A date plan
Date · Williamsburg · Romantic
Start the evening with minimal-intervention wines and oysters at a laid-back Bedford Ave wine bar, move into a candlelit Italian dinner, and finish with fifth-generation Puglian gelato eaten outside on Wythe.
Williamsburg · $$$ · Wine bar
With Others is exactly what a first stop should be: low-key enough to actually talk, interesting enough to give you something to talk about. The wine list is all minimal-intervention stuff — cloudy, funky, alive — and the small plates (get the oysters) make it easy to linger without committing to a full meal. Pull up a seat, order something orange, and let the night find its shape.
~7 min walk (0.3 mi). From With Others on Bedford, head south toward Grand Street — it's a quick, pleasant walk through the heart of Williamsburg's low-key residential blocks. Notice the mix of old-school bodegas and new wine bars coexisting peacefully.
Williamsburg · $$$ · Restaurant · Cocktail bar
Have & Meyer is the rare Italian spot that earns the word 'intimate' without being cramped about it — warm lighting, thoughtful sustainable sourcing, and a menu that leans into handmade pastas and honest flavors. The sidewalk seating is a flex on a good night, but inside is where the candles do their work. Order the pasta, share everything, and don't skip the wine list just because you already had a glass down the street.
~9 min walk (0.4 mi). After dinner, stroll from Havemeyer Street over to Wythe Ave — the avenue has a nice buzz on weekend evenings, with plenty of people-watching to accompany the walk. Gelateria Gentile is just a few blocks up Wythe; you'll want to eat outside, so pick your side of the street strategically based on the breeze.
Williamsburg · $$ · Ice cream shop · Store
Gelateria Gentile has been making gelato in Puglia since 1880, and the Williamsburg outpost doesn't coast on that backstory — the fondente is deeply, seriously chocolatey, and the pistachio is the real thing. Get two scoops, add the house panna (their traditional whipped cream, made in-house), and take it outside onto Wythe. The whole city feels more manageable from this particular corner.