Chelsea Date Ideas in New York

Curtained booths give Raines Law Room a private feel, which suits two people settling into a Prohibition-style speakeasy in Chelsea. Everyone has a seat, and you order drinks with a call button at your table. The setting feels like a genuine speakeasy rather than a themed one, and the curtains keep your conversation to the two of you. Reserve online before you go.

Walk the High Line at sunset for a romantic date above the traffic, with West Side views along the way. Up on the West Side, the High Line runs 1.5 miles above the street, with gardens and public art along the way. Enter at Gansevoort Street or 14th Street, then finish with dinner at Chelsea Market or in the West Village.

Green accents and an antique feel set the scene at Da Andrea Chelsea, an Italian restaurant in Chelsea with a big bar. Staff are glad to give wine advice, so you can lean on them when choosing a bottle together. Take a seat at the bar for a drink or settle in for dinner.

Little Island is a park open to the public, out on Pier 55 within Hudson River Park. It is built around nature, relaxation and views you can take in together, and you can explore the seasonal landscape on foot. Follow a guided audio tour with award-winning narrators, or wander without one and see what you find.

Tucked into Chelsea, Sanyuu West is a small sushi bar where the cozy seating keeps you and your date close while the omakase moves along quickly. The sake is good too, and we recommend pairing the omakase with a glass.

Sogno Toscano in Chelsea is a Tuscan-themed cafe that works as an espresso bar, a market and a wine bar. The wine bar gives the two of you a spot to share a glass, and the menu includes Burrata e Crudo with DOP burrata, Prosciutto di Parma, rucola and EVOO. The Tuscan theme runs through the cafe, so a coffee stop, a look around the market and a glass of wine can share one visit.

Sit at the omakase counter at Sushi Blossoms in Chelsea, where the room is lively and noisy. The dishes are fusion-style, and the sake list is strong, so a glass or a bottle fits naturally into the meal. The buzz makes it a good pick when you want a date with some energy.

Inventive cocktails are the draw at Twist Bar, a small bar in Chelsea. Easy bar seating lets the two of you sit side by side, while the outdoor seating gives you a second option for a drink outside. Pick two of the more inventive drinks and compare them together.

Txula Steak is a Spanish Basque restaurant with a retro look and a relaxed mood, and its about 25 tables keep the room on the small side. The small room and easy mood give the two of you a low-key place to settle in. The menu names croquettes and steak, and we recommend sharing both.

Tradition guides the menu at Zia Maria Chelsea, a family-run Italian restaurant. It serves fresh pasta and brick oven pizza, and the thin-crust pizzas are wood fired and made fresh through the day. Share a pizza and a pasta, then linger, since the room is warm and relaxed and suits a long dinner.