A Stroll on the Highline and Tacos

Meet your SO near 30th and 10th Avenue and begin your walk down The Highline towards Chelsea. When you arrive at Chelsea Market, take the stairs down and grab tacos at Los Tacos No. 1. If you fancy a cheeky beverage, Tacos No. 1 doesn’t have alcohol, but you can snag a drink at Los Moriscos next door (part of the beauty of a food hall market). We’d recommend a Paloma or marg. After you scarf down a taco… or three, walk over to Pier 57 and watch the sunset on the rooftop park. Alternatively (or additionally), you can walk over to Little Island for one of their intimate concerts. Many of the concerts have been free this summer. Check out the concert calendar link here.

Museum of Photography and Ice Cream

Make your way to Fotografiska in Gramercy. With no permanent exhibits, Fotografiska always has something new and different– great for museum aficionados and beginners alike. The museum is open Sunday to Wednesday until 9pm and Thursday to Saturday until 11pm. With these hours, you can really have your own night at the museum. In addition to its late hours, Fotografiska is unique in that it allows guests to purchase cocktails and wine in the lobby which they can sip on throughout the museum. Sounds like the sweetest evening ever, though we’ll suggest just one more stop (but only if you’re out Wednesday-Sunday, when this spot is open). A couple blocks south, you’ll find Caffe Panna – ice cream and soft serve inspired by Italy. With flavors that pay homage to traditional Stracciatella, comforting peach cobbler, and even Caprese salads, you’ll be sure to wow your other half.

Tram Ride and Sunset Cocktails

Head on up to the Upper East Side. At 60th and 1st avenue you’ll find the entrance to the Roosevelt Island Tram. For the cost of a subway ride, you’ll fly high in a red cable car on a telephone wire across the river and arrive on Roosevelt Island (a small piece of land between Manhattan and Queens). While the ride is quick over the Queensboro bridge, you’ll still get a great view of the East River. There isn’t much on Roosevelt Island, but the Panorama Room itself is worth the journey. Located on the 18th floor of the Graduate Hotel, the Panorama Room boasts giant floor to ceiling windows giving you an epic vantage point of the city. We’d recommend going at sunset or later in the evening to see the twinkling cityscape. Unwind with your date while you both enjoy a tasty cocktail or mocktail. Remember, you’re paying for the experience.

Burgers, Fries, and A Speakeasy

Head to Five Guys (yes, Five Guys – read on to know why!) on Bleeker Street in the West Village. Order the Patty Melt and a milkshake from the secret menu. If you’re feeling adventurous, try the Elvis—a bacon, banana, and chocolate concoction. If you look around, you’ll notice girls in heels walking through the restaurant toward a bouncer and staircase. Upstairs is The Garrett—a speakeasy located inside the Five Guys. Once you’ve explored the bar, had a Negroni and gone to the bathroom (it’s pretty cool), you can end the night a block away at Cellar Dog. Cellar Dog is the new Fat Cat, but other than the name, nothing has changed. You can play shuffle board, ping pong, pool, fuse ball, and more while sipping on a beer or cider to end your evening.

Trendy Wine Bar and Pizza in Williamsburg

Ready for a laid-back night? Take the L to Sauced in Williamsburg (or Uber, we’re not judging). Sauced sounds like a pizza place, but it’s actually a wine bar with a charming outdoor patio (don’t worry, you’ll get pizza later). Split a bottle of orange wine and a charcuterie board. Once you’ve worked up a real appetite, head on over to Fini Pizza. Trust us, it’ll probably become your new favorite. Try the white slice with lemon! You won’t regret it. Bonus: If you’re heading to Williamsburg for a daytime date instead, take the ferry, and go to the best outdoor food market, Smorgasburg. Sit on a bench with your person and enjoy oxtail nachos or tuna tostadas in Marsha P. Johnson Park on Saturdays and Prospect Park on Sundays.

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