The Cantab Lounge ★ 4.4
$cambridge{'monday': '17:00-01:00', 'tuesday': '17:00-23:00', 'wednesday': '17:00-01:00', 'thursday': '17:00-02:00', 'friday': '17:00-02:00', 'saturday': '17:00-02:00', 'sunday': '17:00-01:00'}
The Cantab Lounge in Central Square has run live music seven nights a week since 1938. Two floors: a folk-and-jazz street-level lounge and the Cantab Underground downstairs for rock, funk and DJs.
Tip: Bluegrass Tuesdays from 20:00, started 1993, $6 cover. Sundays bring a Boston Poetry Slam in the Underground.
Lookout Rooftop and Bar ★ 4.4
$$$$18 cocktails, upscale casual dress, reservations advisedseaport-fort-point{'monday': '16:00-23:00', 'tuesday': '16:00-23:00', 'wednesday': '16:00-23:00', 'thursday': '16:00-00:00', 'friday': '16:00-01:00', 'saturday': '12:00-01:00', 'sunday': '12:00-23:00'}
Lookout at the Envoy Hotel sits seven stories above the Seaport with a wraparound terrace facing the harbor and the Fort Point Channel. Heated igloos extend the season through winter.
Tip: Reserve via OpenTable for a guaranteed table; walk-in lines build by 18:00 in summer. Igloos book months ahead from October.
Rooftop at Revere ★ 4.0
$$$$18 cocktails, seasonal May to September onlybeacon-hill{'monday': '16:00-22:00', 'tuesday': '16:00-22:00', 'wednesday': '16:00-22:00', 'thursday': '16:00-22:00', 'friday': '16:00-23:00', 'saturday': '12:00-23:00', 'sunday': '12:00-22:00'}
Rooftop at Revere on the Revere Hotel roof is the largest rooftop lounge in Boston, with two outdoor bars, plush cabanas and a panorama from Boston Common across Back Bay to the Charles.
Tip: Seasonal opening usually late April, runs to late September. Reserve via SevenRooms for cabanas; walk-in seating fills by 18:00.
Contessa ★ 4.5
$$$$$22 cocktails, smart dress, reservations essentialback-bay{'monday': '06:30-22:00', 'tuesday': '06:30-22:00', 'wednesday': '06:30-22:00', 'thursday': '06:30-23:00', 'friday': '06:30-23:00', 'saturday': '07:00-23:00', 'sunday': '07:00-22:00'}
Contessa on the 17th floor of The Newbury Boston runs a glass-roof conservatory with retractable panels above the Public Garden. Italian small plates and aperitivo menu run through dinner service.
Tip: Aperitivo Hour Sunday to Wednesday 17:00 to 18:00 runs discount Negronis and bar snacks. Resy is essential for dinner.
The Wig Shop ★ 4.5
$$$beacon-hill{'monday': '17:00-02:00', 'tuesday': '17:00-02:00', 'wednesday': '17:00-02:00', 'thursday': '17:00-02:00', 'friday': '17:00-02:00', 'saturday': '17:00-02:00', 'sunday': '17:00-02:00'}
The Wig Shop on Temple Place hides a basement cocktail lounge behind a fake Downtown Crossing wig storefront with neon signage and mannequin heads. Deep blue banquettes, gold curtains, absinthe service.
Tip: Reservations on Resy 17:00 to 19:00 for parties of 2 to 6. Walk-in after 19:00; absinthe drip service is the order.
Yvonne's ★ 4.4
$$$beacon-hill{'monday': '17:00-01:00', 'tuesday': '17:00-01:00', 'wednesday': '17:00-01:00', 'thursday': '17:00-01:00', 'friday': '16:00-02:00', 'saturday': '16:00-02:00', 'sunday': '17:00-01:00'}
Yvonne's on Winter Place revived the 19th century Locke-Ober supper-club space in 2015 with a hidden door inside a fake hair salon, a library room and a 24-seat Gallery accessed behind a bookshelf.
Tip: Library is the quiet seat for cocktails; reserve the Gallery weeks ahead. Sunday and Monday are the walk-in nights.