brats
TipSaturday tour at 13:00 includes the full brewery and four pours. The hot pretzel is the kitchen signature.
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Cocktail barCocktail barBeacon Hill
The Wig Shop has run a speakeasy-style cocktail bar behind a fake wig-shop storefront on Temple Place in Downtown Boston since 2019. 1940s magazine-ad decor.
DrinkAbsinthe Sazerac
FoodSnacks and bar bites
TipFind the unmarked door inside the wig storefront.