A date plan
Hangout · Upper West Side
A loose, fun-filled Upper West Side crawl that hits a buzzy cocktail bar, a shareable-plates dinner made for groups, and a laid-back pub with board games and karaoke to close out the night.
Upper West Side · $$ · Cocktail bar
Kick things off at Arthouse Bar, the speakeasy-style lobby bar of the Arthouse Hotel where a live piano player sets a surprisingly cool mood. The sidewalk cafe is great for a warm night, but the moody interior is where the vibe really lives. Order a round of cocktails, get settled, and let everyone catch up before the night gets going.
~7 min walk (0.4 mi). Walking from Arthouse Bar to Ella Social, you'll pass a stretch of Columbus Ave with some solid window-shopping — keep an eye out for the occasional pop-up or street musician adding to the UWS sidewalk energy.
Upper West Side · $$$ · Spanish restaurant
Ella Social is the move for a group — the whole menu is built around shareable plates with Latin and Mediterranean flavors, which means nobody has to commit to just one thing. Housemade ingredients show up in the drinks too, so let the table go in on a pitcher or a round of their signature cocktails. It's lively enough to talk over each other, which is exactly what you want.
~14 min walk (0.7 mi). Ella Social to e's BAR takes you up Amsterdam Ave — it's a quick hop north, and the street gets a little quieter as you go, which makes it a nice beat to decompress between dinner and the next round.
Upper West Side · $$ · Cocktail bar · Bar & grill
End the night at e's BAR, a neighborhood pub with rotating drink specials, big windows, and — the secret weapon — board games and karaoke. This is the kind of place where a 'quick nightcap' turns into two hours without anyone noticing. Grab a cheap beer, pick a game off the shelf, or dare someone in the group to get up and sing.