Lookout Rooftop and Bar ★ 4.4
$$$$
$18 cocktails, upscale casual dress, reservations advisedSeaport Fort PointMon-Wed 16:00-23:00, Thu 16:00-00:00, Fri 16:00-01:00, Sat 12:00-01:00, Sun 12:00-23:00.
Lookout at the Envoy Hotel sits seven stories above the Seaport with a wraparound terrace facing the harbor and the Fort Point Channel. Heated igloos extend.
TipReserve via OpenTable for a guaranteed table; walk-in lines build by 18:00 in summer. Igloos book months ahead from October.
Rooftop at Revere ★ 4.0
$$$$
$18 cocktails, seasonal May to September onlyBeacon HillMon-Thu 16:00-22:00, Fri 16:00-23:00, Sat 12:00-23:00, Sun 12:00-22:00.
Rooftop at Revere on the Revere Hotel roof is the largest rooftop lounge in Boston, with two outdoor bars, plush cabanas and a panorama from Boston Common.
TipSeasonal opening usually late April, runs to late September. Reserve via SevenRooms for cabanas; walk-in seating fills by 18:00.
Contessa ★ 4.5
$$$$
$22 cocktails, smart dress, reservations essentialBack BayMon-Wed 06:30-22:00, Thu-Fri 06:30-23:00, Sat 07:00-23:00, Sun 07:00-22:00.
Contessa on the 17th floor of The Newbury Boston runs a glass-roof conservatory with retractable panels above the Public Garden. Italian small plates.
TipAperitivo Hour Sunday to Wednesday 17:00-18:00 runs discount Negronis and bar snacks. Resy is essential for dinner.
The Wig Shop ★ 4.5
$$$$
Beacon HillDaily 17:00-02:00.
The Wig Shop on Temple Place hides a basement cocktail lounge behind a fake Downtown Crossing wig storefront with neon signage and mannequin heads.
TipReservations on Resy 17:00-19:00 for parties of 2 to 6. Walk-in after 19:00; absinthe drip service is the order.
Yvonne's ★ 4.4
$$$$
Beacon HillMon-Thu 17:00-01:00, Fri-Sat 16:00-02:00, Sun 17:00-01:00.
Yvonne's on Winter Place revived the 19th century Locke-Ober supper-club space in 2015 with a hidden door inside a fake hair salon, a library room.
TipLibrary is the quiet seat for cocktails; reserve the Gallery weeks ahead. Sunday and Monday are the walk-in nights.
Offsuit ★ 4.6
$$$$
ChinatownTue-Thu 17:00-01:00, Fri-Sat 16:00-01:00. Closed Mon/Sun.
Offsuit hides inside the French bistro Troquet on South on Utica Street. Twenty seats, no signage, alley door, a cocktail menu built around the bartenders.
TipCall from the door rather than knock. Reserve via Resy or join the wait list from the alley side after 17:00.