A date plan
Date · Upper West Side · Fun & Playful · $$
Start with wine and small bites at a neighborhood gem, move to a fun karaoke-friendly bar for some playful bonding, and finish with Italian chocolate bliss.
Upper West Side · $$$ · Wine bar
This intimate wine bar is the perfect opening act for a romantic evening—think candlelit corners and a thoughtfully curated wine list that won't break the bank. The staff knows their stuff and loves pairing wines with small bites; order the charcuterie and let the romance simmer.
~0.8 mi — consider a cab or the subway. Walking from Vanguard to e's BAR, you'll drift down Amsterdam Ave—watch for the side streets to open up and catch the neighborhood energy shift as you head deeper into the heart of the UWS. It's a short, scenic hop.
Upper West Side · $$ · Cocktail bar · Bar & grill
This spirited bar is where fun goes to live—with karaoke, craft cocktails, and a kitchen slinging small plates that actually hit. The vibe is playful without being rowdy, making it the ideal place to laugh together, maybe even grab the mic if you're feeling brave.
~0.8 mi — consider a cab or the subway. From e's BAR to Venchi, double back toward Columbus Ave. You'll pass the bustle of the neighborhood's dining scene, and by the time you hit Venchi, you've done a nice little loop that keeps you in the best pocket of the UWS.
Upper West Side · $$ · Ice cream shop · Chocolate shop
End on the sweetest note with Venchi's luxe Italian gelato and handmade chocolate—this is the spot that turns a good date into an unforgettable one. The pistachio is legendary, but honestly, sharing a dark chocolate scoop off one spoon is peak romance.