The Sunset Tavern on Ballard Avenue runs live music seven nights a week in a vintage red room, with Betty's Room as the front bar and Flying Squirrel Pizza on the menu next door.
Tip: Most shows kick off at 21:00. Cash and card both work; the front bar stays open even when the back room is between sets.
Address: 5433 Ballard Avenue NW, Seattle, WA 98107
The Triple Door on Union Street is the 250 seat dinner theater across from Benaroya Hall, with table service, an Asian small plates menu and bookings across jazz, soul, world and cabaret.
Tip: Reserve a table at booking; the Mainstage runs two sets nightly with seated dining. Musicquarium Lounge in the lobby is free.
The Nest at the Thompson Seattle hovers above Stewart Street with 360 degree views of Elliott Bay and the Olympics, a geodesic Rain Drop dome and seasonal couches around fireplaces.
Tip: 21 plus, cashless. Check in with the host downstairs at the hotel lobby for the elevator key. Happy hour 16:00 to 17:00 and 21:00 to 22:00 Sun to Thu.
Smith Tower Observatory Bar sits 35 floors above Pioneer Square inside the 1914 Smith Tower, with a speakeasy era cocktail program on the wraparound observation deck.
Tip: Admission ticket includes entry to the observation deck plus the bar. Reserve via the Smith Tower site; the deck is open 360 degrees in good weather.
Frolik on the 5th floor of the Motif Seattle is the largest year round rooftop in downtown, with a 4,000 square foot terrace, fire pit bars, ping pong and curling lanes in winter.
Tip: Igloos and curling open from November. Walk in friendly weekdays; reserve via OpenTable for weekend brunch and Thursday to Saturday evenings.
Goldfinch Tavern at the Four Seasons opens its terrace bar alongside the hotel's infinity pool, looking out over the Great Wheel and Puget Sound. Live jazz with Brian Nova Thursday through Saturday.
Tip: Reserve dinner via OpenTable; the bar runs the same hours and is the easier walk in. Sip Champagne after sunset from the pool side.
Canon on 12th Avenue is Jamie Boudreau's Capitol Hill cocktail room with the largest spirits library in the country at 4,000 plus labels and a strict four guest cap per party.
Tip: Open Wednesday through Sunday from 17:00 to 00:00. Walk in friendly, limited reservations; the bar caps parties at four to keep service tight.