Bleacher Bar on Lansdowne Street sits beneath the centre-field bleachers at Fenway Park in Boston's Kenmore Square since 2008. Live view of the field through a one-way window, sports-bar food.
Food program: 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.
Address: 82 Lansdowne St, Boston, MA 02215
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; all-Spanish wine list.
Signature drink: Spanish gin and tonic with juniper
Food: Spanish tapas
Tip: Happy hour 17:00 to 19:00 weekdays runs half-price tapas. The lounge is the walk-in seat; book the dining room for parties.
Yvonne's reopened the historic Locke-Ober space on Winter Place in Downtown Boston in 2015 as a modern supper club. Late-night kitchen, library room, the hidden door inside a fake hair salon.
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.
Alibi inside the Liberty Hotel on Charles Street has run a former-jail-cell cocktail bar in Beacon Hill Boston since 2007. The hotel building was the Charles Street Jail from 1851 to 1990.
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.
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 the world; cocktail-led drinks programme.
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.
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; the city's first Italian cafe-bar.
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.
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; hazy IPAs, lagers, kitchen runs to 22:00.
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.
