Trip tips for a long weekend in New York

A long weekend in New York City has endless possibilities, but if you’re on the hunt for a different experience blending genuine wines, soulful food, and live music, here are some can’t-miss spots. From upscale Park Avenue lunches to intimate jazz sessions, this guide will help you savor NYC’s best.

1. Park Avenue 425 - Business Lunch with a Twist

What to Expect: If you’re up for a business lunch that’s all about sharing, Park Avenue 425 sets the perfect stage. In a city where hustle never stops, this spot offers a refreshing way to mix business with pleasure. Sharing plates let you sample a variety of flavors, which turns a working lunch into an experience.

Must-Try: The burger here isn’t just a burger—it’s served with a rich, juicy dipping sauce that adds layers of flavor. On the wine side, Park Avenue 425’s selection will impress even the most discerning palate. My host knows me well and opted for a bottle of Quintarelli Valpollicella DOC 2017, for its rich Italian flair, passing through a Ramey Cabernet Sauvignon from Napa Valley, and ending with something special, the 2009 Colheita Madeira  by Cossart Gordon.

2. Ivan Ramen - For the Ramen Enthusiasts

What to Expect: If you’re a fan of Chef’s Table on Netflix, you’ll know Ivan Ramen is a pilgrimage spot. Ivan Orkin’s ramen goes beyond the ordinary with rich umami flavors and inventive dishes that keep it authentic yet unique.

Must-Try: Ivan’s Bao with pastrami offers a bold twist on traditional bao, while the tuna tartare with spicy cucumbers has a refreshing kick. Don’t skip the Ramen, a signature dish packed with deep flavors. Pair it all with their house sake, or an unfiltered one if you really like to experiment, to complete the experience. Ivan Ramen is the spot for serious ramen lovers seeking inventive, bold flavors.

3. Ops Pizza - Casual Pizzas & Great Drinks in Williamsburg

What to Expect: For an unpretentious yet delicious pizza experience, head to Williamsburg’s Ops Pizza. This Brooklyn gem, recommended by locals, has built a reputation for its rustic, flavorful pizzas and an impressive lineup of drinks.

Must-Try: Their Margherita pizza paired with Biere Vivant Bitter Orange by La brasserie des voirons is a simple but unforgettable combination. For those who love exploring drink options, Ops also offers unique natural cider and wine selections that perfectly complement the pizzas. The vibe is relaxed and cozy—ideal for a laid-back afternoon or evening with friends.

4. 7th Street Burger - Where Flavor Meets Simplicity

What to Expect: Sometimes, all you want is a no-fuss, crave-worthy burger, and 7th Street Burger has you covered. Known for its smashed burgers, this joint has quickly become a local favorite.

Must-Try: The classic smashed burger is rich, juicy, and, yes, a bit greasy—in the best way possible. With options for vegetarians, everyone can join in. 7th Street Burger is the perfect quick stop to refuel as you explore the city, and you’ll find various locations around town for added convenience.

5. Ten Bells - Natural Wines and Refreshing Simplicity

What to Expect: Wine lovers, especially those into natural and organic wines, will love Ten Bells. Located in the Lower East Side, this cozy bar was recommended by locals and has a loyal following thanks to its straightforward menu and impeccable natural wine selection.

Must-Try: Grab a glass of their featured natural wine or cider, and pair it with something simple from their menu. The minimalist offerings let you focus on the quality of the drink and the ambiance. This is an easy-going place for pre-dinner drinks or an early night out.

6. Smalls Jazz Club - A Jazz Lover’s Paradise

What to Expect: Smalls Jazz Club in Greenwich Village is where the city’s jazz enthusiasts come to get their fix. Known for intimate sessions and an open stage for musicians, this is where you’ll find some of the most authentic and spontaneous jazz in NYC.

Must-Try: Plan to stay late! Smalls often reserves the best for after-hours, where talented musicians take the stage in impromptu sessions. The vibe is unpolished and genuine, allowing the music to take center stage. Get a drink, settle into a spot, and let the jazz carry you through the night.

7. Union Pool - Soulful Mondays with Reverend Vince Anderson

What to Expect: If you happen to be in NYC on a Monday, Union Pool in Williamsburg is where you need to be. Reverend Vince’s Monday night play is legendary, combining soulful vibes with audience interaction. Regulars and new fans alike gather to see Vince and his talented lineup of musicians, including talented artists like Jaleel.

Must-Try: Grab a drink and let the music speak for itself. With an eclectic crowd, warm ambiance, and some of the best soul music in the city, it’s the perfect end to a Monday. It’s a laid-back yet memorable way to experience Brooklyn’s music culture, so just enjoy the moment.

Final Thoughts

NYC has something for every palate and every music taste, and with just a few days, you can get a fantastic sampling of what the city has to offer. From upscale lunches to ramen, pizza, jazz, and soul, this itinerary brings together some of the best flavors and sounds.

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