A date plan
Date · Greenwich Village · Casual · $$
A casually romantic Greenwich Village evening that moves from a legendary cocktail den to a candlelit Tuscan table, finishing with gelato and a chocolate fountain on Bleecker.
Greenwich Village · $$ · Cocktail bar · Bar
The Up & Up is the kind of basement bar that makes you forget the city exists above it. Slip into one of the banquettes, let your eyes adjust to the low light, and order whatever the bartender is clearly proud of — the cocktail list rewards the curious. It's intimate without being precious, which is exactly the right energy to start a night.
~6 min walk (0.3 mi). From The Up & Up, head south on MacDougal and hang a right onto Bleecker — the stretch between 6th Ave and 7th Ave South is one of the great NYC strolls. Peek into the record stores and old storefronts as you make your way toward I Sodi.
Greenwich Village · $$$ · Tuscan restaurant
I Sodi is compact, romantic, and resolutely Tuscan — the kind of place where a shared plate of pappardelle and a bottle of Chianti does all the heavy conversational lifting for you. The room is warm and close in the best possible way, and the regulars here clearly know something the rest of the city doesn't. Go for the pasta, linger over the wine.
~4 min walk (0.2 mi). After dinner, you're practically already there — Venchi is just a short walk east on Bleecker. Take the slow route and window-shop the boutiques along the way. Note: I Sodi and Venchi are on the West Village end of Bleecker, a touch west of the Greenwich Village core, but this is a seamless, walkable strip — no neighborhood whiplash whatsoever.
Greenwich Village · Chocolate shop · Ice cream shop
End the night at Venchi, a Turinese chocolate house tucked into the old Grom space on Bleecker — where crêpes are dressed straight from a chocolate fountain and the gelato comes in a proper waffle cone. Order the pistachio, stand close, and don't skip the hot chocolate if the night has any chill in it. Open until midnight on weekends, so there's no rush.