A date plan
Date · West Village · Adventurous · $$
An adventurous evening that moves from a candlelit wine bar to a family-run Italian with tableside theater, then drops underground for live jazz to close the night.
West Village · $$ · Bar · Italian restaurant
Aria Wine Bar on Bedford Street is exactly the kind of place you stumble onto and never forget — low ceilings, exposed brick, and a wine list curated entirely from female vintners. Pull up to the bar and let them walk you through a pour while you graze on small plates. The room does the flirting for you.
~2 min walk (0.1 mi). From Aria, head north on Bedford Street and cut through the neighborhood's quietest, prettiest blocks — keep an eye out for the gas lamps on Grove Street, one of the few remaining in the city. It sets the mood perfectly for Ferdi just around the corner.
West Village · $$$ · Italian restaurant
Ferdi is a 44-seat labor of love — three generations of the Scarpati family, from the Bronx's Grand Concourse to the Rainbow Room to this warm West Village room with exposed brick and candlelight. Order the reds (the whites play it safe) and save room for the tableside liquid-nitrogen gelato, which is genuinely the most fun you can have over dessert without leaving your chair. Make a reservation — this place earns its full room every night.
~6 min walk (0.3 mi). Ferdi to Smalls is a short stroll up 7th Ave South to West 10th Street. The neighborhood gets a little livelier as you move — let the sound of the city shift gears before you head underground into the club.
West Village · $$ · Jazz club · Bar
Smalls Jazz Club is the West Village's best-kept loud secret: a tiny, no-frills basement room where serious jazz happens nightly and the energy crackles. Grab a spot, order a drink, and let the music take over the conversation for a while — in the best possible way. Late-night jam sessions can run past 2am, so you don't have to call it early unless you want to.