New York City · August 17, 2026
New York City
Where I actually go, almost all of it 14th Street and below. Irish pubs, rooftops, and the few dinners I bothered to book.
14 places, 3 nights
My personal bias disclaimers
- I am not a foodie.
- I do not care about, nor do I drink, fancy cocktails.
- I would never take a recommendation from social media.
- I do not believe any line is worth waiting in. Walk in culture only.
- I don’t really like to go out on weekend nights because there are too many people.
- I exclusively hang out “downtown” Manhattan, which is from 14th Street down to the Financial District. If you’re within these neighborhoods you better give me a call to get a coffee or a beer.
The greatest thing to experience in New York City is the people. Sightseeing, cuisine, bars, museums, shows, and nightlife are merely used as an excuse to get out to see, meet, and interact with the people that make NYC great.
I’m convinced Irish pubs are the great equalizer of the world. Everything from the working man to the world’s elite drink at Irish pubs across the world. When I am in far far far away lands, I always find the nearest Irish pub or tavern, because I always feel at home.
A night in the Financial District
The tightest night on this list. Dinner, a pub and the best rooftop in Manhattan are all within a six minute walk of each other, and the two best rooftop bars in the city are both here.
Harry’s
1 Hanover Square, New York, NY 10004 · Financial District · Dinner, book ahead
Old money vibes steak house, sexy restaurant, sexy bar, overall solid place.
Ulysses
58 Stone St, New York, NY 10004 · Financial District · Irish pub
At some point you will find yourself in the Financial District, so you’ll want to go to Stone Street, and this is where I would start. Solid bar food.
Manhatta
28 Liberty St, 60th Floor, New York, NY 10005 · Financial District · Rooftop
This bar is indoors, but has an amazing view. I’ve almost always been able to just walk in and get a seat at the bar.
Overstory
70 Pine St, 64th Floor, New York, NY 10005 · Financial District · Rooftop, book ahead
In my opinion this is the GOAT of rooftop bars in Manhattan. If you’re going to go, I recommend making a reservation here, especially on the weekends.
A night in Soho, Nolita and the East Village
Everything here is inside a thirteen minute walk. Dinner on East 2nd, a pub on Spring Street, and two hotel rooftops on the Bowery that you can nearly always walk into.
Supper
156 E 2nd St, New York, NY 10009 · East Village · Dinner, book ahead
Old school Italian spot, cash only. The food here is amazing. When I had my company’s whole team in town this is where I hosted our team dinner.
Beyond the Pale
53 Spring St, New York, NY 10012 · Soho · Irish pub
BTP is so great I have its logo tattoo’d on my ass. Owners are very nice, properly Irish, and made me feel at home when I first moved to NYC. Solid bar food.
Public Hotel Rooftop
215 Chrystie St, New York, NY 10002 · Lower East Side · Rooftop
This is a sexy hotel. Ladies are obsessed with taking pictures on their escalators??
Citizen M Hotel Rooftop Bar
189 Bowery, New York, NY 10002 · Lower East Side · Rooftop
Really nothing special about this spot, other than it has good views, you likely can find a seat or table, and you can always just walk in.
A night in the West Village
Dinner in Meatpacking and then a pub on 7th Ave South, about a ten minute walk apart. The West Village is a great going out spot in general, so this is more of a starting point than a route.
Mēdüzā Mediterrania
657 Hudson St, New York, NY 10014 · Meatpacking District · Dinner, book ahead
Very sexy restaurant, food is solid. Definitely paying for a combination of aesthetics and good food here.
TAO Downtown
92 9th Ave, New York, NY 10011 · Meatpacking District · Dinner, book ahead
Another sexy restaurant. Food and aesthetic are both great here. Just a heads up, TAO isn’t just an NYC thing. They have one in Chicago and Vegas as well. Asian food.
The Galway Hooker
133 7th Ave S, New York, NY 10014 · West Village · Irish pub
Won a $50 gift card at trivia here, mainly why it made the list. However, the West Village is a great going out spot, and this is a really solid place to use as a go to within the neighborhood.
Worth the walk on its own
Three places that don’t fit a night with anything else, which is not a knock on any of them.
The Ear Inn
326 Spring St, New York, NY 10013 · Hudson Square · Irish pub
Proper Irish spot. I think it’s one of the oldest bars in NYC (I feel like multiple places claim this title). The owner has a great story of him during Hurricane Sandy, guy was really going to go down with the ship. It was originally right on the west river before they added to the island of Manhattan. Solid bar food.
It sits out on its own at the far west end of Spring Street, a good twenty minutes from both the Soho night and the West Village night, so go because you want to go to the Ear Inn.
Keens Steakhouse
72 W 36th St, New York, NY 10018 · Garment District · Dinner, book ahead
Breaking my rule here and going out of downtown NYC. This place is a really cool old school steak house. They have smoking pipes from every iconic person in NYC history. Bar is really cool.
The Arlo Hotel Rooftop
96 Wythe Ave, Brooklyn, NY 11249 · Williamsburg, Brooklyn · Rooftop
I’m not a big Brooklyn guy, but this hotel has to have the best views of Manhattan. If you want to see the Manhattan skyline, you have to be off it, so this is the trip across the river.
Anywhere marked book ahead is realistically $100 per person once you’ve had food and a drink. Everywhere else on this list is walk in.
