Cocktail barEspresso bar$$$north-endDaily 08:00-24:00
Caffe Vittoria on Hanover Street has poured espresso and grappa in Boston's North End since 1929. Four floors, three liquor bars, a cigar room.
Signature drink: Grappa and espresso
Food: Italian pastry
Tip: Basement liquor bar after 21:00 is the under-toured seat. Grappa and espresso is the canonical close.
Cocktail barBrewpub$$$seaport-fort-pointMon-Fri 12:00-23:00, Sat 11:00-23:00, Sun 11:00-22:00
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.
Signature drink: Trillium IPA
Food: Brewpub menu
Tip: Third-floor roof seats fill by 17:00 in summer. Online order ahead for can release lineups.
Cocktail barBeer hall$$$seaport-fort-pointMon-Thu 12:00-21:00, Fri-Sat 12:00-22:00, Sun 12:00-18:00
Harpoon Brewery's Beer Hall on Northern Avenue in Boston's Seaport has poured pints since 1986. Located in Seaport Fort Point. Order the harpoon ipa.
Signature drink: Harpoon IPA
Food: Beer hall pretzel and brats
Tip: Saturday tour at 13:00 includes the full brewery and four pours. The hot pretzel is the kitchen signature.
Cocktail barCocktail bar$$$beacon-hillDaily 17:00-02:00
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.
Signature drink: Absinthe Sazerac
Food: Snacks and bar bites
Tip: Find the unmarked door inside the wig storefront.
Cocktail barCocktail bar$$$somervilleTue-Sun 17:00-23:15, closed Monday
Backbar in Union Square Somerville has poured artful cocktails behind an unmarked door in Boston since 2011. Order the greek mastiha milk punch.
Signature drink: Greek mastiha milk punch
Food: Snacks
Tip: Walk-in only, no reservations. Last call 23:15. Order from the staff-pick chalkboard for the best off-menu drink.
Cocktail barSports bar$$$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.